Shemale
2008-10-04
Do You Really Know?
My name is Michael and I have been best friends with Trent since high school. Trent has been seeing Tobi for about six months now but even though they are in a serious relationship, she lives with him, she has never tried to ease me out of Trent’s social life. In fact it is the opposite, she is usually the one calling me to invite me to join them in whatever activity they are up for. Almost from the beginning of their relationship I have felt extremely comfortable around her and somewhat attracted to her. She was so unlike the girls I had dated. When the three of us were together it was like just being with the guys hanging out.
Like I said, we hang out a lot and I have a nice little place on some property that gives me just enough privacy that I can get in my hot tub naked if I so choose. I have done so on many an occasion with a few different young women. Trent and I have gotten in the tub together a few times but just to drink beer and occasionally I would set up a television and we would watch football. Well October rolled around and I decided to clean up the hot tub and put in service for the fall and winter as I normally do (I don’t use it during the summer). Trent and I usually open up the season with whomever we are dating at the time. I wasn’t dating anyone so I just invited Trent and Tobi over and they both eagerly accepted. They came over and we had a nice dinner that we all cooked together. It was quite fun being together as we prepared and then ate a modest meal. After eating, we sat down in the living room and talked as we drank a few beers. The sun set and we decided that there was a sufficient chill in the air to make our appointment with the hot tub all the more enjoyable.
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Trent and Tobi used the guest bedroom to change while I went to my room. I quickly changed and went to take the cover off of the tub.
Up until this time I had not seen Tobi in a bathing suit even though we had spent a whole summer together as a group. So I was quite stunned when I came back in the house to get a few drinks and she greeted me. I am glad Trent didn’t see my reaction to the sight before me because I am sure I stared like some uncouth letch. Her breasts were pressing against her bathing suit so hard I thought the seams would rip out. I could even make out the outline of her nipples. I am sure I stared a little too long and when I finally looked at her face she just smiled and asked if she could help with anything. I am glad she looked me in the eye because I didn’t have any way to cover my rapidly growing erection. I told her I was just going to get some drinks and she followed me into the kitchen.
I purposely tried not to look at her because I was afraid I would totally embarrass myself. She couldn’t help but notice how I eyed her breasts so I was already embarrassed but I was trying to minimize the damage. As I was wondering where Trent was he called out from the living room for us to get a move on because he was ready to jump in the tub. I quickly gathered up some drinks and we headed for the patio and the hot tub. There supposedly is a rule that you shouldn’t spend more than fifteen minutes in a hot tub but I have never followed it.
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We were in for a couple of hours and I can’t remember how many beers. As everybody knows if you give a conversation enough time (especially if you add alcohol to the mix), the subject of choice is almost always sex.
I was surprised by the details that were soon part of our discussion. Trent was very open in talking about his previous women. As surprising as this was to me that he was discussing his conquests in front of his current girlfriend I was more surprised by Tobi’s reaction. She seemed to get more and more excited the more Trent shared. She was wriggling around and adjusting her swimsuit as he talked. She even asked him for details. She asked if his ex’s gave as good a blow job as she did to which Trent wisely said no. In fact he stated that she was the best and he was sure he would never experience better if a thousand “people” went down on him. I found it odd that he said “people” rather than “women” but didn’t really think much of it at the time.
All the talk of sex had me extremely horny so I was glad that it was dark outside. Blow jobs are my favorite and I couldn’t help thinking about Tobi giving me one. As if she were reading my mind Tobi asked me if I was into oral sex. I replied that it was my favorite.
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When she asked if I liked it better than intercourse I truthfully replied that I did. Her response was a big smile. She looked over at Trent and they shared a peculiar look.
“What?” I asked.
Trent looked at me with a rather serious look, “Would you like for Tobi to give you one of her specials?”
I couldn’t believe what I just heard and my idiotic response was “Huh?”
Tobi inched closer to me and sat as close to me as she could.
Her hand inched up my thigh as she whispered in my ear. “Would you like to see if I am as good as Trent says?”
I was looking right at Trent and he just smiled and nodded encouragement.
“Are you sure?” I asked to no one in particular.
Trent just leaned back to get comfortable, like he was getting ready to watch a movie or a ball game. At the same time Tobi began to wrestle with my swim suit and before I knew what was happening she had discarded them on the patio floor. I was naked in my hot tub with my best friend watching as his girlfriend was about to go down on me. I was nervous and a bit apprehensive.
Tobi stood up and took me by the hand. She guided me to sit on the edge of the hot tub. I did as directed.
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The place she chose provided Trent with the best view possible. There was just a little bit of light coming from inside the house, enough to be able to see what was going on but not enough to see everybody in detail. Tobi looked me in the eye, leaned in and gave me a moist sensual kiss and then started kissing her way down my neck, shoulders, nipples, and stomach.
“Find something to hold onto,” she said “because you have never had someone suck your cock like I am about to!”
She was right. Her hands found my cock and balls and began to caress them gently at first but with each passing moment her grip became firmer as she watched for my reaction. She was testing me to gage how much I could take and if I like her being rough with me. The more she squeezed the more I moaned until I shrank away in pain. She eased up a bit but continued to be rough with me. No woman had ever done this to me before. My balls ached, not from the pressure she exerted but from the desire to release the load of cum within. She began to lick the entire shaft of my cock as she continued to fondle and squeeze my balls. I was moaning loudly and had nearly forgotten about Trent. I opened my eyes and saw Trent watching intently as his girlfriend played with my balls and started to take my cock in her mouth.
She took in the head of my cock and I could feel her tongue encircle it inside her mouth. She rotated her head around my cock and continued to stroke my shaft and balls with her two hands.
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I was sure I was going to cum in seconds but she eased up. She squeezed my balls hard and I gasped out loud. The feeling of the impending orgasm died away. I looked down at her with a pleading look. I needed to cum. It had been almost a month since I had been with another woman and I was tired of playing with myself.
“What do you want Michael?” she teased.
“I want to cum in your mouth. ” I replied.
She just smiled at me and said “What do I get in return?”
“What do you want?”
“Mmmm, I want you to go down on me. ”
“Sounds fair to me. ” I replied.
“Good, because nothing is free dear boy!”
With that she took the entire length of my seven inches in her mouth and down her throat. It was the most erotic feeling I have ever had. I have had good blow jobs that I thought were great.
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But no woman had ever deep throated me before. Again, just when I thought I would blow a nut she stopped.
“Lean back and scoot your ass closer to me. ”
I did as she told me and she went back to sucking my extremely hard and aching cock. As she continued blowing me she began to play with my ass. I had had a couple women who would play with my ass and I liked it. In fact on one occasion an ex had even fingered me. At the time I didn’t let that situation play out because I wasn’t very experienced and thought it a bit weird, even though it felt good. Anyway, Tobi continued to play with my ass and I was getting more and more excited. She stopped sucking my cock but my dismay quickly turned to a different level of excitement as she began to lick my asshole. The feeling was fantastic. She started by slowly licking around the hole and then she would stick her tongue inside and would move in and out like she was fucking me with her tongue.
She was driving me wild and she knew it. My ass was well lubricated with her saliva when I suddenly felt a finger push inside me. I tensed a bit and she paused just long enough for me to relax.
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She slipped my cock back into her mouth and bobbed on my cock as her finger fucked my ass. This time when she sensed I was getting close she shoved my cock down her throat and simultaneously rammed her finger into my ass to my prostate.
I immediately exploded in the most intense orgasm I have ever had. As my orgasm subsided she continued to suck the last bit of cum from my cock and slowly removed her finger from my ass.
My orgasm was so intense I couldn’t even move for a few minutes. As I lay there basking in the fading remnants of my orgasm, Tobi moved up my body and I felt her lips touch mine. She began kissing me and I kissed her back. As I opened my mouth to her probing tongue I could taste my own cum. I had fantasies about a woman doing this to me and now it was happening. She had kept some of my cum in her mouth and now she was kissing me. This girl was a dream come true for me and I eagerly sucked on her tongue like it was a small cock feeding me its own cum. She seemed to be turned on by my response and our kissing became more and more sensual and erotic. Finally she broke our kiss.
She looked at me and gave me an impish little grin, “My turn. ”
She was wearing a one piece bathing suit that showed plenty of cleavage.
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She slipped the straps off of her shoulders and eased the suit down to her waist. Her breasts were beautiful in the dim light. The silhouette was enticing and I wanted to bury my face between them. I thought longingly about eventually putting my cock between them as well. She was putting on a show for me. She turned slowly to let me see her breasts from the front and the side. I was entranced by the sight of her. She then turned her back to me and slid the bathing suit over her hips revealing a very shapely ass. Finally, she bent over and completely removed her suit which joined mine on the patio floor.
She stood there for a moment and looked at me over her shoulder. It was very seductive and I longed to go down on her to return the favor of orgasm. As an afterthought I looked over at Trent and he was watching me intently. He seemed a bit nervous and for a moment I thought he was having second thoughts about what was going on. As I was looking at him I saw out of the corner of my eye that Tobi was turning around to face me. As she turned, her silhouette changed, revealing the ample curves of her breast and something else.
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What was that?
She moved closer and in the dim light I realized that I hadn’t just imagined it. Tobi had a surprise. At first I was totally stunned. I could hardly believe what I was seeing. Even in my shock though I didn’t hesitate, I reached out and grabbed her stiffening cock and slowly took it into my mouth. As quickly as I did this you would have thought that I was a veteran at sucking cock but in fact I had never done it before. For some reason I still considered Tobi to be a woman and so there was nothing revolting about going down on “her”. As I started to stroke and suck her I felt my own erection begin to grow again. I wasn’t just comfortable with sucking her cock, it excited me like nothing in my entire life.
I know most men would be disgusted by this situation: realizing that what you thought was a woman was actually a man and you had already been kissing “her” and she had just given you a blow job. For me it was different. After all, I had known her for six months, she was attractive, I had fantasies about her that led to wonderful sessions of self pleasure, and I really did like her. Of course it didn’t hurt that she had just given me the best orgasm of my life!
I was totally focused on pleasing her. No matter what she is, I will never think of Tobi as anything but a woman. Even the fact that I had her cock in my mouth would not deter me from thinking of her as anything else.
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I wanted nothing more than to please her like she pleased me. The fact that I had to suck a cock to please her didn’t bother me in the least. In fact I don’t think I could have been turned on more if she didn’t have a cock. The smoothness of it in my mouth was like nothing I could ever dream of. I loved running my tongue over the head of her cock, tasting the pre-cum as her excitement was building. Her cock was as large as mine if not a bit more so. I couldn’t take it all like she did mine but I eagerly sucked and licked her with the one goal of having her shoot her load of cum into my hungry mouth.
As much as I love to suck the nipples of a woman’s breasts I had almost totally forgotten those gorgeous orbs. Maybe my fixation with sucking nipples was because I wanted something in my mouth, something larger like the beautiful cock that was there now. I began to tingle as this thought crossed my mind. Had I wanted to suck cock but just didn’t realize it? I began to suck with more enthusiasm at the thought. I had to have her cum in my mouth. I began to moan as I stroked her with one hand and sucked with my eager mouth. Suddenly I felt her cock begin to grow in my mouth and then I felt a small spasm as her cock hit the top of my mouth and then she pushed it to the back of my mouth. Her cum shot down my throat and filled my mouth.
I swallowed as much as I could and continued to suck her wonderful cum from her shrinking cock. I slowly licked and sucked every drop. As she withdrew from my mouth I leaned forward trying not to let her get away.
“It’s okay baby,” she said “you’ll get plenty more if that is what you want. ”
“I do, I do” I said. The second I do was softer than the first. It was more of an affirmation of the first “I do” to make sure that I did say it and that I meant it. And I certainly did mean it. She was Trent’s girlfriend but I was in love with her.
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