The Boyfriend Quest

For cuckoldresses and the men who serve them.
Cuckcuckgoose1
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Re: The Boyfriend Quest

Unread post by Cuckcuckgoose1 » Fri Oct 11, 2024 9:54 am

Tap wrote:
Fri Oct 11, 2024 9:13 am
". . . his performance anxiety is completely gone, she said he is large and has great stamina. She said they fucked all over the house in each room and she is truly enjoying being filled up for the first time in her life."

Uh-oh.
She'll probably navigate through the motions, and emotions, of a NRE. Let it run its course, steady as she goes.

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Re: The Boyfriend Quest

Unread post by Rogueuser1 » Fri Oct 11, 2024 11:43 am

Amazing! Hopefully all 3 of you have a great time and all of your plans work out!
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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Fri Oct 11, 2024 12:00 pm

I had my very first cleanup this morning!

They were in the room together for about an hour and a half. At one point past the halfway mark, I heard him cum. I was going about my morning routine having a shower and shaving, and intermittently listening at the door, which is closed. I could hear her cum and lots of chatting. Eventually, I heard them talking and get up and I met her in the hallway.

She pulled me into the room with a knowing smile and closed the door. she pointed to her thighs and I could see cum running down them.

I just started grinning and saying all sorts of crazy stuff. I laid her down in bed and as I spread her knees up, I saw a rivet of seaman run down each thigh. I snapped a quick photo and started cleaning up her pussy and thighs.

S was in a rush because he had gotten up and was moving around in the living space. I asked her to sit on my face and she did. I was full of adrenaline running through my body and was jacking off as fast as I could. I came in about a minute and she crawled off. It was very surreal.

When I first approached her and she pointed down, I could smell the smell of semen. The taste was not the same as mine completely different. My head is still spinning. I’m at my examination at headquarters trying to keep my head in the game, but it’s very hard

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Sat Oct 12, 2024 5:15 am

Holy cow, what a crazy last 24 hours.

Before I get to that, I want to circle back to something that she had told me about when she and Dave first arrived at the house on Thursday. They explored every room with him going inside of her. In addition to the living room and bedrooms, he bent her over the kitchen counter and fucked her for a while as well as laying her down on the table.
Her words were “it was amazing to lay on the table and get railed”. I thought that was very hot coming from my own wife!

Picking up from yesterday after the cream pie clean up, I came out to the kitchen and made them coffee and myself a quick breakfast before I had to go. They went out to sit by the pool as I finished up and got ready to go. I went out and said goodbye and S followed me back into the house .We had a quick moment in the bedroom. We had a couple of things we needed to clear up and I held her for just a minute before heading out.

I spent my day in the boardroom with about 20 other people working on our project. It was very hard to concentrate and my angst was slowly building over the morning. S checked in several times with me by text and Dave sent me a couple of shots of her nude by the pool as well as a picture of her backside as he fucked her in the spare bedroom.

About lunch time I talked to her on the phone because I just needed to hear her voice. She realized where I was at and started talking to me for several minutes. This was a good reset for me and I went back into the afternoon with The angst building stronger than the morning session. About 2:00 p.m. I snuck out and called her again just to hear her for a couple of minutes. She said she was having an amazing day in the pool, sunbathing nude, making food, and she said “some other fun things”. Her and Dave were arriving at headquarters at 4:30 in advance of my physical examination so I only had a couple of hours to go.

The group broke up at 4:00 and I got changed and ready to go. I was stretching and prepping for my exam when I looked up and saw her coming through the door. There were about five other people in the room so I had to have a modest hug and a couple of kisses. It was very fun to feel that she was wearing no panties under her sundress. I greeted Dave and introduced him around as our good friend who is a professional photographer. My boss was very happy to meet him and wanted to know about how he and I had met. Fortunately, we'd come up with a plan and cover story ahead of time and we seemed to pull off well.

My test went very well with my promotion secured and a great weight off my shoulders. The physical exertion of the exam had reset my head and I left in a great mood. S had agreed that she would ride with me back to the house so we had a nice time chatting and talking over the night ahead a little bit.

She said she would make dinner, we had brought down some local seafood and so while she was doing that, Dave and I poured some whiskey and had a quick shot. I got changed and jumped in that cold pool and did a couple of laps. He and I sat poolside with our cocktails and watched S through the window as she was working in the kitchen. We had many great conversations over the next hour. Dave doesn't normally drink and so he got very loose and chatty, both exactly what we needed. S serve dinner next to the pool and we had a very nice meal with the moon rise. This was a nice break for me as normally I would have been cooking.

We got everything cleaned up and put away and I settled down on one end of the couch, There is an L couch in the living room and we had piled pillows and some blankets on it yesterday. I made a spot with my head to the L intersection facing away from the other side of the couch. Dave sat down in a facing chair and we chatted for a while. All conversation stopped when S came out in a black lounger set that she had recently gotten from VS. It was funny to watch because he turned into a little schoolboy as soon as he saw her. She directed him to come and sit on the couch and they cuddled and talked. I stayed engaged in the conversation although I was facing away from them.

I had put out some red, LED stringlights so there as a great mood in the room.

This went on for about 45 minutes with them changing positions. They ended up with her straddling him and she started grinding on him. He pulled her boxers down and I could see him slip into her. they rode for a little while and then laid back and snuggled. It was very nice to be closed to them and I got to rub her foot discreetly. At one point as they laid near my head, we held hands and I kissed her fingers. I was drifting in and out of sleep as I was exhausted from the last two days. the last thing I remember was them drifting off to sleep.

I woke up about 1:30 and saw the couch was empty. I went to check on them and the door was open with a LED candle lighting the room. They were sound asleep and I could hear the snoring through the door way. I checked again on them about 2:00 and got to see them shift in their sleep positions, both of them waking up just enough to say sweet things to each other before drifting off.

At about 3:30 S came out to check on me and we both laid on the couch together naked under a blanket. I held her for about 30 minutes while she slept and then she woke up and we talked for another 15. I told her that I was feeling like I was in a good spot and her and I got caught up from the evening’s conversations that Dave and I had. I told her she should go back as the couch was not well suited for two people laying down to sleep.

She went back to him and I looked in after about 10 minutes to see a heavy make out session starting


What transpired next was my first true Cuck experience and one of the hottest moments of my life yet!!

The layout of the house allowed me to stand inside the guest bath doorway with a direct view of the entire bed. They were under the covers talking and doing all sorts of things resulting in her making some very sexy sounds. She got on top of him as bed sheets started working off of her. I could hear that she was building to an orgasm and I saw her mount him and start riding.

Up to this point, every time that I'd watched or listened, my cock had never got erect. However this morning it was rock hard as I watched them. All the negative feelings were gone and I was super turned on as well as a little jealous with some angst going. It was amazing to hear the words that she was saying to him and moving her body. After a while, he moved her over on her back and worked her pussy while talking to her. About this time I looked up and caught my reflection in the mirror, it was the quintessential cuckold moment. The one thought that was going through my head as I wish I had a chair to sit inside could relax, maybe with time :-)

She remounted him. I had a huge amount of pre-cum showing up and eventually, I finished. They were snuggling on the bed I quietly left and made some coffee and write this.

This morning, S and I will be at headquarters and Dave driving home to do some chores. S and I are planning to duck out of a late morning class to go to a coffee shop and meet up with dave about 3 for a walk. We are planning to go to dinner this evening
Last edited by jaydub on Thu Oct 17, 2024 9:16 am, edited 1 time in total.

Cuckcuckgoose1
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Re: The Boyfriend Quest

Unread post by Cuckcuckgoose1 » Sat Oct 12, 2024 6:05 am

Oh my S is going to be so worn out after this. Glad this is working out for you. Any thoughts on a threesome together so you get to enjoy first hand your wife being penetrated by another man?

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Re: The boyfriend quest

Unread post by leggysman » Sat Oct 12, 2024 8:37 am

jaydub wrote:
Fri Aug 23, 2024 3:01 pm
One of the main points that we all seem to be working on is my role in next weekend's encounters I have always dreamed of being able to be in person and witnessing S getting fucked for the first time. Remember she has never been touched by another man and this is going to be a very special moment. However, Jay being a nonkink type of person was very hesitant to even have me in the same house during their escapades. S also felt very strongly that she could not have me in the room. This kept me high with anxiety and I couldn't sleep at night. We need to talk this out and make a plan for everyone to feel good.

On Thursday I reached out to Jay, who is about an hour and a half away from the company headquarters and we agreed to rearrange our schedules and meet up in person on Friday before I flew home.
This is confusing, like you meant Drew/Dave but typed your own name instead? Six times in that post?
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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Sat Oct 12, 2024 10:21 am

Yes that is correct my mistake

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Re: The Boyfriend Quest

Unread post by eater » Sat Oct 12, 2024 12:06 pm

great story. congratulations.

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Re: The Boyfriend Quest

Unread post by venus-can99 » Sat Oct 12, 2024 12:54 pm

Hope all 3 of you are having fun. Thanks for sharing the experience

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Sat Oct 12, 2024 5:25 pm

In all the ups and downs and excitement of yesterday, I completely forgot to mention they did anal!

S said it went really well and felt great. She said it was completely different than the smooth small dildos that we had tried before.
She said she really enjoyed it although they didn’t do it for too long. I am totally floored. Never once did I think this was an option!

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Re: The Boyfriend Quest

Unread post by venus-can99 » Sat Oct 12, 2024 9:08 pm

Oh wow! Glad to hear it went well and she enjoyed it.

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Sun Oct 13, 2024 5:09 am

We had an amazing morning together. About 6:00 a.m, I went into the bathroom and took a shower. The bathroom door to the guest bedroom is right next to the master bedroom. After my shower, I cracked open the door whiIe I shaved and got ready for the day so that they could know that I was around and I could hear them talking and giggling, but not making anything out. When I was finished, I stuck my head in the open door and said good morning. S out a little noise of surprise and started laughing and they both said good morning. I asked them if they were ready for coffee. Dave answered immediately with a yes.

I went to the kitchen to start the Keurig machine, S was immediately up and in the kitchen. She said she would take the coffee in when it was ready. She said they both were confused by what I asked. Wondering if I was going to bring it into the room to them. I said I would be happy to do that, but she thought it would be too much for Dave having me come into his bedroom. Within the next couple of minutes Dave came out and and sat down at the breakfast bar. He was just wearing a pair of shorts and no shirt.

I was very encouraged because this showed that he was taking another step in being comfortable around me. S and I took the seats next to him and they snuggled while they had their morning coffee. We talked about all sorts of different things and made a plan for the day.

We were all surprised when we saw that there was just an hour left before S and I needed to start the drive to headquarters. She told me that they were going to go and take a shower together and get ready for the day. I want her that we only had so much time before we needed to leave the house. Dave laughed and said that he would help wash her so they would go faster. I smiled it and told him that most likely that would only make things go longer. We all chuckled and they headed out to his room. S finished getting ready after her shower and we loaded up the car for the drive. Dave left at the same time, he was heading home to do some work and then would meet us at a park for a walk in the Afternoon.

We had a good drive and started our conference. This was an event that we needed to make an appearance at, but not necessarily involved with. We stayed through the opening session and then headed out to a coffee shop. We got our drinks and went outside to sit in the morning sun. We had some small talk conversation, but S was feeling the effects of two nights of not having good sleep so she was a little down with low energy and not too chatty. We decided to head back to the house so that she could have a short nap and a dip in the pool and then go back to the event after the lunch break.

She laid out in the sun nude for a while before dipping in the pool. I snapped a couple of photos and sent them to Dave. We had snapped a selfie of the three of us before leaving that morning, so I sent it to him and he asked if he was a good time to send some R and x-rated photos.

They came through and they were very beautiful featuring my favorite subject in each. I made lunch and we ate, we had a discussion about where I was at emotionally. We were both very happy that it appeared that I've turned a corner in the last 24 hours . I told her that we needed to talk about our Christmas break vacation plans in regards to wanting to talk to him about. I am still a little hesitant about how it's going to work, but we have got our tickets and rent a car for the drive. We will have seven nights in Palm Springs and I'm a little unsure about the length of a time and the intensity of the situation, But we both agreed that Dave needed to have a date range so that he can start working logistics on his end and that we would work on the details of his stay later.

I reaffirmed to her how amazing the cleanup had been and I wanted to be sure that my need for that stayed fresh in her mind because I didn't want to nag or push about it but I needed to have confidence that she was on the lookout for those opportunities. Dave has been having a return of some of his performance anxieties so the next opportunity is a little unknown.

We loaded back up in the car and returned for a short afternoon session. I knew of a amazing River Walk about 10 minutes from headquarters from a prior visit so I sent Dave a pin to the parking lot and agreed about meeting at 3:00 p.m for a walk. Dave said he was editing the pictures he took from my promotional exam the day before and would bring them back with him.

We both got changed into casual clothes with S putting on a skirt because we both knew what they wanted to do in the park. He was bringing his camera with him and we were happily anticipating some sexually charged photos of them.

A short drive later, we pulled into the parking lot next to his car and got out. I snapped a very fun picture of them embracing and kissing standing outside the car with me shooting through the car window.

On a side note on their emotional connection and relationship is definitely deepened even more over this weekend especially with them actually having intercourse. There has been a change in S that I've noticed especially the way that she looks at him and it always been loving, endearing, and deep before but now there is even more intensity to it. We while we had talked about all this before and we are all well grounded, however in the situation still has my attention and we'll talk about it a little bit more in the future once we get clear of this weekend. there is no worries on my end about the boundaries of the three of us together and I know a lot of it is just NRE. but it is triggering some angst and insecurity in the cuckold realm.


We all walk down the short path to the foot bridge across the river, we stopped to take some photos. We continued our walk as there was lots of people around the bridge and not a good spot for hanging out for the things that we wanted to do. We walked about an eighth of a mile down the path with them stopping to make out and him feeling her butt whenever there was a gap in people walking. I had spied a small footpath to an opening that had some large dead fall trees. It looked like an amazing spot for some photos that was a little bit more private then the other areas.
We walked over and I offered to take pictures. Dave set up his camera and I snapped away as they made out. I was in a great spot to be able to see the approaches to where they are at and told them just to enjoy each other and I would make sure that we are not seen. I got some incredible pictures of them making out.


He had pulled her skirt up and was playing with her ass and fingering her pussy. I asked him after a while to spin around so her back was to him facing me and we got some highly erotic photos of her looking at the camera, leaning back against him with her arms around his neck while he fingered her. Ask her to bend forward and arch her back and she did so grinding on him.

I spotted another fun section of the downtree and we moved a little bit over so that he could set her up on the trunk. It was a fun situation because it appeared that he had mounted her and was fucking her on the tree. We had several times that I could see dog walkers coming so he paused and chatted together as they passed. We resumed our walk with several more pauses for some very sexy photos. Everyone was very relaxed and joking and laughing and talking as we went.

As we walked, whenever I got the opportunity when he was not looking, I rubbed her back or touched her in some way. I had always thought that it would be very fun for her to go for a walk holding the hand of her boyfriend on one side and the hand of her husband on the other. At this point still we both knew it would be too much for him, but there was a time that we had to scrunch together to let another walking group pass and I held her hand for about 10 seconds as we all walked together. it was a very touching moment.


Getting back to the bridge I offered to take a couple of more pictures which I did and then he immediately asked for the camera back and started taking some pictures of her eyes. We got an interesting look for a lady passing by as she'd seen that I was taking their picture and that had he had abruptly taken the camera back. Kind of something fun.


It was getting on about 5:00 p.m. and the plan had been to go back to the pool for a little bit before going to dinner, but we were all hungry and the place that we had agreed to go was just a couple miles away from where we're at. We headed out with S riding in his car I pulled into the parking lot and they parked a couple cars down. I had to wait for them for a while as they were making out and then we all walked in the restaurant and got a booth. We had been positioned well so that again I could look out as they enjoyed each other. I snapped several photos above and below the table as he played with her pussy and she rubbed his cock.

We had a very nice dinner together and walk back out to the cars. I told them that I would meet them back at the house and they started making out next to their car as I pulled out. As I exited out on the road I had to drive past them on the service road and made eye contact with us and we both smiled. Getting back to the house I did a couple chores and tidied things up. I could see on our app that they were on the way back and they arrived about 15 minutes later.

They were both giggling and a little embarrassed, they had gotten in the car and Dave had leaned over from the driver's seat and started eating her pussy for a while. She had closed her eyes to enjoy it and when they both looked up, a car of senior citizens had pulled in next to them and the elderly driver had gotten out.

Dave was pretty embarrassed because the man had a high angle view of what was going on, although he didn't think that he had actually seen anything.

I have to think about the situation a little bit because the car was parked directly in front of the tinted windows of the restaurant. One of the areas that I have felt that I can help them in is being on the lookout or giving some realistic suggestions about the area or situations that they're in. They had both got caught up in the moment and were extra horny and may have pushed into a situation that could have been not great for people who happen to be in the area. I made mental note to chat about later with them.

We were all ready to unwind and agreed that we would like to have another round of cocktails as we have the night before. I reminded S that we need to call our children before we got to far into the evening. We set up outside by the pool and had a very nice video call with our three kids. l Dave set up his computer and got ready to transfer the photo files from my exam to me. After the call I asked S what the idea was for the evening and she said they were talked about making cocktails and then going to the third bedroom for some fun together. I asked her to make sure that the door stayed open and she assured me that she would.

While they got settled in, I made sure that the lights are off in the living area as I didn't want to be backlit and have him see me. I watched through the small crack in the door that looked directly onto the section of bed that they were on as they made out. I have always felt bad about being sneaky and watching them and so I decided to be a little bit bolder and help continue to turn the situation into more something more relaxed as it had been going this direction over the course of this visit. I quietly went and got a chair from in the kitchen and brought my cocktail with me back. I also took off all my clothes and got comfortable on the chair. it was a really nice feeling to be able to relax in the seat and sip my drink while I watch them. I didn't get immediately hard as I had this morning, but as I worked on my cock it responded well.

In the room she had mounted him and it was obviously she was try to work on his cock going. The entire time they were giggling and laughing and whispering to each other.

In past posts I have referred to them fucking or her getting fucked. However in reality it is never been a purely sexual encounter. It is always a close, loving, but emotionally intensive love making session and this was no different. He was obviously having issues getting erect and he moved her on her back and started working her pussy for a while. They were talking and whispering and it was very beautiful to watch.

After a little bit of time, he worked his way down and started eating her out. She responded with lots of vocals and at one point even wrapping her legs up around his head. She was obviously heading to orgasm and I was very excited because I had never seen her come with another man.
I'd only heard S cum through the door or through the walls. I was also building up and I paced myself so that I could come at the same time that she did.

After several buildups she let loose with a truly intensive orgasm that I've only seen a few times before. It was a truly incredible and beautiful, I was so grateful to have been able to see it. I clean myself up and sat back with my cocktail as they shifted positions. She sat up and put some lube in her hand and started working as cock. After a while it was obvious that it wasn't going to be functioning as they both were hoping. I took the opportunity to put the chair in the cocktail away and started doing some things in the kitchen. I went back to check on them and was surprised to find them in a 69 position.

I have always wanted to watch my wife suck a cock. I have a picture from our last encounter that he had sent me of her on her knees that I find exceptionally hot. I had watched her from a distance suck on him but I couldn't actually see too much. Her head was facing the door so I could tell exactly what she was doing but in the low candlelight, I couldn't see anything because the area that she was connected with was too dark for any details, but I could hear her at work and I knew exactly what he was feeling.

S is amazing in her blowjobs, something that she has newly acquired in the last couple of years. I knew exactly what he was experiencing. Unfortunately his issue persisted and I could tell they were getting done. They chatted about hearing me outside the door, I had not been too quit and they had heard me. She spend time reassuring him and keeping things on track. I went back to the living room

Behind The L couch in the house is a small sitting area with two very comfortable swivel chairs. He came out with just his shorts on and she came out wearing the t-shirt that he had given her.

She sat down in his lap and we had some great conversations. They had taken their cocktails to the room and hadn’t worked on them at all, so they sipped and he showed us pictures on his phone of his military service which was very impressive. After that cocktails kicked in she got pretty playful. moving her body around in different positions. At one point we both had our phones out videoing her, but from two different perspectives.
Throughout this time I had a big smile on my face and when we had moments of prolonged eye contact with S, I would move my head and smile even more to let her know how much fun. I could see her face glowing with happiness. We are both very grateful that I've turned this corner and we're having fun. She's feeling a whole new level of love in her life from her husband and her boyfriend now both at the same time.

It was time for dessert, so we moved to the breakfast bar in the kitchen while we dished up and ate. At one point she passed by and paused next to me and I put my hand on her butt at the same time he put her hand on the butt and our hands overlapped. We both started laughing and I made a funny comment about interference :-)

All of us seem to really enjoy getting to the spot of being a more comfortable and relaxed around each other and enjoying the situation more. We talked for about another hour. He said he was going to go get washed up and ready for bed. S and I moved to the couch and sat by each other and snuggled a little bit. He came back out to the kitchen a couple different times for things and each time she heard him coming, she scooted away from me a little bit. which I was okay with because it felt like the right thing to do.

Then he came and sat down on the opposite side of the couch and she got up and went to him. They stayed like that for about 2 minutes before they both got up and walked to the bedroom. I cleared the dishes in the kitchen and as he disappeared down the hallway he said to me to have a great night.

I went and got washed up and looked in their room. She was already riding him. He was evidently was up in full force and she was enjoying being completely full. They were in true love making mode until they both got worked up and he grabbed on to her hips and really started fucking her.

I then witnessed the most erotic, beautiful, gorgeous, heartbreaking, scary and devastating event that I had ever seen in my life. She let loose with a massive orgasm the likes of which I've never seen before in my life.

As she peaked and started going down, a second one hit, which is extremely rare for her. This one not was quite as powerful as the first, but big nonetheless. He came shortly after that and I watch them collapse into each other's arms.

I came very hard at the same time as she did and as I clean myself up for the third time that day, I could tell that they were both going to sleep as all three of us were exhausted.

I came out to sleep on the couch which I had previously told S that I would do. For some reason I prefer sleeping on the couch in this situation. I went right to sleep as I was exhausted and had a couple of cocktails.

I woke up at 2:00 a.m. and went and looked in on them, they were both sound asleep. I was able to go back to sleep until 3:00 when I woke up and checking in on them again. still sound asleep so I started writing up this posting.

I was having a pretty tough time in my head since waking up with the gravity of what I saw last night in addition to how I had seen S look at him yesterday. I just really needed to hold her and have some time.

At 4:00 I looked up from the computer, I was sitting on the floor in front of the couch writing and she walked through the hall. She still had her eyes closed from sleep and I literally ran across the room and grabbed her and told her I needed her so much. She said we were going to the couch and she lay down and immediately opened her legs for me to eat her pussy.

I lay down and started licking and sticking my tongue inside of her, it had been about 5 hours since he came in her and there wasn't really anything left except their combined aroma and taste which I enjoyed. I then crawled up and we held each other I told her I had to rough start of the morning and how much I just needed to be with her.

I even cried a little bit and she held me and we talked about our love and how much we appreciated each other in this situation. It felt really good to reconnect with her and after a little bit of time I started rubbing myself on her leg as my angst was replaced with horniness.

She had me sit up on the couch and she got on top and ground on my cock, which was not hard at all, but felt really good. After a little bit of time I got enough of an erection that she was able to work it into her pussy and she continued to ride. My orgasm was a little elusive and I worked hard at it as she played with my nipples. She let me come inside of her and we held each other for a few more minutes she said she was going back to bed. She got halfway to the hall and came back and kiss me some more.

She went to the bathroom and I heard her crawl back in bed and I sat back down to right thinking that they would be going to sleep. I started hearing some sounds that I assumed was them talking and I went and looked in just as he unloaded in her in missionary position. They were under the covers in the dark room so nothing to see and I enjoyed the sounds.

As I finish this up and enjoy a cup of coffee and a sunrise coming soon, I'm contemplating the day.

We have not too much planned. We're going to take a drive about 30 minutes to an Apple Festival and get some donuts.

You'll remember that we have wanted to have a drive where I'm in the front seat chauffeuring them and they're in the back fooling around and so we specifically got a four-door SUV for this trip so that we could do that. We still have a lot of food to eat in our kitchen and the temps are supposed to be in the 80s today so definitely some pool time.

They have been contemplating their upcoming time apart, as it won't be until Christmas break that we get back together again. We'll have a conversation about that trip and travel today. I still have some anxieties about it, but I'm sure we will figure it out.

I realized this morning how important writing this down is for me to process all the things that are going through my head and I appreciate all the encouragement, kind words, and DMS from you guys

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Re: The Boyfriend Quest

Unread post by venus-can99 » Sun Oct 13, 2024 7:05 am

Thanks for this emotional and erotically charged and romantic description of your time with Dave. I love how you describe all your emotinal highs and lows as the day progresses.

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Re: The Boyfriend Quest

Unread post by Cuckcuckgoose1 » Sun Oct 13, 2024 7:20 am

Great update Jay. Thanks for taking the time to keep us informed. Looking forward to more pictures as well.

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Mon Oct 14, 2024 6:26 am

Picking up early sunday morning about 7:00 they got up and came out.

I made them coffee and asked S for a check-in time. We went to the bedroom and I held her for a long time. I asked her if her and I could go for a walk after breakfast as I needed a break from this just for a few minutes. She, of course, agreed and I said I needed to ask her one more thing and I really didn't want to because I didn't think it was fair, but that I needed her to tone it down a little with him and her between now and when we went on our walk. I explained to her that my angst bucket was filled and overflowing and I couldn't manage it. I felt that I could drain it on our walk together enough to have a good day and she agreed.

I talked to about what I had seen last night and told her that I had cum both times. The first, when they were in the spare bedroom with him eating her, I had timed my release to happen with her’s. She was amazed and told me her end of it. (she has a fantasy that includes me eating her pussy while a cowboy jacks off watching her and is begging to cum. She doesn’t let him until she does).

She said this time while Dave was eating her, she was thinking about me watching her instead of the cowboy. She said that in her head, I came at the same time she did.

She went to take a shower and I made her a mimosa and brought it to her. She had a big grin on her face when she saw me through the curtain and kiss me as I gave her her drink. I made myself a mimosa and that helped ground me.

I went to the kitchen and made blueberry pancakes for all of us. When S got out of the shower, she put on a red bra and matching thong and looked absolutely amazing. She came out and sat with Dave at the breakfast bar while I worked on breakfast and we had some good conversations about nothing important. I had a fun moment when s had her elbows on the breakfast bar with her ass sticking out. She hadn't done it intentionally and I was carrying the pancakes spatula; Dave and I both started laughing as we saw what I could have done and I told S that it took all I had to hold myself back from smacking her amazing ass :-)
we all sat at the breakfast bar and ate blueberry pancakes and sausage and made a plan for the day.

After breakfast, we ended up sitting at the dining table talking and looking over pictures on Dave's iPhone. S started getting very sexy with him. As much as I hated to interrupt them, I asked Dave if he had his camera handy. He went out to the car to get it and we started doing an impromptu photo shoot.

As you know Dave is a professional photographer and his cameras are very high-end and have the ability to deliver exceptional photos. I started clicking away and S did a very good job of holding her conversation as they looked through pictures on his phone.

She has always been very self-conscious of herself and she has had a hard time being the center of attention, let alone having pictures taken of her. This is something she's really been working hard on over the last year with me and she was a champ as we spent about an hour and a half shooting photos in all sorts of different positions. Dave is getting much more comfortable in front of me and was putting fingers in her pussy, pulling on her nipples, and kissing her in all sorts of different positions.
At one point, she leaned forward in his lap and stood up; bent over the table. I watched him spit on his thumb and work it into her asshole.

The look on her face was incredible.

It was fun for me because I could see both ends, the face and the thumb, and captured it well on the camera. They moved over to the kitchen and we did all sorts of other poses. In all, I shot several thousand pictures. Dave is excited because in the coming weeks and months that they're apart, he'll have editing projects to do that will be extra fun for him.

Much to everyone's resistance, we organized ourselves to head out. S dressed in her red shirt and black skirt that she had worn on her very first video call with him. He and I both recognize the outfit and we're very pleased. (You can see a picture of the outfit in the hotties section)

We loaded up into the car, we had a rented four-door Jeep Wrangler that wasn't the best, but we made it work. I moved the passenger seat all the way forward so Dave would have the most amount of room (he is a big dude) and him and S got in the back seat. We had about a 45 minute drive in front of us. I made them agree that if they got hot enough that they wanted to take off their seatbelt, they would let me know so I could find a spot to pull over. Being a retired fireman, I know exactly what a seatbelt can do and what a difference it can make.

We settled in for our drive with them getting very comfortable and making out in the backseat. We carried on a great banter as we worked our way north. They were able to move in all sorts of different positions in the back with their seat belts on.

At one point the traffic slowed to a complete crawl and started backing up so they both unbuckled and S layed down sideways as Dave worked himself down on the floor and started eating her pussy. David took off her red thong and put it over the headrest of the passenger seat. I thought it looked very hot.

I got snap some fun pics and short videos from my vantage point which was very hot. We did this until traffic opened up and they got reset. At this point, S was very worked up and Dave was working her pussy with his fingers, asking questions and getting feedback about what she liked and what felt good. It was getting hot enough that I was looking for a turnout.

We are in a mountainous area with not many options and I was thinking to myself “where is a turn out when you need one”!
Sure enough one opened up I pulled into it fast and parked and they got comfortable and he continued eating her pussy for about 10 minutes.

I got to hold her hand briefly, which is something that I had always wanted to do. Then she put her foot up on the passenger side headrest and I kissed and licked her calf. I was hoping that it would be fun to feel 2 tongues on her body.

Back on the road, we neared the town and the access for the Apple Festival area was backed up and again we were at a crawl. We ended up in a dead standstill for about 30 minutes, So they were able to do all sorts of fun positions in the backseat.

Finally, we started moving and a short amount of time pulled into the venue. We all hit the bathroom. It was a stand alone building and Dave and I went in together. Once we were all back together, we all laughed about that was the first time her husband and her boyfriend used the bathroom together.

We got in line for hot apple donuts and fresh apple cider. It was a long line, but things are moving fast. S noticed that she was by far the hottest dressed female there and she was a little self-conscious of that, but both her and Dave were super snuggly and making out in line. We paid and got our ticket and I said I would stand to pick up our order and they could go and find a spot.

I had asked us when we arrived if we could have a check-in time after we ate because I needed to understand more about the rest of the day and to have her help me move past the spot that I was at. I was also dead tired from lack of sleep and knew that I was not in a great spot to talk to her. I was planning to eat with them and then lay the seats down in the back of the Jeep and take a quick nap to get in a better headspace and get some of my energy back.

She was very agreeable and I got about 10 minutes of sleep which helped me reset. We told Dave that we were going to walk for a check in and we walk to the other side of the field where the venue was. We were not able to hold hands or touch as everyone there had seen her and Dave in line making out and we didn't want to create a weird scene. (However in hindsight this evening we wish we would have done a little something :-)).
We talked about a number of different things.

I told her I was just feeling a little overwhelmed with the angst, not being able to sleep with her at night and the sexual things that I was seeing. I enjoyed them immensely, but it was overloading most of my emotional bank. We both talked about how well Dave was doing and the big jumps forward that he was making in his comfort level with me

He and I had a couple of fun interactions. Yesterday S was putting on her black dress pants which are very tight for our company event in the bathroom, I was in with her with the door open getting ready and Dave was in his room and he could see in. As I walked by I gave her ass a squeeze and Dave said I was just thinking about that. we both laughed at our matching thoughts. Then, over breakfast, we had made reference to our hands touching as we both reach for her ass yesterday and we laughed and said “if you feel hair when you touch her something's wrong :-)

S and I continued our conversation I asked her some questions about how she saw the afternoon evening going as I was trying to prepare myself. I also asked her to help me figure out the sleeping tonight because I was not looking forward to a repeat of the previous night. we agreed to talk about it later in the day. I reaffirmed how much I love her, how proud I was of her, how hot and sexy and how much enjoyment the last couple days had been for me. How grateful for the track that we were on I was.

We are completely surrounded by people and I really wanted to hold her and kiss her, but we contained ourselves and walk back to Dave. We snapped a couple of selfies of her and I for the kids and walked back to the car.

We had passed a microbrew with food on the way in and agreed that that's where we would go for lunch. As we drove the short distance they made out in the backseat. We went in and placed our drink and food order and sat outside on the veranda. It took about an hour for the food to arrive and we talked about all sorts of different things in our lives.

We then started talking about Christmas break in Palm Springs. We shared with him our travel dates and plans and he is going to start working on his coverage for his business as well as his airline tickets

We loaded up and started the drive home which was again backed up by stalled traffic and he and S got busy in the backseat doing all sorts of fun things. About an hour later we as neared our house and they both fell asleep in the backseat holding each other. S had a smile on her face as she slept.

When we got in the house, I asked her for a couple of minutes and we went to our bedroom and I held her and kissed her hard I told her how hot and sexy she looked it was driving me nuts and I really wanted to fuck her. We both affirmed our love for each other and worked to get our swimsuits on so that we could go out to the pool.

We all jumped in the unheated pool. It was refreshing after the day; I immediately got out and started warming up and the chair. They held each other for about 15 minutes in the pool before getting out and we all sat in the sun with S stripping off her swimsuit and sitting in Dave's lap.

We hung out for about an hour talking and laughing about different things. I snapped quite a few photos as he played with her body in different positions.

They went inside to the bedroom and hung out for a for a few hours. I looked in on them occasionally and they were lying together naked on top of the sheets talking.

I could feel myself starting to go downhill as I had been working really hard to keep it together over the course of the day and my lack of sleep for the last couple of nights made it extra hard. Plus the thought of another night by myself on the couch having a hard time sleeping and the discussion of 7 days together coming up all came crashing down on me.

The course of the last couple days were exceptionally hot and fulfilling, but I felt like it was all too much and intense; a result I think of us living together, having the intensity of the sex ramp up, which is a good thing, and the intensity of their love and relationship with each other especially the sleeping part without any break to it had caught up to me.


S came out and I was doing some packing in our bedroom. She could tell that something was up and I told her I just wanted her to enjoy the night and I didn't want to burden her on her last night. She wanted to know what she could do differently about the sleeping situation because I had asked her to help me earlier in the day. I told her not to worry about it and that I was going to get through it. She asks several more times but I insisted that she just have a good evening.

She asked me to come out to the living room so that we could look at pictures together. I really didn't want to because of my mood and I didn't want to bring them down, but I came out and Dave and I and her chatted and looked at photos for a while. I moved to the couch and covered up with a blanket as I was starting to get a little chilly.

They were stretchout facing me on the L couch and I moved my foot over to rub her’s. All of a sudden Dave’s foot jerked back and he said that was his. We all laughed really hard and agreed that there would be some collateral damage!

We were all pretty tired and chatting in low tones. S started giving a rundown of the weekend and how she felt each of us did. Evidently she and Dave had done a lot of talking in their room that night about the things that he was working on. He is still overcoming his performance anxiety, although it's getting better he is still having a tough time.

I do have to hand it to the guy, two months ago he was a vanilla guy that had no idea about any of this Kink and here he is in the middle of it. He also has his own life baggage that he's working through.

We agreed that it was bedtime and made a plan for the hours together in the morning before we left for the airport. Dave said good night and S gave me a hug, she wanted to chat about how I was feeling, but again I didn't want to be the downer too much in her last night so I told her we'll talk in the morning.

We were all very exhausted and I instantly went to sleep. I woke up at 12:30 a.m. and looked on them. they were sleeping very good. I had asked S to make sure that they left the candle on because the night before they had put it in the bathroom and there wasn't enough light to see very well.

I went back to sleep and woke up at 4a and went to check on them. They were on top of the covers making out and talking to each other. I fired up my laptop and worked on prepping some pictures for the hottie section and posted them.

About 20 minutes later I went and looked in on them and she was riding his cock.

I had arrived just in time to hear S say to him how he touches her in only places that he can.

This hit me like a sledgehammer to the gut, I knew it was the case and I knew at some point I would hear something like this, but I truly was not prepared for that. I watched for a few more minutes, but the more I watched, the more sick I felt in my stomach so I came back out to write this post. As I am, I can her reach orgasm through the wall.

The plan for the morning is to have breakfast here, get cleaned up and packed up, and checked out by 10:30. S wants the 3 of us to go to a coffee shop for about an hour before her and I head off to the airport and fly home. We will be getting home about 8:30p tonight

Before I complete this, a fun thing that S had said yesterday that I forgot to write down is how surprised she was that her pussy wasn't sore with all of its use.
Last edited by jaydub on Mon Oct 14, 2024 9:44 pm, edited 1 time in total.

silky nylons
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Re: The Boyfriend Quest

Unread post by silky nylons » Mon Oct 14, 2024 7:53 am

Beautifully written experience. Thank you jaydub.

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coastalkid
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Re: The Boyfriend Quest

Unread post by coastalkid » Mon Oct 14, 2024 9:54 am

jaydub wrote:
Mon Oct 14, 2024 6:26 am
........
I told her I was just feeling a little overwhelmed with the angst, not being able to sleep with her at night and the sexual things that I was seeing. I enjoyed them immensely, but it was overloading most of my emotional bank. We both talked about how well Dave was doing and the big jumps forward that he was making in his comfort level with me
...........
I could feel myself starting to go downhill as I had been working really hard to keep it together over the course of the day and my lack of sleep for the last couple of nights made it extra hard. Plus the thought of another night by myself on the couch having a hard time sleeping and the discussion of 7 days together coming up all came crashing down on me.

The course of the last couple days were exceptionally hot and fulfilling, but I felt like it was all too much and intense; a result I think of us living together, having the intensity of the sex ramp up, which is a good thing, and the intensity of their love and relationship with each other especially the sleeping part without any break to it had caught up to me.

S came out and I was doing some packing in our bedroom. She could tell that something was up and I told her I just wanted her to enjoy the night and I didn't want to burden her on her last night. She wanted to know what she could do differently about the sleeping situation because I had asked her to help me earlier in the day. I told her not to worry about it and that I was going to get through it. She asks several more times but I insisted that she just have a good evening.
....
I had arrived just in time to hear S say to him how he touches her in only places that he can.

This hit me like a sledgehammer to the gut, I knew it was the case and I knew at some point I would hear something like this, but I truly was not prepared for that. I watched for a few more minutes, but the more I watched, the more sick I felt in my stomach so I came back out to write this post. As I am, I can her reach orgasm through the wall.
I realize you're busy with the aftermath of Hurricane Milton and I'm grateful you didn't suffer major damages, so I don't expect a quick reply.

Your seven day vacation/ordeal sounds like a true learning experience with some tough lessons. Thank you for sharing the good and the bad parts. You've had a lot of "alone time" (even though you've been with S and Dave the whole time) and I'm certain that your brain has been grinding on the things you've seen and heard over those seven days.

I admire your ability to set aside your feelings to facilitate S's experience. It was also good that you shared with S that sleeping alone was causing you anguish. It seemed like S knew you weren't in a good place. Even though you tried your best to not let it show, she knew "something was up". It occurs to me that, like the things you heard and saw can't be unheard or unseen, S has also seen your struggle and suspected your angst. That can't be unheard or unseen either. When you insisted that you would "get through it", and S wanted to think of ways to "do something different", S had to get a sense of helplessness. I imagine she has some mixed emotions from all the things she saw and heard too.

From the way you describe Dave it doesn't sound like he's up to an agenda or an ulterior motive. Your seven day experience was in my opinion a kind of undeclared experiment for you and S, to see how it would go and what the results would be. I get the feeling that seven days was too long. It seemed to me that the initial thrills gave way to angst, a sick feeling in the pit of your stomach and even tears. I know some people will say that's part of whole experience and that's what makes the experience so intense. If it hurts, it hurts and hurting is never a welcomed or pleasant experience. Maybe the seven days was long enough for you to see a potentially difficult routine for yourself and S.

I expect S will be pressing you to divulge your deepest feelings when you're back home. She won't be able to deal with knowing you struggled, offering to find a solution and you declining her offer and insisting that she "just" have a good time. Between that and the things she knows she said to Dave (even the stuff you didn't hear and can only guess about) I'll bet her head is grinding on processing all the different dynamics.

Imagine if it had been two weeks instead of one? Would that have been too much for you?

Take your time in responding, you've got a full plate on your hands.
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Re: The Boyfriend Quest

Unread post by Tap » Mon Oct 14, 2024 11:07 am

coastlkid: I think the 7 day vacation is yet to come, around Christmas time. My understanding is that all three of them have been together for no more than 3 nights that coincided with a business trip for Jay and his wife, S.

I do suspect that Dave has an agenda. I don't think that he is a friend to Jay, but rather, is his competitor. I suspect that he wants to replace Jay. He is starting to dominate Jay. He has already laid down the law on when Jay cannot come inside his own wife. That was an unreasonable demand from Dave, and, was way out of his lane.

Jay accepted Dave's law. I think a better response from Jay would have been to say that Dave does not control how Jay and Jay's wife have sex with each other. If the wife's post-coital condition is then not to Dave's liking, he can regard it as a missed opportunity, and, be alert for a time when husband and wife have not just been with each other.

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Mon Oct 14, 2024 11:26 am

Coastal kid, thank you so much for that amazing, insightful, and incredibly kind message to me. We are all good. We’re on the West Coast. PNW area. Actually I think we were in your region by looking at the location in your profile. Shoot me a DM if you have time, I would love to chat At the airport now getting ready to catch a flight.


Tap thank you for taking the time to weigh in, however, that is completely off base and is the farthest thing from the truth

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coastalkid
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Re: The Boyfriend Quest

Unread post by coastalkid » Mon Oct 14, 2024 1:34 pm

Tap wrote:
Mon Oct 14, 2024 11:07 am
coastlkid: I think the 7 day vacation is yet to come, around Christmas time. My understanding is that all three of them have been together for no more than 3 nights that coincided with a business trip for Jay and his wife, S.

I do suspect that Dave has an agenda. I don't think that he is a friend to Jay, but rather, is his competitor. I suspect that he wants to replace Jay. He is starting to dominate Jay. He has already laid down the law on when Jay cannot come inside his own wife. That was an unreasonable demand from Dave, and, was way out of his lane.

Jay accepted Dave's law. I think a better response from Jay would have been to say that Dave does not control how Jay and Jay's wife have sex with each other. If the wife's post-coital condition is then not to Dave's liking, he can regard it as a missed opportunity, and, be alert for a time when husband and wife have not just been with each other.
I see that I misread that, thanks for setting me straight. If all those things occurred over a three day experience then I don't feel like he's up to a seven day experience unless there is some serious intervention from S. If S is the loving wife I believe her to be then she has some serious thinking to do. She has to know if she chooses to do nothing then nothing will be done to help Drew (I hope I got his name right). She knows Drew finds the idea exciting while also witnessing his intense (I'd say tears are pretty intense) struggle with it. She must feel the pressure of how she needs to deal with the rough spots.

S doesn't know Drew overheard her saying, "You touch me in places that only you can!" S doesn't know the full extent of Drew's angst. Drew doesn't know if S said what she said was out of context and for Dave's benefit or if she was being honest and stating fact. Drew seems determined to "tough it out" but he can't hide his emotions from his wife, she knows him too well. Drew's stoicism and S's NRE seem to be heading towards a hard discussion.

I'm hoping S will see things clearly and make adjustments/compromises/accommodations that will minimize the emotional tension. Women have the power here and it will always be true that with great power comes great responsibility. In general it's been my observation that it takes an exceptionally smart, sensitive woman to make this work.
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Re: The Boyfriend Quest

Unread post by Jujube » Mon Oct 14, 2024 2:23 pm

Drew was the original name jaydub gave to Dave. Nbd. I’d just like to say how lucky you two are to find a guy like Dave. I think his military background contributes to his even-keeled contributory demeanor. I completely understand your major angst about the sleeping arrangements, and I can appreciate Dave’s struggle getting hard, it’s so new and unconventional for both of you. I also find that S telling you that she is going to “take charge” more about developments is very hot! It’s obvious that she’s in love with him, but I don’t think it’s a threat at all. She’s joined with you at the hip! It’ll get easier, I promise. I would love to hear about what she tells you about him and her when she comes to you after he “rails” her. I don’t think I’ve ever read about 3 such good natured and sensitive people in a triangular relationship!

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Re: The Boyfriend Quest

Unread post by jaydub » Mon Oct 14, 2024 5:22 pm

Early in on a post, I inverted our 2 names.
So a reset for everyone:
S is my incredible wife
Dave is the amazing boyfriend
I am Jay the husband

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Re: The Boyfriend Quest

Unread post by Tap » Mon Oct 14, 2024 5:48 pm

I thought that I had the number of their meet-ups down pat. I now realize that I am confused, and, I don't know don't know how many meet-up events have occurred, nor, how many days and nights each was. Maybe, some other reader of the thread, or, even Jaydub, himself, will be kind enough to sort it for us.

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Re: The Boyfriend Quest

Unread post by Cuckcuckgoose1 » Mon Oct 14, 2024 8:56 pm

Yeah I'm confused as well. I thought we were through Saturday night but your most recent post states it was Friday. Do what happened Saturday and Sunday?

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jaydub
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Re: The Boyfriend Quest

Unread post by jaydub » Mon Oct 14, 2024 9:21 pm

Sorry for all the confusion, our first meet up in August was Friday Saturday, Sunday and leaving Monday morning

I just fixed the last post that said Friday, it should’ve said Sunday. I’m writing these posts at three in the morning with my angst up and no sleep so apologies for the errors :-)

S and i just arrived home from this long weekend getaway. We arrived and met him on Thursday and we departed noon time today (monday)

The most current post takes us through 5:30 AM Monday morning about 7 hours before we departed the house. Quite a bit of things transpired today for us to work through, all is well. Hoping to have an update mid week for everyone.

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