Evolving as a cuckold - through the seasons of life

[The Owl]

What a great story - that is kind of funny that the guy with stamina seemed confused about doggy style... I wonder what his backstory was! At least he gave her a good time though!

I may not have written about the M-F scene that Scarlett and I observed very well. Once the woman gave him clear cues about what she desired, he knew exactly what to do. I think he may have been worried about offending her if he would have preemptively whipped around behind her, turned her over and lifted her ass to begin doggie!!!

They looked like two people who had just met downstairs, perhaps on the dance floor. She had invited him up to have sex with her. It looked like he didn't know her before this moment, so he did what he thought she wanted on a first "date" (i.e., missionary position). But she wanted doggie. He may not have known what to think when she began resisting having sex in the missionary position with him. After all, isn't that what she had invited him upstairs to do? But once it became clear that she still wanted sex, but it a different position, he was immediately on his game and responded to her request.

When strangers - male and female - begin making their night moves for the first time, there's a lot of learning that needs to happen for each to get their kink on, as it were.

Anyway, he seemed like a capable, confident, and experienced lover. He just didn't seem ready for her to take the lead in in that way at that moment. I loved how she said, "Thank you" to him as they descended off the bunk. It was a sincere expression of appreciation by her to him. He seemed... well, cocky... that he was able to satisfy her. A true no-strings tryst.

There were other men, women, and couples there that night (and some threesomes). If we would have been on one of the larger mattresses, some interactions with others may have occurred in the sex area. But we were just dipping our toes during the first night. Having sex in the presence of so many others who were also having sex was intensely erotic. The choir of female moans was amazing. There were a LOT of women... and men... having unadulterated and very raw sex. As a voyeuristic cuckold, watching and listening to this action put a huge smile on my face. The only thing that would have been even more arousing would be to have the opportunity to watch Scarlett be taken by a virile Third... or by a couple... or by a Female who knew what she was doing and could take charge while teaching Scarlett - a natural submissive - the ropes with regard to FF eroticism.

But what we did was enough for the first night. It was a lot of FUN and made us feel closer!!! We looked vanilla to others... but we had stepped into the world of sex adventurers!!!

[chris41]

Loving the detailed stories within your longer story Owl! Sending much appreciation to you.

[The Owl]

Scarlett and I enjoyed both internal boundary pushing and external boundary pushing. Internal boundary pushing involved deepening our connection by engaging each other - one-on-one - by increasingly various erotic interactions and role playing.

One evening Scarlett put on a skimpy French mail outfit with a feather duster and a white cap, not unlike a small nurse's cap of yore. She told me to go to the bedroom and to strip and lie on the bed. I followed her command and was on my back with my semi-turgid cock draped to the side.

She opened the bedroom door and looked slightly surprised to see me in the room.

In a strong French accent, Scarlett said, "E suis désolé ["I'm sorry."] I thought the room was empty. My name is Monique. With your permission, I shall clean your room."

She began dusting and cleaning around the bed. When she was close to the bed stand, I reached out and gently wrapped my hand around her wrist and asked, "Monique, do you provide other services to guests staying at the Inn?"

"Oui, Oui... Of course. I am here for you. Service is my duty and pleasure. I desire all who seek shelter here to feel rested when they leave, but also to find comfort and pleasure at the Inn. We have a stag stew simmering on the stove if you feel peckish. The broth is flavored with the... how do you call them in English... the balls of the stag. That broth makes many of our guests feel young and frisky, like a stag in rut. Would you like some stag stew now?"

"No. I want you... I want you now." I slid my other hand up the back of her thigh, and ran it under her very short French maid skirt. I caressed her buttock which was covered by a very thin layer of french lace.

She gasped lightly and said, "Look at you. Your penis looks happy. Have you already tasted my stag soup?"

I pulled her to the bed and we stayed in role. Monique said, "I have limited time and many more rooms to clean. There are many more guests to service. Some are quiet handsome and like it when I spend a lot of time helping them mess up their beds a bit more before I clean the sheets. A few couples who sleep in double beds seem to think their bed is a triple. I always try to make it work for them... both of them."

I started unbuttoning her white blouse. Monique (Scarlett) said in her seductive French accent, "No time for that. Let me remove my panties for you so your cock can enjoy me. I do not have time to dress and undress in every room."

I tried to kiss her but Monique turned her lips away and said, "My apologies. I do not kiss the guests. But I am happy to fuck."

Without missing a beat, she pulled off her lacey panties and allowed me to enter her moist and eager pussy. Monique said, "I may be a bit slippery down there. Another guest already enjoyed my cleaning services this morning."

As I slowly worked my cock in and out of Monique's very familiar pussy, Monique whispered in my ear, "Please be quick about it. I have many more rooms to clean. There is a gentleman with a very large cock who is waiting for me down the hall. I don't want to be late. Do not worry about my orgasm. He will give me all that I need... all that I want."

Then she said, "Would it help you cum quickly if I slip a finger in your ass?" as she nibbled my ear.

I had an intense orgasm and then rolled off her.

Monique sat up, grabbed her panties and duster and said, "I hope you enjoyed your maid service today. Tipping is optional. Now I need to move along and clean the rooms for all the other gentlemen who await me. If you hear any moans from the last room down the hall on the left, don't worry. That's the room that I clean best. The man with the large cock is staying there. I may clean that room for hours. If you need anything, please do not interrupt. I like my privacy when I am in his room."

She left the room, changed back into her normal attire and began playing the guitar in the living room. I put on my robe and joined her.

Scarlett asked in her normal voice - French maid outfit and accent gone, "Did you have a nice nap?"

"Yes, very nice. Thank you."

As she strummed, she began writing some lyrics to go with the tune, "Naughty by nature. Submissive by choice. Erotic submission feels like power, not weaknesss. Get off, get off, get off... please stay on top... until we both get off. I submissively command you... stay on top... until I get off... then I'll get back to my man's loving arms... Waiting for me... waiting in the shadows... watching me getting off with you."

She looked up at the end of her wandering lyrics and winked at me. She finished the song with a chord way over yonder in the Third key, musically letting me know that she fully intended to submit to a handsome Third when he presented. She deeply desired to be naughty, for our mutual pleasure.

Internal boundary pushing... role playing... the erotic power of imagination.

[venus-can99]

Thanks for the post Owl. That was pretty intense role-playing. I am looking forward to hearing more about Scarlett and her submission to a handsome Third and your involvement in it.

[The Owl]

Before and after the visit to the club, I had been posting occasionally on OHW under the "Hotties" section, including a few boudoir photos. I shared our fantasies and progress toward those fantasies.

Out of the blue, a private message arrived in my inbox from a man who presented himself as an experienced Bull. He lived in the same city as the club we had visited. I'll call him Mr. D - by any yardstick he was a Dom - which, as a natural submissive, was Scarlett's favorite type of man. She likes a man who can confidently have his way with a woman. Scarlett doesn't like a rapist or an aggresssor who is driven by anger. But if a man has a strong libido and Scarlett has given him the green light, then she loves to submit to a confident Dom.

I decided to correspond with Mr. D without disclosing to Scarlett. I did not want to get her hopes up, or her erotic passions stirred, if Mr. D did not pass muster with me first.

To be continued...

[The Owl]

Am I writing into an echo chamber? Is there any interest out there to hear how things went with Mr. D?

[Centaure]

I am all eyes open, please continue your story, thank you for the detailed generous share.

[guitarman]

Owl,
Sorry, I meant to respond to your most recent missive. I always enjoy your recounting of your various episodes leading to your evolution as a cuckold. By all means, please continue.

[johnswan]

Hi, would love you to continue with your story.

I think that, at the moment, with the nuisance of the '504 Gateway Time out' message on every post made, you might get a reduced number of comments. But I'm sure there's lots of interest still.

[venus-can99]

Am I writing into an echo chamber? Is there any interest out there to hear how things went with Mr. D?

Soryy Owl - havent been able to make long posts here for a few days. Would love to hear how Scarlett's and your interaction with Mr. D

[PlzFuckMyHotwife]

While I may not comment much, I'm quite interested in your stories! Please continue.

[The Owl]

Mr. D passed muster. Our messages were clear and we each liked what we heard. I informed Scarlett that I had found a Bull for her to enjoy in a hotel room in the same city as the club we had visited. He was open to me watching. He was actually open to much more but all I was ready to do was watch. And that's all Scarlett wanted as well. We set up the date and time for him to join us in an up upscale hotel. Virtually all of the communication with the Bull was with me. But I showed Scarlett his picture. He passed muster with her.

About three days before we were going to travel and check into the hotel room, Scarlett and I were in bed getting ready for a night of sleep. We were both feeling very aroused as we thought about our upcoming trip. To enhance the eroticism of our plans, Scarlett had decided we should not have sex for a full week before meeting the Bull. She wanted to make sure she was feeling very frisky by the time the day arrived. She also liked the idea of torturing me just a little by restricting me from accessing her pussy during the week preceding us moving from fantasy to reality. Specifically, she had told me, "During the week before we go to the hotel to meet the Bull, I'm going to save my pussy for him. I want my pussy to be fresh and eager when I meet him. And I want you to be feeling especially frisky too, so no orgasms for you during that week. Ok?" We both enjoyed the anticipation we were savoring, including the no sex, no orgasm, rule during the week leading up to the tryst with the bull.

While lying in bed before falling asleep, I was completely naked between the sheets. Scarlett was wearing panties but was otherwise naked. She told me that she was keeping her panties on to prevent me from slipping inside her on a whim – a chastity belt of sorts. I was on my back and she was tucked in tightly beside me. While her hand gently caressed my chest, and her leg was draped across mine, she gave me a kiss on the ear and began talking.

"I need to talk and I need you to listen carefully. First, I want you to imagine what you will feel when you watch me having sex with the bull in a few days. Imagine me naked on my back on the hotel bed. Imagine him naked in full contact with me. Imagine him thrusting his pelvis between my legs, pushing his cock inside me. Imagine me enjoying his cock. I want you to imagine me having an orgasm while he fucks me." She. kissed me lightly on the ear again and continued, "Now, if you have any misgivings about acting out our fantasy this weekend, tell me now. We still have time to cancel if you want to keep this a private fantasy rather than acting out the fantasy with the Bull."

She moved her hand from my chest to my now fully erect cock. She smiled, kissed me gently on the lips and said, "Your cock seems to have answered my question. Your erection tells me you want me to go through with this. I want to do this too... for you... for us. Ok, truth be told, I like the idea of having sex with a Bull. It sounds very enjoyable from a purely sexual perspective. As you know, I am happy to let you watch us fuck from a chair next to the bed as long as you are quiet and unobtrusive. I trust you won't whine, whimper, or gnash your teeth beside the bed once he begins fucking me." My cock was still in her hand. It was still fully erect. She was making her point and it didn't seem to be reducing my arousal. Although she didn't talk about my continued arousal, we both understood what it meant, and what she meant by what she was saying. She continued, "You won't know exactly how you are going to feel until you are in the moment - until you see him enter me. No matter how you are feeling when his cock is inside me, please don't disturb him... or me. I'm feeling a little nervous as I think about what we are planning to do. I imagine he may be feeling a little bit nervous too, even if he has done this before with another couple. I want to make sure he is as comfortable as possible so he and I can both enjoy having sex while you watch. Remember, no whining, no whimpering, no teeth gnashing. We will talk about your feelings after he leaves. If you discover you don't like experiencing our fantasy, we don't have to do it again. But if you have misgivings, tell me now or tell me later, but don't tell me in the middle of my tryst with the Bull. And promise me you won't be mad at me for enjoying his cock while you watch."

After she had finished talking, she kissed me and firmly moved her hand up and down my cock three times in a row. She grazed her index finger over the tip of my cock where she discovered a drop of clear lube beginning to form. She covered her finger with the lube and raised it to her lips, using it as an erotic gloss causing her slightly wicked grin to shine slightly in the moonlight coming through the bedroom window. She moved her hand back to my chest and rested her head next to mine. I replied, "I promise. I want to watch you enjoying having sex with the bull." Finally, we drifted off into the land of nod. Scarlett was taking charge of her upcoming experience. The anticipatory excitement was intense for both of us.

[The Owl]

And who would like to hear how things unfolded in the hotel room a few days later?

[mfmfantasy50]

I certainly would like to here how things went in GREAT DETAIL!!!

[hornedhubby]

As the worm turns....

Enjoying your story, Owl. Thanks for sharing.

[Rogueuser1]

I would love to hear how it unfolded - thank you!

[The Owl]

We flew to his city, checked into the hotel, and awaited his arrival. Scarlett's belly was full of butterflies. I was nervous too but tried to keep a steady hand to avoid creating too many butterflies for Scarlett. I did not want either of us to become overwhelmed with anticipatory jitters. Scarlett had brought a black silk robe that she was wearing in the room while waiting to greet him. The robe was tied at the waist. All she was wearing under her robe were a matching bra and panties designed and handmade in France. I had purchased these items for her as a gift – a gift to be worn by her for the first time during her erotic encounter with the Bull. She was dressed for seduction – dressed to undress.

The plan was for Mr. D to start things off with a sensual massage. If the massage went well and Scarlett felt comfortable, then he could move to second base, and beyond. The only rules we had established was that he would wear a condom (for health reasons) and that her ass was off limits. Scarlett’s pussy is petite and wraps tightly around my average-sized cock. She welcomed the idea of her pussy being stretched by the girth of the Bull’s cock as shown in a photo he had sent. His cock was longer than mine and somewhat thicker – but it wasn’t so large that it frightened her. She was confident that her pussy could stretch to accommodate him. Scarlett was in good shape. Her muscles were toned from regular workouts. Her C cup breasts were perky, her stomach was flat, and her legs were strong from running. She oozed that healthy girl-next-door eroticism. Photos of the Bull suggested he was also very fit with well-defined muscles. He was very masculine in his presentation. Consistent with Scarlett’s preferences, he wasn’t too hairy. Everything about his body fit Scarlett’s preferences perfectly. His physique had just the right edge of Dominance to arouse Scarlett.

Much to both of our relief, the Bull arrived on schedule. We were fully aware that some Bulls talk a good line online but flame out when D-day arrives. When he knocked and I opened the hotel room door, I could tell he was slightly nervous too but he hid it well. He had good social skills and made Scarlett and me feel comfortable in his presence almost immediately. He had a ‘take charge’ demeanor - like a quarterback in the huddle calling plays. His take-charge style was exactly what Scarlett desired. At the same time – just like a competent quarterback – he made us feel as if we were on his team and that we would be just fine if we relaxed and let ourselves loosen up on the field. Scarlett knew that I would soon be sent to the sideline and that she and the Bull would be the players on the field - engaged in an ancient contact sport called sex. Their field of play was the bed where they would move as a team, running the plays under the skillful guidance of the Bull.

I was also wearing a robe with silk boxers under it. The Bull was smartly but casually dressed. I poured glasses of wine for each of us, to break the ice and calm our nerves. Mr. D complimented Scarlett, telling her that she was even more attractive that her photos suggested, as he lightly touched her arm. Scarlett thanked him and told him that she found him to be very handsome as well. She giggled as she softly said, "You exceed my expectations." I could tell that the Bull and Scarlett were off to a good start. He exuded just the right amount of dominance to arouse Scarlett, without frightening either of us by being too dominant – too aggressive.

Moments later, the Bull confidently asked Scarlett if she would like to begin with the massage. She replied, "I would love that." Scarlett was already being submissive to the Bull. I instantly felt fully submissive to both of them. I had entered subspace – cuckold subspace – even though almost nothing had happened yet.

Scarlett stood up, untied her robe and handed it to me as she moved toward the bed. I walked to the chair situated in the corner of the room, a couple feet to the side of the bed, near the foot – close enough to see everything, and far enough away to be out of Scarlett’s and the Bull’s way. Scarlett wanted me to quietly watch and to pay attention to my internal experience, the landscape of my feelings as I watched her savoring the Bull. We had agreed I wouldn’t masturbate while watching. She knew that I would get aroused. She was fine with me quietly touching my cock. But she didn’t want me making fast movements or any noises that could distract from her experience with Mr. D. She certainly didn’t want any commentary from me or having to listen to me uttering play by play descriptions of what I was observing.

There's more... care to read it?

[The Owl]

Wearing her bra and panties, Scarlett lay on her stomach while the Bull stripped down to his black boxer shorts. He climbed on the king bed and kneeled beside her, next to her torso. He used some massage oil and began relaxing her with his firm touch - rubbing her back, arms, and legs. She had her eyes closed. Scarlett made a gentle cooing noise as she exhaled, to communicate that she was enjoying the Bull’s massage. He asked her if she would like him to unfasten her bra. She submissively replied, "That would be nice." A few minutes later, he encouraged her to roll onto her back, at which point they worked together to remove her bra completely. He reached behind him and draped the bra on the bedpost – momentarily glancing up at me – as if to communicate that he was close to scoring. The Bull was in charge. Scarlett was submitting to him. At this point, I knew that Scarlett and the Bull had reached the point of no return. My duty to Scarlett was to remain quietly in the chair while the Bull led her further down the path into the erotic jungle.

Scarlett’s nipples are always very sensitive – left even more so than right. During our email exchanges, I had informed the Bull that Scarlett’s left nipple was her erotic Achille’s heel. If he had access to her left nipple, he had all of her. As her bra was removed, I could see that both of her nipples were already aroused - tight to the tip. He continued the massage, running his hands over the front of her body while kneeling beside her. He didn't hesitate to run his hands over her breasts, using his fingers to firmly stimulate each nipple. While he was firmly rubbing her left nipple between his thumb and fingers, she reflexively squeezed her legs together, signaling the frisson of pleasure she was experiencing.

The Bull confidently lifted Scarlett’s left hand from her side and guided it to his boxer shorts. He placed her palm against the cloth that covered his erection. As he lifted his hand from hers and brought both of his hands to her breasts to massage them some more, Scarlett did not draw back. She kept her hand right where he had placed it. My mouth started going dry as I watched her slowly wrap her fingers around his cloth-covered erection. I watched her as her hand sized him up. She slowly moved her fingers up and down the front of his boxers, knowing that she was giving the Bull encouragement, not that he needed any. Her eyes continued to remain closed. I detected even more movement of her hand. Through the cloth of his boxers, she had wrapped her fingers around his cock and had begun slowly moving her hand up and down his length. The movements remained slow and subtle. She didn't appear to be giving him a hand job. Rather, it seemed like she was enjoying the tactile sensation, touching the sizeable cock that would soon be inside her. She seemed pleased and so did he.

As Scarlett toyed with his cock, the Bull looked over at me, made eye-contact, and raised his arm and hand in a way that unequivocally communicated that the massage was over, and that sex was about to begin. Non-verbally – in an apha-ape way, he was letting me know, "She's mine for the taking and I’m going to take her soon… very soon." From my vantage point on the chair, I knew he was right. She was aroused and was waiting for him to make the next move.

[mfmfantasy50]

Mmmmmmmm!!!

[guitarman]

Following this story with great anticipation. Wonderful writing!

[The Owl]

Thanks for the feeback. It's an enjoyable bit of history to tell. I enter subspace when writing about it.

[Rogueuser1]

Love that eye contact he made with you --- hot! can't wait for more!