Your first time with a tgirl

[maxpiazza]

My first time with a shemale was back in the late nineties in Milan, Italy.
it must have been 1998 or 1999, I remember watching a lot of porn back then. I was especially aroused by shemale scenes and there I started fantazising about fucking one of those beautiful creatures. My favourite scene was a very sexy brazilian shemale wearing a white navy officer hat being screwed by two studs on a sofa . Her name was Sabrina Hemolly and I really fancied her a lot. One summer night i was driving trhu a part of the city which at the time was well know for the presence of trannies walking the road. So i was looking around when i spotted a black Alfa Romeo parked along the road, the side door was opened and a pair of long sexy legs in black stokings were emerging from the car. I stopped my car near her and i looked inside: here there was the sexiest, hottest tranny i ever saw. She was Sabrina Hemolly indeed. I really can't believe my luck. I did'nt know she was in Milan but i always dreamed to found her somewhere someday because a lot of brazilian trannies were working as escorts in Milan at the time, and theer were always new girls coming over. When I called her by name and I told her taht i was "in love with her" because of her movies, she replied with a pleasant smile and told me it was time for me to stop wanking and "doing the real thing". So i followed her at her flat and had some of the best sex I ever had. I remember her rolling her eyes upwards like a demon while i was fucking her ass, like she often does in her movies, and that really made me crazy. From that night i had regular sex encounters with other beautiful shemales but i still remember her as my first "special" time.

[brian621]

I was getting in my car after work which is downtown and this babe with a micro skirt walked. She was working and he big thighs and round bottom looked good. I agreed to go to her place and when sh got in the car and grabbed my stiff cock she told me she was transexual.I agreed to go with her. Her cock was small and she did not get hard even when I sucked.But was a good fuck and I enjoyed the session

[StellaDixxie]

Top black girl, hung, uncut, my place. Best sex of my life. We went at it for about 4 hours.

[BentOverBitch]

My first time was about 15 months ago. We had been dating for a bit & She was a dominant shemale & I was a single submissive. So losing my shemale virginity was spiced with some s&m.

We were listening to music at her place and with no warning, Miss Stephanie had me kneel before Her and to get Her cock out. I had never touched another cock before and my hand was shaking. Part nerves, part lust! Ma'am was incredibly hung which excited me to no end. Or rather to my end. An average cock could not give me that feeling of submission I need. Once I took Miss Stephanie into my mouth I knew that being a great dildosucker = being a great cocksucker! Of course, it was more exciting because the reactions were true. She directed my cock sucking and was in charge the whole way. Her moaning just wanted me to please Her more. When Ma'am was close to cumming She ordered me to finger Her ass. She told me when She came to leave it in my mouth while jerking Her off. When She said now, I was to pull it out and have the rest on my face. I did and Her cum was so much sweeter than mine! A lot more of it too. Miss Stephanie smiled and rubbed Her cum all over my face and I was told to leave it.

I was commanded to suck Her until She became hard again which was almost immediate! She had me kneel on the couch cushions with my arms on the back of the couch. I was expecting to feel Ma'am's cock but was shocked to feel the hard stroke of a cane across my ass. I yelped and Miss Stephanie laughed and asked if I was surprised. She then laid another dozen strokes rapidly across my ass in what seemed like 2 seconds. I was whimpering and moaning unashamedly. My ass had been totally untouched in two years and so in a way, it was like the first time again for me. She came around to and grabbed my hair to face Her. She barked, "Do you want to be My bitch?" I nodded, which was a huge mistake. She slapped me HARD. I quickly stammered, "Yes Ma'am, I want to be Your bitch." She put a couple of big time, major pain nipple clamps on me and I gasped. I'm used to heavy nipple torture and these clamps hurt as much as any I had experienced. She then lubed me generously but roughly, fingering me crudely. Miss Stephanie told me not to move and left.

Miss Stephanie returned in about five minutes. She lifted my head up and began squeezing my tits hard and twisting the clamps. I almost passed out yet still remained hard. She then walked behind me and I prepared myself to be reamed by my first cock. Once again I was surprised to feel the smack of what I later found out was a thick wooden paddle. Ma'am gave me thirty or forty hard strokes and I bawled like a bitch. She then faced me and asked if I wanted to be fucked. I said only if it pleased Ma'am. She smiled and said good answer. I looked at Her cock and it was harder than I'd yet seen it. It was purple with arousal and the mushroom shaped head appeared eager for my ass. Miss Stephanie said that She expected me to be a great fuck at all times. I'm NEVER to just take it like a lazy bitch regardless of my physical condition. I was expected to meet Her every thrust with equal force. I agreed. She got behind me and spread my cheeks by digging into them with Her long nails. She also scraped my beaten ass with Her nails causing me to moan loudly. I was expecting Ma'am to ram it up my ass with a single, brutal thrust. However, She again surprised me by fucking me slowly and with just the head of Her massive cock. She said She wanted me to get used to that massive head. It hurt like hell but I was determined to please Miss Stephanie. After a moment She buried it in me and the race was on! Ma'am is not into gentleness and I was fucked hard for at least 10 or 15 minutes. Often She would pull Her cock out all the way but didn't miss a beat so I was really, really getting hammered. I hadn't been in such sweet agony in years! She changed positions, having me lay on the floor up against the couch with my legs pulled back near my head. Miss Stephanie ordered me to suck my own cock while being fucked! Never had such a thought occurred to me. But I'm built in such a way that I could pull it off. Or rather suck it off! lol The sight made Her fuck me even harder (if that's possible) When Ma'am was about to cum, She growled for me to cum and not lose a drop. When Ma'am came in a groan, She pulled out, cumming on my asshole, then shoving it back inside of me with Her cock. That caused me to cum with the best orgasm I'd had in years!!

Miss Stephanie smiled at me and said I was well on my way to being Her permanent bitch, which I was for over a year.

[chinotheonly]

I am new to the scene and I have been looking around to have my first Trans girl experience. I know that I have always been interested but I never have a chance to meet one. All I know is that I am ready and still waiting for my first time.