I never thought I’d see myself posting something like this, but anyway here goes nothing. A little about me first. 6 foot 4, 300 pound male with a very muscular build. I guess you could call me the typical all american jock as I have been into sports pretty much my whole life. Ive been dating this girl now going on 5 years and things really couldnt be better. We’re both 27, she’s about 5’4 120 pounds with a busty petite little frame. She’s got a great family who I see often, a great personality, and she’s drop dead gorgeous. The sex is pretty good, (I can honestly say I’m blessed below the belt), and my overall size makes it easy to throw her around in bed, (which she loves). Unfortunately, though, something has been missing, for me at least. I honestly dont know if I’m starting to lean toward homosexuality, but I literally can’t get dick off of my mind. All of my free time recently has been spent watching transgender porn, and even gay porn, and i didnt realize how turned on I could actually get. Watching that stuff and thinking about it has made me harder than Ive ever been, I mean seriously.
Anyway, every winter my girlfriends family all rent a house in a very popular ski vacation city in the US. it consists of a couple of aunts/uncles on her moms side and their kids plus the few significant others, ( me included). This year was my third time going, and this is where the story really gets interesting. My girlfriend has a cousin who is 18 years old and had just graduated high school the spring prior, on a town about 15 minutes from ours. I had hung out with him the first two trips and found him so easy to get along with, despite me being 9 years his senior. In fact we were almost inseparable to the point where my girlfriend joked about stealing me away from my “boyfriend”. I laughed it off and thought nothing of it then, but this year, with these newfound feelings Id been having, I was looking at everything differently.
My girlfriend, her parents, and I arrived at the vacation house a little earlier than other members of the family, and we shuffled in the door with our bags joined by flurries of snow into the open hallway. The house was beautiful, and we were informed by my girlfriends father that there were enough bedrooms for everyone to have their own, (her parents weren’t comfortable with me sharing a room with their daughter under their supervision), which was fine by me, considering id brought my laptop and was itching to us the wifi for some late night fantasizing.
I brought my girlfriends bags to her room, then brought my stuff to mine, and we all retired to the massive living room and drank a beer while her father began to build a fire in the majestic fireplace. Suddenly, the door crashed open and my girlfriends aunt, and family, shuffled in with their bags. I recognized the aunt as being the mother of the cousin i mentioned before, lets call him “michael” to make the story easier to follow. I gazed among the snow covered figures in the hallway and wondered where he was, until I realized he was right behind his mother, and looked very different from the last time I saw him. He was about the same size, but he had become so incredibly feminine. His long black hair had grown past his shoulders and was so silky and wavy it was straight out of a shampoo commercial. His face was defined but soft and smooth with perfectly trimmed eyebrows over big dark brown eyes. His small, pointed nose pointed down to his lips, which looked so soft, so much fuller. His narrow neck led to a very slim fitting leather jacket, and I swear his filled out ever so slightly, something I had never noticed before. His jacket ended well above his waist, and gave way to skin tight jeans. His legs were fucking incredible, slender but toned from the gym, and as he began to greet people inside, he would turn here and there while i gazed at his impossibly round, perky little ass. It was unbelievable. On his feet were a pair of chuck taylors, crusted with snow. I was among the last in line to greet him. And when we came face to face, I mustered a “How ya doing Michael? Its been way too long!” He smiled and I just about melted. Then, in a sweet, much higher pitched voice than Id ever heard from him, he said “yeah it has, youve know idea how much I missed you”. I reached out awkwardly to shake his hand or something like that and he said “comon” with his slender arms outstretched leading to light blue fingernails, which I had just noticed, and i stepped in. We hugged, strangely long, and strangely tight, until the realization of being surrounded by people hit us. I was never more aroused. God he was beautiful. God I was in love.
The last people to arrive were my girlfriends uncle, and his family, and we all sat in the living room by the warmth of the now massive fire, and caught up. I was trying to keep up with a coversation Id been having with my girlfriends father about football, but i couldnt stop myself from glancing over at Michael. He sat at the end of a couch on the opposite side of the room, legs crossed, and had swapped the jacket for a small crew neck sweatshirt, still pushed out just a little in the chest area by what I was sure were small breasts developing. Every so often he’d meet my gaze and I constantly held my beer on my lap in an effort to stop my 8.5 inch cock from breaking through my jeans. After about two hours of everyone discussing the itinerary of the next few days, people started retiring to their rooms a few at a time. Finally, it was just me and my girlfriend, who had cozied up to me on the couch. “Let me ask you something” I said. “Whats going on with Michael”? Without looking at me she responded “I know right?” “He is obviously gay, but my aunt and uncle are super conservative and they dont like talking about it, so we all try not to bring it up”. “Damn” I said. “I hope they support his decision at least, he’s such a great guy”. “Agreed” said my girlfriend, “but for now its best to just not bring it up”. After a while of sitting in silence, she yawned with arms outstretched and her hand landed on my still throbbing cock. “Mmm daddddy” she moaned. “I wanna feel you inside me daddy”. “Im sorry but Im exhausted” I responded. “Its just hard because Ive been sitting so long”. “Hmmph ooookay” she said as she started making her way to the big staircase. “See you in the morning”. “Mmhmm goodnight” I said, and made my way to my own room. Finally. I opened up my macbook and immediately put on a video of my current favorite pornstar, Natalie Mars (who I highly recommend), and immediately noticed a resemblance between her and Michael. My cock twitched as I watched her cock bounce and leak cum while getting fucked. I closed the laptop and instead thought about Michael while stroking my cock. I was officially obsessed. Afterwards I cleaned up, and thought about him some more until I fell asleep.
The next few days were pretty much similar to the years before. There were plenty of fun activities like tubing, skiing/snowboarding for some (I did not partake), going out to the local steakhouse for a good dinner, etc. It was startinf to seem as though my girlfriend and I were drifting apart, while Michael and I were closer than ever. I still made it a point not to bring up his sexuality, though, as not to make things awkward. On the fourth day of the weeklong trip everyone decided to go take a hike to a local peak that apparently was famous for its views. I declined, as I was feeling a little out of it from drinking the night before. When it seemed as though everyone had left, i made my way slowly up the stairs and when i got to the top. I noticed a flash come from one of the bedrooms at the far end of the hallway. Michaels bedroom. Realizing that I was not the only one home i crept as quietly as possible until i could see through the crack in the ajar door.
There was Michael on the floor. Hair in a bun, with nothing but a black lace bra on and very high heels, on all fours next to a mirror. He had his back impressively arched, with his perfect ass sticking up in the air. I could see his pretty little pink asshole, (far nicer than my girlfriends), and his legs were pressed together with his clean shaven balls and his 5 or 6 inch tucked behind them. He was taking nude selfies. I pushed open the door a little bit and the creak jolted him. “Holy shit, holy shit” he yelled as he ripped the comforter from the bed and wrapped himself in it, not before I noticed his beautiful cock spring up in the air. “Fuck fuck uhhhhh”. He searched for words. “Look man, its totally okay” I said. “I knew something was up, shit, everybody does” He looked frantic at first, but started to catch his breath and calm down. “So whats up Michael? Youre gay right? Theres nothing wrong with that” I said. “Thats what everyone thinks” he shot back, “and thats not what I am”. “Okay, okay, then talk to me” I said. “You know what being trans is? ” he asked. “Ugh sort of” i said, trying to play ignorant. “I know I was born a man, but Im really a woman. I think like a woman, I act like a woman. Ive always felt like a woman. I have the desires of a woman.” I ached for her. “I understand completely” I said. The tension eased. “You look really really good”. I didnt know how else to say it. “Like as a woman i mean” She blushed. “Thanks, Ive been doing hormone therapy since I turned 18”. I thought about her ass and tits and her feminine looks. “Yeah ive noticed some things are uhhh…different” I stammered. She chuckled. “Can I tell you something? I know youre straight and youre dating my cousin and you are a lot older and i dont want to make things awk-“what is it?” I demanded, trying to conceal my excitement. “Well…here goes, ive had a huge crush on you for years now and even before all this I would think about being with you all the time, I still do” she said as her eyes became seductive. “Michael, youre all I think about. Ive never been so attracted to anyone” i said as i took a step closer. She lowered the blanket a little and said, “ive never said this before but call me Mandy when its just you and me, okay?” “Okay Mandy”.
“So you really think I look good” Mandy asked shyly and flirtaciously. “Mandy, youre the most beautiful girl Ive ever seen” I responded. She gave a smirk and dropped the comforter. Her bra was pulled down slightly, revealing her tiny tits and puffy little pink nipples. Her thong was pulled to the side of her circumcised cock, which was so hard it curved upward. Her thighs and calves were shaved smooth and were flexed slightly from the heels on her petite feet. I walked up to her and her head was about level with my chest. I pulled her head toward mine and we made out passionately, while she let out soft moans and whines in pleasure. As she ran her hands down along my massive frame, i ran mine along her smooth skin and curves. I unclipped her bra and squeezed her breasts. Then, i kissed my way down her neck and chest and caressed her soft nipples with my tongue. She let out a squeal, and I could feel goosebumps wherever my hands were. “Ohhhh fuck DADDY”. It was a million times better when she said it. I wanted to explode. I kissed lower now, down her flat stomach, then her waistline. The taste of her skin was like a drug. Lower even, I kissed and ran my tongue against the stubble below her waist, until i felt her cock touch under my chin, wet with precum. There was a natural smell of sweat and skin from her cock and balls and I couldnt get enough. I was on my knees now, looking up, straight in her eyes. “I wanna suck your cock, Mandy” I said. She moaned and bit her lip, nodding at me. First i ran my tongue from her balls along the base to the tip. She tasted fucking incredible. I could taste the saltiness of her precum too. Then, I took her in my mouth and was surprised by how much she filled it out. I ran my hands up to her tits as I sucked and slobbered on her rock hard cock. Periodically, I would pull it out and use my tongue to play with head, or take one of her balls in my mouth while i stroked her. Her moaning intensified. “Oh fuck, where should i cum? She asked frantically. “I want it” I said while tonguing under the head. “MmmmMMMMM IM CUMMING” she said, and her cock started to pulse. Hard. I picked my head up a little to make sure it was pressed hard against my tongue, and then i felt it. Warm jets of thick cum filled my mouth with intensity. It was difficult to contain. Mandys cock wrenched and throbbed and jolted and the cum kept coming. I couldnt believe how much there was. Mandy whined and squeeled and shivered, while i firmly grasped her ass with my lips tight around her. When she was finished i slowly pulled my lips off of her, while keeping her hot cum in my mouth. I loved everything about it. The taste and consistency. I savored it for a few seconds before swallowing it whole, which wasnt an easy task. Mandy collapsed backward on the bed and I laid next to her, kissing her body again, and then her mouth. “Mmmm i taste good daddy” she whispered. Then she ran her hand down to the massive bulge in my jeans. “HOLY SHIT, is that…real?” She asked. I chuckled. “How have I never noticed? The longing in her voice was unmistakeable. I reached down to her cock and couldnt believe it was rocl hard again. Then, suddenly, a sound from downstairs had us both on our feet like a jolt of lightning. The front door. They were home. Luckily I was still dressed so I kissed Mandy goodbye and made for the door. Once in the hallway I heard her lock the door behind me and I hurried to my room. I was barely inside when I heard a knock at the door. “Hey, its me”. It was my girlfriend. “I got you one of these cool sodas we found after the hike” she called through the door. I let her in, “thanks babe” I said. “So whatve you been up to all day?” She asked. “Eh not much, just havent been feeling so hot” I responded sheepishly. “Aww, come here” and as she kissed me I prayed she wouldnt taste her little cousins cum, which still coated my tongue. “Im gonna go help get dinner started, you stay here and rest” she said. “Thanks babe, maybe Ill come down in a while”.
Well, here I am now and its the next morning on the fifth day of the family vacation. Im lying in bed typing this all up and honestly I do feel guilty about cheating on my longtime girlfriend with her much younger cousin, but the way I feel about Mandy is like nothing Ive ever felt. I havent seen Mandy or anyone else since yesterday, since I havent left my room, but needless to say, today should be interesting. I’ll keep you posted reddit. To be continued.
P.S. Thoughts, comments, and PMs are more than welcome! :)