Jill's first time with another man.

[Funcpl500]

This is a true story about the first time my wife Jill enjoyed another man.

My wife Jill and I had been married for 15 years when we first decided to open our marriage. It started innocently enough. I was her first, and she was very sexually inexperienced. One night, we were lying in bed, and we started talking about her first true boyfriend. She mentioned that they did try to have sex one night, but he struggled to get his cock inside of her and could not hold back his orgasm and released in the condom before getting in. She had already shared this with me years before, but she went into more detail about that evening.

I asked her how big he was, and she said that he was bigger than me, which was most likely the reason they couldn't get him in her the first time they tried. I asked her how much bigger it was, and she said several inches. I’m average-sized at 6 inches and a bit thick. I have smaller balls, and she said his ball sack was really big. She said that when she gave him head, her jaw would hurt after. He would cum in her mouth, and she would not swallow but spit it out. Apparently, he was a big cummer, and she would have to have a towel ready, as it would spill out.

Over several months, we would role-play that he did get his big cock in her and that he would release all of that cum inside of her. She had never had a real orgasm until we role-played. Our sex was amazing, and she found out that she was a squirter one night. Our dirty talk was so crazy that when she really had a true orgasm for her first time, she squirted. I pulled out and started to rub her clit, and she shot fluid at least two feet across the bed. We had to start lining the bed with towels after that.

This role-playing went on for about 6-7 months before we had a deep conversation about trying it for real. At that time, I had to go to a business event in San Diego, and we decided that she would come along, and it would be the perfect time for her first partner. Craigslist was still available as a way to find a partner, and we created and posted an ad. We had several dozen responses and selected one. He was a 27-year-old single male, fit, and was open to sharing his most recent STD test. He sent several pictures of himself, both nicely dressed and with his clothes off. He was definitely fit and nicely hung at around 7 inches. We did not want to pick someone much larger than me for her first time.

We also shared pictures of her in a sexy outfit. She was not comfortable sending nude pictures or anything with her face in a picture. My wife is 5’ 7” tall and, at the time, was 120 lbs. with a small, perky chest and fit. After having 3 children, she got back in the gym and in shape.

When the time came to head to San Diego, we confirmed a date and time and a place to meet her partner. We selected a dance bar near downtown and walkable to our hotel. When the day arrived for the meetup, she shaved her pussy and left a little landing strip of hair. I was in meetings most of the day, so she had all day to prep. She also went out to purchase condoms. She was not on birth control, and I had a vasectomy several years before. It was a good time for her to play, as she was several days away from her period and no longer ovulating. At 39, she was still very able to get pregnant.
Well, the time arrived for us to go to the bar, and we walked 5 blocks to the venue. We were to meet him at 10:00, and we arrived at 9:30. We picked a nice booth near the dance floor. She loves to dance, and it is a great way for her to flirt. We both sat on the same side of the booth, and I started to rub her smooth legs. She looked so radiant in a nice, slim, and short black dress that nicely showed her body in a classy way. Under the dress, she had on a lace bra with a matching thong. I did sneak my hand up her dress and rubbed my fingers across her pussy lips, and she was dripping wet.

We ordered a round of drinks, and we both downed them in about 5 minutes. We ordered a second round we nursed those a bit longer. As 10:00 approached, we nervously started looking towards the entry to the bar, looking for the guy. We kept looking at 10:00, 10:15, and when 10:30 hit, we knew we had been ghosted. Yep, folks, her first time with all of the prep, excitement, and anticipation, the guy did not show. We both were devastated.

We still had other responses from the original ad, and we sent notes to several of the men while we sat in the booth. One of them responded right away that he could meet up with us. This was not an ideal situation, as we did not have an STD test or a lot of information about him. We were both now 3 or 4 drinks into the evening and not feeling much pain. We decided to agree to meet with him.

He was 29, 6 feet tall, very fit with an 8-inch thick cock. He was a sales rep for a software company. The one thing about him that she was kind of excited about was that he was a black man with experience being a partner for several couples.

With 4 drinks now in us and it being 11:30 or so, the dance floor was in full swing, and she was out dancing with several other women. I’m not a big dancer, but I did go out for a few songs. We were having fun and did not even notice that Ray had arrived at the bar and was looking for us. I weaved my way to the bar and introduced myself, and pointed out Jill, who was still on the dance floor. Ray was very nicely dressed, more in professional attire and not in clubbing clothes, and, fully clothed, looked to be as advertised. I took him over to our booth to sit down.

After another dance, Jill came back to the booth and sat down next to Ray. He introduced himself and kissed her on her cheek. They started talking about San Diego and how he likes living in the city. With her being a bit drunk, she was not shy at all. She asked him if he wanted to dance, and they headed out onto the packed dance floor. They danced for a good 30 minutes and came back to the table, where I had a new round of drinks ready for us. Ray excused himself to the bathroom, and I asked Jill what she thought. She was a bit sweaty from dancing and red in the face. She said it was not from dancing and that he slid his hand up her dress when they were dancing and fingered her. She was totally ready to head to the hotel room and play with him.

When he came back from the bathroom, we discussed heading to the hotel. We gave him our room number and asked him to meet us there in 30 minutes. This gave her time to get ready before he arrived. When we got back to the room, she pulled up her dress and spread her legs for me. Her pussy was so puffed up and wet and ready. I pulled out my cock and fucked her for 5 minutes to open her up and get her ready. I did not cum in her and held it back.

She cleaned up a bit, fixed her hair, and makeup. We talked a bit to make sure that we both really wanted this and that we had our ground rules set. No sex without a condom, no facial or swallowing, and she wanted to be able to kiss him. She wanted him to cum on her belly so she could watch it.
When he knocked on the door, our hearts literally skipped a beat. I could not believe this was really about to happen. She was nervous to the point of slightly shaking. We let him in the room, and he came right in and hugged Jill. Started telling her how wonderful she looked and that he was happy that she selected him. We did not tell him that he was our backup choice. They sat on the side of the bed next to each other and held hands. He asked her what she liked and what she wanted to do to him and what she wanted him to do to her. She basically said that this was her first time with anyone but her husband and that she was looking for new things. She did repeat our ground rules, and he was good with them.

Once that discussion was completed, they started to kiss each other, and his hands started to massage her back and her chest. This went on for 5 minutes or so, and he stood up and had her stand. They started kissing again, and he was feeling her ass and was running his hands up her dress. She was also feeling his ass and slid her hand in between herself and him, and was rubbing up and down his thigh. At one point, she felt his bulge and started to rub his cock through his pants. He flipped off his shoes and sat down on the bed, and removed his socks. He then stood back up again and faced Jill. He asked her to undo his pants and slide them down. She slid them down, and he stepped out of them. His cock was pushing against his boxers and to the side and looked fully erect. She grabbed a hold of his cock through the boxers and just looked down at it.

He then told her to get down on her knees and to pull down his boxers. She did so, and his cock literally sprang out of the boxers. He just stared at it for a few seconds and grabbed a hold of it and started to kiss the side of his cock. It was big. She licked the shaft and the head. The head was leaking pre-cum. She licked it up and started to suck his cock. She did this for a couple of minutes, and he had her stand back up. At this point, his boxers were still around his knees, and he took his shirt off. She was still fully clothed, and he brought her close to him and started to kiss her. His cock was rubbing on the outside of her dress.

He started to undo her dress, and it fell to the floor. He then slid off his boxers and asked her to sit on the side of the bed. He kneeled in front of her and started to kiss and lick her feet and up her legs to her thighs. He did this for a couple of minutes and then moved back up to kiss her and lean in so his cock was rubbing on her inner thigh. He took off her bra and started to suck on her tits and nipples. She started to get really worked up at this point and reached down and started rubbing his cock against her leg. His pre-cum was coating the side of her leg. I could see the film it was leaving. She started to get more aggressive and moved his cock up and rubbed it on either side of her pussy. She started to tell him how great he felt and how hard his cock was.

At this point, he had her lie down on the bed, and he spread her legs and started licking down from her tits to her pussy. He took his time and was licking all around the sides of her pussy. He began to push her up a bit and started to rim her ass with his tongue. This is something that I never did, and she literally started to buck and shake due to how amazing it felt. She was so wet that fluid was leaking from her pussy, and he started to lick it up and parted her lips, and dug right in. She was moaning and grinding against his tongue.

After several minutes of going down on her, he climbed up so his body was on top of hers, and he started to kiss her. His cock was off to the left of her pussy, and she grabbed it and started to rub it on her side. He began to finger her with one and then two fingers. He also put a finger in her ass. Two in her pussy and one in her ass, and she went bonkers.

When he was done, he leaned up on his elbows a bit, and she took his cock and started to rub it on the outside of her thong and up and down her pussy. She did this for a couple of minutes and then had him roll on his back, and she started to give him a BJ. This was the first time I really got a look at his cock and balls. He was fully shaved and totally as advertised. Had at least 8 inches, a big head, and a nice, tight ball sack with balls that were not overly large.

After sucking him for a few minutes, she lay down on top of him and started to roll her hips side to side, and I noticed that his cock was between her legs and poking up through her ass cheeks. She was moving the shaft around on her pussy. I got a bit concerned at the moment that they were not going to use a condom, so I moved towards her and said, “Don’t forget the condom,” and she said, “I’m just teasing him a bit”.

When she finished teasing him, she rolled over on her back, and he reached over to the nightstand and opened a condom, and put it on. She spread her legs wide, and her pussy was wide open. He started rubbing the head of his cock up and down her slit, and she was saying “oh my god, oh my god, oh my god” over and over again. He then slowly pushed the head of his cock into Jill and started to push in and in about a minute he was balls deep in her. I thought wow, she took all of it like a champ. He was now slowly pumping back and forth, and she put her hands up on his chest to control his depth, as now it was a bit uncomfortable for her. No cock has ever been that deep in her. He fucker her in missionary for a couple of minutes and then raised her legs up on his shoulders and pushed in even deeper. This did hurt her a bit, and she asked him not to go so deep.

After a couple of minutes, he pulled out, and I asked him if he wanted to see her squirt. He did, and I told him to start to rub her clit slowly and then build up faster. In a couple of minutes, she squirted, and it shot all over his waistline. He started to laugh a bit and said that it was amazing. He had never seen someone squirt that far. We now had a massive wet spot on the bed, as we forgot to get a towel.

Over the next hour, he fucked her in nearly every position, and we found out that she loved doggie the best. She had two more orgasms and, when it was time for him to cum, they were in missionary and he pulled out, pulled off the condom, and shot his cum on her belly and in between her tits. At this point, he then moved up to her head and told her to clean off his cock with her mouth. I nearly lost it at that point. She sucked and cleaned his cock.
When they were done, I got a towel and cleaned the cum off of her. They cuddled and talked for about 10 minutes, and she was ready for him to leave. He put his clothes on, gave her a big hug, and asked if he could come back tomorrow and do it again. Sadly, we had a flight home the next day.
After he left the room, I pulled down my pants and fucked Jill for about 2-3 minutes before I blew my load in her. It was our first reclaim sex. For the next 3 days after fucking Ray, she kept telling me that she could smell his cologne on her. This seemed to bother her a bit. She did have “buyer's remorse” and we talked about it a lot on and off for the next couple of weeks. It was nearly a year later before she wanted to try it again.

She’s now 55, and we no longer play with other men. In the years that followed her first experience, she played with 22 men, and several of them were long-term partners who are still, to this day, social friends of ours.

[Funcpl500]

Here are a few pictures to go with the story. Put them in the hotties forum. I found these in my archives of that night. I will post more when I get a chance.

viewtopic.php?f=9&t=77057

[silky nylons]

That’s a beautiful write up of your first time! It was awesome! Thank you for sharing. How old was Jill when this happened? She is a very beautiful woman y the pictures in the Hotties section. More please.

[Funcpl500]

She was 39.

[Fearlesspain]

I love the story! I had the pictures up side-by-side while I read for reference!

I am curious how you went from none in the first year to 22 men over the years and then back to being monogamous again.

I'd love more details and more stories if you're open to sharing. Of course I'd like more photos too if you can find them!

[Vin231]

What a wonderful story. Love all the details. Jill is such a sexy hot wife. I am glad the first time went so well. I am sure she looked amazing enjoying that BBC. That pics of her are so HOT. Like the others I would also enjoy hearing about the others especially the long term lovers and your role in the fun.

[Funcpl500]

Hi- I will get a few more from the night. My role in our hotwife relationship was to help find partners, be there with her to watch, assist with towels, water, and other support functions. She never played solo, as this is what we did together. Was just as much for me as her as well. After care was big with her. We always had reclaim sex.

She stopped being a Hotwife as it was just too taxing on her mentally. It was not just about the big dicks and orgasms. Emotionally she just no longer wanted to deal with the random men.

They made her feel used and she did not want to share her body with them. That’s why in the final years of us doing this, she had 2 regular partners. Both ended up getting steady girlfriends who did not want them playing with Jill. So, instead of looking for a new regular partner, which is really hard to find a person that really clicks with a couple, we just stopped.

I still wish we did it. But her heath is more important than what I would get out of it. Just lucky that we had the experience.

[Fearlesspain]

Thanks for the clarity. I can imagine how difficult that could be on a woman. I love that you guys had the communication ability to work through it all and find what was best for both of you. I love happy endings!

[SoCalOHWFan]

Great story. It sounds like you have a special relationship and a lot of great memories. Thanks for sharing.

[54321]

I still wish we did it. But her heath is more important than what I would get out of it. Just lucky that we had the experience.

And you have some amazing memories!
What a shame you weren't able to find another respectful, long term partner. Internet, ads and swing clubs probably supply plenty of the other kind.

Maybe she might meet someone organically. She is very beautiful and probably has scores of admirers.

Anyway, if you have time, please share more stories and pix of your gorgeous, beautiful hotwife. You must be very proud of her.

54321

[Jackl]

Was there anyone who blew her mind in bed or they were all fun partners?

[Jackl]

Was there anyone who blew her mind in bed or they were all fun partners?

[Funcpl500]

Well, she definitely had a few that blew her mind. I think it was her 4th partner that she ended up playing with at least 4-5 times. He was actually the first guy who gave her a cream pie. There were several other guys that she played with multiple times who really took the time to understand her body and how they could make her cum and squirt.

[Jackl]

What was it about the black men that she preferred? Did you have a lover you enjoyed watching her with more?

[Funcpl500]

What was it about the black men that she preferred? Did you have a lover you enjoyed watching her with more?

As many other people have commented, it was the taboo of the whole black/white situation that really turned us on. One of her long term partners really knew how to get her body going and squirting. He also really knew how to fuck her slow the hard. He was a big cummer as well and it was always amazing watching it leak out of her when they were done.

[DoctorLuv]

Great story & pics. Thanks for sharing

[The Owl]

She stopped being a Hotwife as it was just too taxing on her mentally. It was not just about the big dicks and orgasms. Emotionally she just no longer wanted to deal with the random men.

They made her feel used and she did not want to share her body with them. That’s why in the final years of us doing this, she had 2 regular partners. Both ended up getting steady girlfriends who did not want them playing with Jill. So, instead of looking for a new regular partner, which is really hard to find a person that really clicks with a couple, we just stopped.

I asked a question in the Hotties pictures thread. You have already answered it. Thank you.

[venus-can99]

Do you think if Jill can find another man (BBC?) who is more into her and in for long-term relationship she may start again?

[Funcpl500]

Do you think if Jill can find another man (BBC?) who is more into her and in for long-term relationship she may start again?

We have actually discussed it. The issue is finding the partner. We had to go through a lot of dates to find the two men that she really clicked with. She just does not want to go through that process again and have all of the mental ups and downs and bad lays where she shared herself with someone she just does not care about. Too mentally taxing on her. Sadly, the 10 years or so that we played really did some mental damage to her where she still regrets some of our decisions.

[venus-can99]

Sorry to hear about her troubles. If her heart isn't in it then it is certainly not worth engaging in it. Hope she has recovered from the worst of the experiences and focuses on the positives from her 10 years of playing. I am sure you offer her full support.