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.
