Simon-Simone

Simon/Simone

My brother Vincent and I had an interesting relationship growing up. He was four years my senior and while serving as my guide to life, seeking out the various pitfalls and suffering the consequences of his actions in doing so to help me learn, he also paved the way for my journey, weakening the resolve of our parents to be too harsh on the younger sibling who may, from time to time, make similar errors. He was helpful in this respect but as so many younger siblings can attest, there is usually a price to pay for such guidance. Dealing with the cost was another life lesson that was given to the junior sibling for free. I learned about the pitfalls of using drugs and how to avoid certain people that would prove to be a bad influence, and also how to sneak out of the house late at night, which parties to avoid and which never to miss. He was the scout and guide for his younger sibling.

After Vincent finished graduate school and received his MBA, he found a well-paying job for a medium-sized firm in the city and rented a nice house with a pool about 30 minutes away. I was in the second year of law school in another nearby city, so we remained close and managed to see each other at least once a month when I would visit him for a long weekend. During these visits, I knew that I could let my hair down and relax, be open and free to be myself with the only expectation on Vincent's part being occasional sex if he was in between girlfriends, something that I had become accustomed to while in college. I was also free to indulge my fetish for crossdressing and occasionally Vincent would even take me to dinner or a club while I wore a dress, a blouse and skirt, or slacks, and heels. As I said, we had an interesting relationship that worked for us.

Vincent had one very close friend, a fellow named Thomas, who was very outgoing with a sense of humor leaning toward double entendre and suggestive comments, but always in a good-natured way. I had known him for many years and when I saw him I enjoyed teasing him about his many female friends and how they were always smiling which stroked his ego. In turn, he usually had some comment about how pretty I looked, and my lack of fashion sense which did not mesh well with my effeminate mannerisms. We were old acquaintances, and I knew that his comments were not malicious so we usually had good fun together although on one occasion we had a serious interaction that brought our relationship to a new level.

I was visiting Vincent when Thomas stopped by for an impromptu weekend get-together since both were victims of recent break-ups and lacked specific plans so they sought consolation with each other. I knew that my brother would look to me for gratification while I was there and this was not unexpected, something I had grown to enjoy over the years as it maintained a strong bond between us.

I was stretched out on a chaise lounge by the pool in tiny yellow bikini bottoms when Thomas came over with two beers and sat on the lounger next to me. "Hey Simon, you looked hot so I thought I would join you and bring something cold to drink," he said with a giggle, and I should note that he emphasized the word 'hot'.

"Aren't you a gentleman, Thomas," I replied in a sultry Southern voice. "How shall I ever repay you for your kindness?"

"Maybe a dance at the ball tonight, Ms. Scarlet?" he replied.

"You're making me blush," I said and laughed before taking a sip of the wonderfully cold beer. "Now, would you be a dear and put some tanning oil on my back so I get a beautiful bronze glow?"

Thomas acknowledged my request and did not waste any time applying the tanning oil that scented the air with the aroma of coconut while allowing him to gently rub my body as I kept my eyes closed and drifted away on daydreams. His touch felt wonderful and soon my body was slick to the touch. He did my arms, neck, and shoulders before advancing down my back to my waist. He then started from my feet to my ankles and up my legs to my buttocks before asking if he could slip the bikini bottoms down to expose my buttocks to access the last bit of untouched skin. I readily agreed and lifted my pelvis off the chaise to make it easier for him and within seconds he had my bottoms down to my ankles.

I will admit that I was getting aroused by his touch and enjoyed the sensation of the warm oil on my skin. Thomas rubbed my butt and then focused on the crack before sliding one hand down to gently massage my anus while the other rubbed my neck and shoulders. Soft moans escaped my lips as I savored the feeling of his fingers circling the little pucker of my asshole, occasionally probing a little deeper until his finger reached its midpoint.

Using one foot against the other, I pushed the bikini bottoms off my legs and spread them to allow Thomas's hand full access to my anus. I could hear the increased sound of his breathing which matched my own, and I began to slowly move my pelvis, aiding the probing action of his fingers. I knew that if I didn't stop soon I would be at the point of no return and that might be embarrassing for both of us, so I softly told him that I was too hot from his wonderful massage and had to jump into the pool to cool off. Thomas laughed and suggested that we continue another time and I readily promised him a raincheck as I smiled and got up from the chaise trying to conceal my semi-erection in the process.

I dove into the pool and enjoyed the cool water against my naked body as I floated around. Vincent came out to join us, bringing more beer to keep the good time flowing and I left them to chat while I did a few laps. Maybe I looked too comfortable or perhaps there was a surge in testosterone but whatever it was, I soon found myself swamped by waves when two naked guys jumped in on either side of me.

Vincent was in a good mood so before long we were passing a beachball around and this turned into aquatic dodgeball and friendly horseplay. At one point, Thomas grabbed me from behind and picked me up in an attempt to hurl me to one side but I managed to wiggle to loosen his grip although he still held me from behind. As I became upright in the water, I felt his stiff penis against my back and I acknowledged what I felt by making a joke, saying, "Is that a pistol in your pocket or are you happy to see me?" while letting out a laugh.

"Certainly no firearms, but I am very happy to see you, Simon," Thomas replied and laughed along.

"We both are," said Vincent a few feet away while stroking his semi-erect dick under the water.

I knew what Vincent wanted and the thought of his cock in my mouth excited me but I was surprised by Thomas. He and I never hooked up or had a thing but we did kid around with sexy jokes and an occasional rub on the butt but nothing more before today. I purposely had not moved away from him and he still held me close as we spoke, the feeling of his stiff dick more pronounced than before. Slowly he loosened his grip and I began to slide down along his body while he pushed his pelvis forward, eventually feeling his stiff dick press against my anus with the head beginning to enter me. I saw that Vincent was aroused by what he was watching and this encouraged me to be more erotic in my actions.

Thomas released his hold on me and brought his hands around to gently squeeze my nipples, before dropping his right hand to my genitals and pulling me farther down onto his erect penis. As Thomas began to stroke my dick, I squirmed and moaned in delight, allowing him to push even deeper into me.

Vincent moved over to the steps leading out of the pool and then sat on the stone coping. He spread his legs exposing an erect penis and leaned back, beckoning me to come take what he was offering. As much as I wanted to have Vincent's cock in my mouth, I was impaled and unable or unwilling to pull free. Upon seeing Vincent, Thomas moved me up and down on his cock several times before withdrawing and allowing me to swim over to him while following close behind. I knelt on the steps leading out of the pool and held Vincent's legs to steady myself. Looking directly into his eyes, I slowly took his stiff dick into my mouth and began to rhythmically move up and down on it.

Becoming more excited, I spread my legs to feel the cool water against my cock and balls and soon felt Thomas's middle finger massaging my anus before he pushed it inside. I moaned with the pleasure of the moment and also in anticipation of what I hoped would follow. I focused on Vincent's cock but managed to free one hand to rub and squeeze a nipple to pleasure myself, ignoring the fact that Thomas had removed his finger from my ass and was positioning himself to replace it with his hard cock. Gently but steadily he pushed his dick into my ass until he was completely inside me and then began pumping methodically and firmly while I worked to time his motions with what I was doing to Vincent.

Vincent came first, filling my mouth with his hot semen, shaking and groaning loudly in the process, while I swallowed feverishly. Thomas was not far behind and experienced an intense orgasm as he gripped my hips, and pushed himself balls deep into my ass, forcefully sending a load of semen into my bowels. As we separated and I allowed myself to slip back into the pool, I massaged my slightly sore anus and wanted to get a cold beer to refresh my mouth.

Vincent rinsed off and got out of the pool saying that he was making a beer run and would be back in a few minutes. Thomas drifted over to hug me and said, "I don't know if it is proper to say thank you at this time but I will admit that it was great for me. I wanted you for a long time even though I never said anything and I'm glad that we had the opportunity," he said.

I looked into his eyes and replied without showing emotion, "You knew that I was momentarily distracted by a conversation with my brother, and you took that opportunity to slip your stiff cock into my ass, fucking me for your pleasure. Now, when you're satisfied, you wonder if you should say thank you. Where are your manners, Thomas?" I replied with a laugh.

Vincent had returned and heard what I said so he chimed in without invitation, "Thomas, I've known you for years and would never have believed that you would do such a thing. Taking advantage of my younger brother in my own home, no less. I'm shocked."

"Vincent, I may be wrong, but wasn't Simon giving you a blowjob? Did you say thank you?" said Thomas.

"Of course not. He's my brother and he owed me for allowing him to use my pool," said Vincent as the two of them burst out laughing.

"Well, someone had better say something nice to me after I have been so viciously attacked," I shouted. "I am the youngest here and I think what happened is akin to abuse."

"Simon, now I understand why Vincent dislikes you and says that you're annoying. You are annoying but thank you anyway," said Thomas before bowing slightly and kissing me on the lips.

"You know you're always welcome, Thomas," I replied. Now, looking at Vincent I continued, "Now that's a gentleman, Vincent. He has manners!"

"Next time I sodomize you, Simon, I promise to say thank you," he responded, still laughing.

We got out of the pool, toweled off, and got comfortable on the lounge chairs. It had been a nice afternoon so far and we were in good spirits. As we started talking about dinner Thomas suggested going out for dinner since it was just the three of us and we could barbeque tomorrow when we might get a few more people to join us. This proposal was greeted favorably, and we agreed to go to a local seafood place that was quite popular and didn't require reservations. Vincent even said he would pay for dinner if Thomas bought drinks at the bar beforehand and I wore something sexy, at which point Thomas's eyes lit up and he readily agreed. They focused their gaze on me, and I felt the blood rush to my face as I realized that I did not appear to have much choice if I wanted a free dinner.

"Vincent, that's not fair," I said. "I would be embarrassed in sexy clothes out in town, particularly with you and Thomas."

"You and I have gone out quite a few times while you were in Simone's persona and it never bothered you before," replied Vincent. "You always look gorgeous and I think Thomas would find you even more irresistible than he did earlier. It can be like a date. No sexy outfit, you stay home and eat cereal while we go stuff ourselves. The choice is yours."

"Vincent, don't embarrass your brother after he has been so nice to us today," said Thomas. "I would enjoy having a date tonight, but I don't want Simon to be self-conscious or feel pressured to do something he does not want to do."

"You say that because you haven't seen him dressed in something sexy as Simone," replied Vincent. "She will take your breath away and if you manage to get lucky afterward, you will never be the same again. But I warn you, she can be a bitch."

Thomas looked at me as I lay naked on the chaise and responded, "Simon, I would enjoy going to dinner with you tonight, and you may even bring your brother as chaperone. I promise to be on my best behavior and hope that you agree."

"Since you put it like that, how could I possibly refuse?" I answered in my best southern drawl. "I will see what I can throw together on short notice but please don't give me looks of disappointment if you are displeased as I am easily hurt."

We stayed by the pool for another hour or so and then I excused myself to shower and see what I could find to wear to dinner. I brought a few things with me and also kept some odds and ends at the house just in case. I was confident that I would have something suitable, but I wanted to look especially good tonight since the boys billed the event as a "date".

As I showered, I ran over the afternoon in my mind, wondering if I was being too casual about having sex with my brother and readily allowing Thomas to sodomize me in the pool. I enjoy the sex but occasionally I wonder if I am not being too easy or readily available since I have become accustomed to satisfying Vincent for many years. I am selective when I am in the school environment, but Vincent always brings out the slut in me and it seems that it rubbed off on Thomas as well. Letting the warm water cascade over my body made me tingle with excitement and soaping my nipples caused me to get an erection but I was determined that masturbation was not an option today so I began thinking about baseball.

Going through my bag and rummaging in the closet, I managed to find a fairly tight white skirt that came up to mid-thigh, a loose-fitting dark blue linen blouse with long puffy sleeves, and natural color flat sandals. Would this be considered sexy? I don't know if I would categorize it that way, but I wouldn't say that I looked like a librarian either so I will leave it to my dinner companions to decide. I put some light gel on my hair, slicked it straight back, and didn't go too heavy on makeup so I had a summer casual look. When I was finished I concluded that I earned a free dinner tonight and was very worthy to be a gentleman's date.

As we entered the bar area of the restaurant, quite a few heads turned our way and there were some knowing smiles but no comments. Being with two fit guys certainly helped the situation and soon we were accepted by the clientele and bartenders alike. Thomas was particularly attentive and even managed to kiss the back of my neck when Vincent went to the men's room so it did feel like a date even though I had no idea how it would end. With Vincent, it was always just sex and so far my relationship with Thomas was platonic with sex only occurring today, but while the kisses on my neck signaled something altogether different, I did not want to read too much into it.

We had a wonderful dinner with lively conversation, quite a few laughs, and even a round of drinks sent over by people we met at the bar. Vincent was exceptionally nice to me, going out of his way to differentiate this evening from the usual congenial time with his younger brother, and Thomas was as focused on me as I imagined he would be with some of his female friends, so I felt special, getting the occasional hug and discrete rub on my butt. I thoroughly enjoyed the evening and was sad when Vincent signaled for the check and we prepared to leave, but it was better to end the night on a high note.

When we got home it was slightly after midnight and Vincent said that he was going to bed as it had been a long day for him and we said our goodnights as well. After Vincent went upstairs, Thomas told me how much he liked the evening and how pretty I looked before leaning over to kiss me on the lips. I did not pull away but moved in closer, put my arms around him, and kissed him back. We separated after about 30 seconds and Thomas said, "That was nice, Simone."

"I liked it, too," I replied, "although it feels a little strange. You have always been my brother's friend and I couldn't imagine you otherwise, until today. I am glad that we had time together and I could be myself with you."

"I want you to be as comfortable with me as I am with whatever persona you wish to present," Thomas said softly. "I have liked you for a long time but never knew how to approach you until I held you in the pool this afternoon. I wanted you and finally began to believe that you had similar feelings when I saw you tonight dressed up for our date, or at least that is what I wanted to be true."

"It was true, Thomas," I confided. "I thought about you as I dressed and hoped that you would find me attractive, at least as attractive with clothes on as I was to you while naked in the pool. When I felt your lips on my neck in the bar I almost started panting and wanted to turn around and kiss you right there but held back." We kissed again, more passionately this time, and I whispered that I would enjoy having him in my bed if he would like to join me.

"I would like that very much," he said.

As we went upstairs and as I got ready for bed, I kept thinking about Vincent and what he would say when he learned that Thomas and I spent the night together. Would he be upset with me for coming between him and his old friend, or would he react poorly because his old friend is making advances to his brother? Either way, it didn't seem that there was a nice way for Thomas and me to begin a relationship that wouldn't somehow jeopardize our family dynamic or their friendship. I found this troubling because deep down, I loved my brother and enjoyed our special bond, something that developed over many years. I also liked Thomas and wanted to take this to whatever conclusion came about so tonight's stage had been set and I promised myself to speak to Vincent in the morning before letting things get out of hand.

I had curled up in bed when I heard a gentle knock on the door. Thomas came in silently and gently laid next to me under the sheet as I turned to face him. He put his arm around me and I kissed him passionately while he pulled my head toward him. I felt powerless in his hands and enjoyed the feeling of helplessness as his body melded with mine. His erect penis pushed against my leg while mine came to rest on his stomach as he kissed my neck. My breathing became harder and more pronounced as his breath became warmer against my neck. I applied pressure to have him roll onto his back and I crawled on top of him, spreading my legs to straddle him while continuing to kiss him with an open mouth. I liked the feeling of his stiff dick between my legs but I also wanted to feel it in my mouth.

Slowly, I inched downward to lick and tease his nipples and continued down his stomach to his abdomen, ultimately reaching the head of his erect cock which I took between my lips. Thomas moaned with pleasure as I took his dick into my hot, wet mouth and began to move up and down on it, forcing it deeper into my throat with each thrust. He became very excited and I tasted the precum that came from his penis as I worked on bringing him closer to his climax, but he kept control and had me stop before he reached orgasm. Thomas pulled me up to look into his eyes before rolling me onto my back and moving down to take my cock into his mouth to give me the same pleasure that he had received. It was such a wonderful feeling to have my penis in his throat while I held his head and gently guided it to push it in until my testicles rested on his chin. He held my penis in his hot mouth without moving for a while and this was such a remarkable sensation that it brought me quickly to orgasm. I held his head against my abdomen while my cock pulsed semen into his mouth and I could feel him swallowing it as fast as it came out. I moaned and held my breath as I savored the moment of sweet release.