📚 simon-simone Part 2 of 1
Part 2
simon-simone-pt-02
GAY SEX STORIES

Simon-Simone

Simon-Simone

by Smoothandlovely
19 min read
4.1 (2000 views)
gay male sexoral sexanal sexcrossdressingincest
Loading audio...

Simon/Simone--Part 2

As the boys went shopping, I lounged around the pool, resting and thinking about meal preparation. It is not very difficult to plan a BBQ during the summer and dealing with recent college graduates and young professionals makes entertaining easy if there is plenty of cold beer. I oversimplify but still it is a reasonable assessment of the situation.

I stripped off my bikini bottoms and swam naked for a while, then used suntan lotion to provide sun protection and keep my skin slick. It was a lovely day, and I enjoyed the peace and quiet since it gave me time to reflect on the night that I spent with Thomas. I had never slept with him before, so it was a new experience, as was having sex with him in the pool yesterday. There was a lot to unpack but overall, everything with him was positive, as was my brother's reaction to it all.

I rolled onto my stomach after a while and shortly thereafter, I heard Vincent and Thomas return from shopping, sweeping through the house like Huns and making enough noise for a dozen people as they proceeded to put things away in the kitchen. I heard the patio door open, and Vincent came by with a cold beer for me, sitting in the chair beside me as he rubbed my butt with his cold hand. "Oh, what a nice warm butt," he said softly. "The roundness excites me, and I certainly wouldn't mind seeing if it is as soft and tender as I remember." He ran his finger up and down the crack, stopping several times to place his index finger on the edge of my rosebud, massaging gently.

"Vincent, you know this is an invasion of my privacy and if you don't stop in the next 10 minutes I will scream," I said without moving. "Where is your partner in crime?"

"I believe that he went to make himself presentable or perhaps just to have a quick wank after seeing you lying here naked," he replied. "He walks around with a hardon most of the day and seeing you stretched out and slick with suntan lotion is just enough to send him into a frenzy.

"By the way, was he well behaved last night? He is a friend, but I don't want him forcing himself on you so if this isn't what you want, tell me."

"You're sweet and I appreciate your concern, but Thomas is a nice guy. I never imagined that we would have a connection but there seems to be some chemistry between us and so far everything is fine," I said quietly.

"Just to be clear, in the future will I have to make an appointment if I want some time alone with you? I have certain needs too and as much as I hate to interfere with your sexual activities, I don't want to be left to jerk off by myself. Sorry, if that sounded rude."

"My God, one minute you're a sweet caring brother and the next you're like a buck in rutting season focusing on getting laid." Raising myself on my elbows to look at my brother, I said softly, "Vincent, when have I ever said no to you in all these years? Do you honestly think that I would let a caring, kind and loving gentleman like Thomas deprive you of your sexual satisfaction? Impossible even to consider, isn't it?" I said as I rested my head on the cushion.

"You don't think that I have feelings, do you? I'm hurt Simon," Vincent responded with a smile, then rubbed my butt before slapping it and left to go inside."

Lying in the warm sun, savoring the aroma of the coconut from the tanning lotion, drinking some beer and talking to my brother after he massaged my anus, gave me a semi-erection and made other parts of my body ache for some attention. I picked up my phone and sent a text to my brother: "This is what you do? You rub and slap my ass, talk about sex, ply me with alcohol and then walk away leaving me in heat? If you don't do something about this pretty damn quick, I may have a headache the next time you come knocking on my door. Kisses."

A minute later came the reply: "I was just thinking about coming down for a swim. Would you want to join me?"

Answer: "Yes, nice of you to ask, now get down here."

As Vincent came out to the pool he commented, "This must be the first time that you requested my company instead of it being the other way around. So, you really do enjoy the special attention you get from me regardless of what you may have said over the years. I'm flattered."

I got up from the lounge chair, and looked back over my shoulder while walking to the pool, accentuating the movement of my butt. "I believe that you said something about a swim, right?" I jumped into the water and felt the chill of the water engulf my warm body while I swam to the shallow end near the steps to wait. Looking back at Vincent I saw his erection pointing to the sky and was pleased that he still got as excited about swimming with me now as he did when we were younger. Our special relationship began as something convenient for him, the benefit of having a younger brother who turned out to be gay and who appreciated being able to hone his skill at pleasing other males, but it matured into something different, more akin to a genuine affection with benefits.

My thoughts were broken by the splash of Vincent jumping into the pool and swimming underwater to where I stood. I felt his hands on my legs as they moved slowly from my knees to my pelvis and around to grasp the cheeks of my butt to pull me closer to him, my penis coming to rest on his face before he rubbed it across his lips and nose. When his head broke the surface I stared at him for a second in disbelief before commenting, "Wow, that was a first. Is there something that you want to tell me, brother?"

"Don't be silly, Simon. I used your hips to pull myself to the surface. What did you think I did?" he replied with a grin.

"Nothing, I guess, you were just using me as always, but I liked it," I joked as he spun me around and held me tight, pushing his hard cock against my spine before letting it inch downward along the crack of my butt and stop when it slipped between my legs. He moved his hands to my chest and took my nipples between his thumb and forefingers to gently twist them until I moaned in delight. "You always know how to excite me, don't you?"

📖 Related Gay Sex Stories Magazines

Explore premium magazines in this category

View All →

"Of course, just like you do me," he said while sliding his hands down to my hips and using his thumbs to separate my butt cheeks.

I positioned myself to kneel on the pool steps and spread my legs while Vincent separated my butt cheeks and placed his stiff dick against my anus causing me to moan softly. Slowly he pushed forward and the pressure of this movement made my sphincter expand to allow the passage of his hard cock into my colon. I clenched my fists and groaned as my body accepted this foreign object slowly making its way into me. The initial pain gave way to pleasure, and I closed my eyes to focus my attention on the sensations that I was feeling. Once Vincent had the full length of his dick into me, he held still and moved his hands to my chest and began to massage my nipples heightening the feelings running through my body. I was beginning to whimper as my body reacted to the assault on the lower regions, the stretching of my sphincter, the pressure on my prostate, and the force of the penetration. My nipples were tingling as Vincent alternately squeezed and released pressure allowing the blood to flow back into the tissue. I was shaking from the conflicting sensations and then he started to thrust in and out of my anus while holding me in place by my nipples.

"God, Vincent don't stop! I feel like I am going to explode," I cried as I experienced the most intense orgasm of my life. I steadied myself on the steps in the water and told Vincent to hold me tight. He pulled me close and screamed as he began to pulse hot semen into my colon for what seemed like minutes. I was shaking from the aftereffects of my orgasm and Vincent's penis was starting to shrink and slip out of my sphincter's grip while my breathing slowly returned to normal.

I turned around to face him and he gave me a warm hug and a kiss on my neck. "That was intense," he said. "I don't remember ever having an orgasm like that."

"That makes two of us," I replied. "I'm drained."

"That was an amazing scene to observe," said Thomas from one of the lounge chairs where he sat watching us. "If it was good for me, I imagine that it was ten times better for you."

"I didn't realize that we had an audience, I feel like a porn star," replied Vincent with a forced smile.

"I didn't notice you arrive," I said. "Were you there long?"

"Not very," Thomas replied. "I didn't want to interrupt the fucking so I thought I would make myself comfortable and watch. I'm sorry if that upsets you."

"It would have been nice to know, that's all," I said frostily as I got out of the pool and grabbed a towel. "I'm going to shower and will be back in a little while to talk about dinner." As I walked away I could feel semen running down my leg, but I didn't want to make a big deal out of it, so I ignored it and kept walking. I heard Vincent and Thomas talking quietly but I could not discern what was being said although it did not seem to be the usual good-natured conversation.

After showering I just put on shorts and a polo shirt for leisurely lounging around the pool and went to the kitchen for a glass of wine. When Vincent saw me through the window he walked in to talk. "Are you okay?" he said with an air of concern in his voice.

"Yeah, why do you ask?" I replied.

"It seemed that you left rather abruptly before and I want to make sure that nothing is bothering you," he said. "Let me rephrase that; I want to see if you want to talk about it. I understand that you're upset and I don't blame you."

I took a deep breath and blurted it out. "I don't mind what we do, in fact I enjoy being with you, and you know that. I had a nice afternoon in the pool yesterday with you and Thomas, and I enjoyed sleeping with him, but it's something else again when someone doesn't respect my privacy, our privacy, and stares at us having sex for their own amusement. I think that that crossed a line and was rude."

"Simon, I get it and when you went inside I told him that he behaved like a juvenile. I think that he understands it now although I am not 100% sure. These little things have a habit of spiraling out of control if people overreact so please try not to make too much of it and let the matter die a death on its own. We can't undo what happened, but we can control most of what occurs from here on out."

I thought for a moment, took a sip of my wine and replied, "You're right. We can't put the genie back in the bottle so hopefully Thomas will forget about it if we, I, don't stir the pot.

"But quite candidly, I am not sure how to react if he wants to sleep with me again. Do I pretend that this never happened and welcome him into my bed? And if I don't, will he get upset at this rejection and react accordingly? What do I do Vincent?"

"Simon, the next move is his so let's see what he does. At the very least I believe that he should apologize to you and then you can see how you feel. Maybe he won't push for sex right away but if he does and you don't feel inclined, tell him you're having your period."

I sighed and laughed, "You're an idiot." I hugged him and kissed him on the lips. "Thanks."

🔓

Unlock Premium Content

Join thousands of readers enjoying unlimited access to our complete collection.

Get Premium Access

🛍️ Featured Products

Premium apparel and accessories

Shop All →

As the afternoon progressed, several of Vincent's friends came by to hang out, use the pool and join us for the BBQ. They brought beer, wine, and snacks, and some of the more mature had managed to conjure up potato salad, mediterranean salad and olives to go with the ribs and chicken that Vincent planned. It was developing into quite the feast with a lively crowd, but then again it's not my home so I could theoretically leave like any other guest rather than clean up or help him entertain. As the main meal finished, I made the rounds picking up the trash not put in the bins, making sure that nothing wound up in the pool, and helping where needed. Quite a few people went into the pool and a couple of the women had their tops off but that's the norm for pool parties involving 20- and 30-year-olds. The guys liked to roughhouse but it wasn't like spring break, and most were more concerned with ogling the topless women than fighting with each other, a sure sign of maturity.

Vincent came around to see me and asked if Thomas said anything to me. I told him that I had not seen him separately all afternoon. Vincent said that he must be embarrassed since Thomas told him that he felt uncomfortable after what happened. Vincent told him to apologize and move on but clearly Thomas might need some coaxing. I got the message and told him not to worry about it.

I put on tiny black bikini bottoms and flopped around the pool like everyone else. The women were very friendly and almost treated me like one of their own, and the guys looked at me like another topless female with an occasional pat on the butt as recognition. It was good fun, and I enjoyed the attention I received with my brother keeping an eye on me just to make sure things didn't get out of hand.

When I saw Thomas was by himself at one point, I swam over to speak with him. "Hi Thomas," I said. "I'm curious. Are you avoiding me? I haven't seen you since this morning and you haven't said a word to me even in passing."

"I don't know what to say, Simon. I did something stupid and now I don't know how to make up for it. Am I avoiding you? Yes, because I don't know what else to do."

"People make mistakes and sometimes they do things that are inconsiderate," I replied. "You can't hide from it forever. The best thing to do in my opinion is face it and simply acknowledge that a mistake was made, say you're sorry and promise not to repeat the mistake.

"I like you Thomas, and that's why what happened this morning upset me so much. I expected more from you. You, better than anyone else, know the relationship that I have with Vincent. You've seen it when the three of us were together so what you saw earlier should not come as a surprise. But I have a right to privacy and I do not appreciate being spied upon. I would be just as angry with Vincent if he were to sit and watch you and I having sex uninvited. This is common courtesy."

"Simon, you're right and I was wrong," he said. "I should have gone back inside when I saw what was happening and given you the privacy that you deserve. But I also think that seeing you made me jealous of Vincent and I didn't know how to deal with it. It's silly and I should have known better."

The last part of what he said caught me off guard. I had never considered the complex emotions that may exist when people form a relationship among friends and family. Thomas brought everything to the forefront by acknowledging simple jealousy. If Vincent were not my brother Thomas may have been jealous of the other man, but the choice would be easier; 'either him or me' he would say, and there would be a clear resolution to a problem when the choice was made. But there is no 'either him or me' now because I could not abandon my family and he knew it. Thomas is faced with a unique 'live with it or move on' scenario that is a lose/lose option for him.

"Thomas, it's not that straightforward of an issue and I am just realizing it now," I replied. "It's not silly and this is not something that you should have known better about, unless you are talking about simply getting involved with me.

"Vincent and I are very 'close', and you can interpret that any way you like, and if I am candid I would have to say that that aspect of our lives is not about to change in the foreseeable future. He is also your best friend, and I don't want to see your friendship fall apart because of me. I cannot abandon Vincent but I can say that as much as I like you, I don't see a future in any relationship that we may have because of what you know about Vincent and me. What you did this morning was a mistake, but it highlighted a much bigger problem that must be addressed, and I am the only one who can address it. We had some fun one night and now we must move on with our lives. You will find someone else and so will I, you and Vincent should remain best friends and there will be harmony within my family as well. If something develops between us in the future, we can deal with it at that time. Now, let's enjoy the afternoon watching the lovely ladies frolicking in the pool and stay as friends."

Thomas seemed dejected but I could tell that he agreed with my assessment of the situation. He cared for Vincent and realized that having a reliable friend was worth much more than casual sex with someone that may not develop into anything else because of the danger to the friendship. "Thanks for the chat, Simon and I owe you a beer for being rude to you earlier," he said as he started floating away.

"Okay, and I'll hold you to it," I replied.

When I caught up with Vincent a little while later, he said that he saw me talking to Thomas and asked if he apologized. I told him that we discussed what happened and he did apologize so all is well at the moment. I asked that he not bring it up anymore and suggested that we forget about it so we can move on and avoid tension. He agreed but I was unconvinced that he would be comfortable with that decision.

As the day wound down and people slowly left for home, Vincent and I cleaned up and said our goodbyes to everyone before going inside for the night. We were finally alone, and the house seemed uncharacteristically quiet, but the silence was not unwelcome. I told Vincent that I was going to take a shower and would return for a drink if he didn't mind company. He agreed without hesitation and said he was going to shower as well and would meet me in the den.

After showering I slipped into a short, dark blue satin nightgown, one of my favorites for Simone. It made me feel sexy, looked beautiful, and it seemed a good choice for a quiet drink before bed. I went to the kitchen and got two bourbons and took them to the den which had sliding glass doors facing the pool, where I waited for Vincent to join me. The nighttime temperature was still pleasant and the pool looked beautiful with the underwater lights illuminating it so it was a relaxing atmosphere at the end of a hectic day.

Vincent came down about 15 minutes later than me, stretched out in the lounge chair next to mine and sipped the bourbon while looking out at the pool. We talked about the BBQ and some of the silly antics that took place during the day, eventually agreeing that it was fun having so many people around again. When the conversation trailed off, Vincent asked if the nightgown was new since he didn't remember seeing it on me before. I told him that it wasn't exactly new but it was not very old either. I said that it made me feel pretty and was very comfortable for lounging around in the evening, then asked if he liked it. He grinned and let out a short laugh and replied, "Definitely! You look sexy as hell."

"Thank you, you're sweet," I said. "Vincent, kidding aside, can I ask you a serious question?"

"Of course," he replied without hesitation.

"Well, as you can probably tell, I am quite comfortable as Simone and it is becoming more difficult to switch back to Simon," I continued. "It feels strange to be in my own skin at times and I find myself thinking as Simone and seeing things through her eyes. I find Simon to be almost alien and it is concerning to me. Maybe I am overreacting but I don't know. Vincent, you know me better than anyone else, so how do you feel about this double life? Does any of it bother you and if I asked for your thoughts, what would you say?"

"Simon, you have been my brother all your life and that won't change," he said. "We are family, and with me you can be Simon or Simone and addressed as she, or her, or whoever allows you to be comfortable. I will always love you as you. The question is: what makes you happy? I will stand with you and support you no matter what."

Enjoyed this story?

Rate it and discover more like it

You Might Also Like