A submitted story of a man who goes on a trans dating meeting with two cute ts women. Pictured is Michelle.
The ad in the local “underground” paper said, “2 hot shemale sweethearts looking for inexperienced open-minded man for exciting new encounters….” It added a few brief descriptions etc. I thought to myself. “Why not, you’re open-minded and adventurous?” So I called them and wondered about the details. I’m not entirely new to the scene and have dabbled a bit in being at the bottom or receiving end of anal, and although I’ve never traveled the shemale route, it always fascinated me. I’ve seen many photos of shemales that were amazing…. Could I get lucky here and join a few hotties? We chatted for a while; Michelle and Jane were their names, and Jane gave me descriptions of themselves and what they were looking for. I provided all the “details” about myself, which met with their approval. I told them that I had never been with a shemale before, much less two at once, but was always very curious and had a definite interest in exploring things.
The day for the trans dating has come
This was exactly what they wanted. We exchanged a few photos via email and an afternoon get-together trans dating was planned. Michelle described herself as petite with long dark hair, a tight little body with a killer ass as she portrayed it. Jane was tall with larger breasts and curvier. I decided to take the afternoon off work as it would be the most convenient time for all of us. For obvious reasons I was nervous as hell at the twenty-minute drive to their place, I mean, what if the pictures were far away, and it would all turn out to be a disaster. I knew soon enough when I arrived at their tower block. After pushing their door pin, a sultry voice welcomed me to their apartment. My heart raced as I rode the elevator up to the 16th floor. A short knock and slowly the door opened welcoming a smiling little lithe she-male. “Hi, I’m Michelle, and this is Jane.” Taking me by the hand, she quickly closed the door behind me. She had been quite accurate in her description and actually looked quite warm. She was about 5’2 or so, maybe 110 pounds with a short skirt and tank top that showed off her poking small breasts, streaked black and auburn hair. Furthermore, she had cinnamon skin.
Hard to believe she wasn’t a “real” woman. Jane was much taller, close to 6 feet and voluptuous, with long dark hair and much more “woman” to be sure. Both were totally approved! We exchanged some small talk, but they seemed far more interested in getting “up close and personal”. I had mentioned taking a quick shower during our phone call, so after the introduction and such, that was where I headed. “Hurry up though… we’re waiting.” They say. So I go and take a quick shower, thinking about what’s to come. Standing in the hot water, my cock began to stiffen at what was to come. After I dried off and wrapped the small towel around my waist, I stepped out in search of my new friends. “We’re in here.” A voice called from the adjoining room, which turned out to be a bedroom. I stepped inside to find the two eagerly awaiting my arrival, they were immediately on me. “So do you like us, do you think we’re sexy and hot?” They ask. “Yes, much better than I expected,” I reply.
They don’t waste time when they embrace me. Their well-groomed hands roamed all over my newly showered body, my erection, removing any doubt about my interest in trans dating. This pleases them, as Michelle is the more aggressive of the two, yanking at my towel to swallow my now fully erect cock. Jane peels off her clothes and shows me her full breasts as Michelle slips out of her tiny skirt. When I pull in another direction, their eager mouths wanting me, I willingly oblige. Michelle climbs onto the bed and almost pulls me to join her. Jane, behind me, hands roaming up and down my body, reaches down to slide her red nails along my erect, squirting cock. I can feel her full breasts against my back… her dick pressing and exploring my ass cheeks. She guides me towards the sales floor. We never got into details about what we were going to do or get into. They just said we’ll have fun and hot. I look over at Michelle kneeling on the bed, showing off her rather large, fully erect cock…. I stare at it as she beckons me to join her. With one hand brushing over it, she taunts me and tells me how she wants to fuck me with it. It’s big and thick and long… just waiting for me.
The next thing I know, I’m on all fours with Jane lying down and I’m being guided firmly against her, waiting hard. Everything happens so fast… I don’t have time to decide what I want or what I’m comfortable with… it’s not my decision to make… it’s what they want and will do. “Come up here and suck it. Take me in your mouth.” I’m told by Jane. I move up, perhaps a little reluctantly, but comply with her requests and take her into my mouth, at first concentrating only on the head of her cock and letting my tongue swirl around it. She’s not big, but hard and nicely shaped. Holding the base in one hand and sucking her up with saliva, I take her deeper into my mouth, alternating between a firm grip in my hand and sucking and licking the underside of the head. Judging by her moans, she’s enjoying me so far. Michelle has other plans and is about to tell them when she moves in between my legs and pushes them wide apart, exposing my ass to her. With a liberal squirt of lube into my ass, she wastes no time… no time to ease me into this… pressing the fat head of her cock against my tight but smooth ass, she pushes in…. In a full stroke, she is inside me. I gasp loudly at the suddenness of her entry. “Ohh… ohh!” I let out as she repeats her motion. I try to continue pleasuring Jane, but Michelle’s attack on me has surprised me so much that I can’t.
She pulls back and literally throws her thick hard smooth cock back into me…. Now she is gripping my hips for leverage. Jane moves away to join her as she starts urging her on, even more, slapping and rubbing my ass. “Is he tight enough? Take him good?” Jane wants to know. Michelle nods and says between breaths, “Oh yes he’s tight. You’ll like him too!” “I want to fuck him…. it’s my turn.” Jane demands. I feel completely used by them. Michelle drives me a few more times, then pulls out, leaving me gasping, if only for a second. A shift behind me and a smaller but firm cock is nicely eased into me… slower and somewhat calmer as she completely buries her tool in my soaked asshole. With long nails she traces them down my back as she fucks me slowly and steadily… but just as her partner Michelle had done, Jane soon finds her tempo_COPY grunting with each stroke she holds me firmly within her grasp. Faster and faster, she is close to cumming as she effortlessly slides in and out. “I want to ejaculate inside him.” She announces. “Oh fuck… oh yea!” As she releases load after load into me, her hips slam against my ass. For a moment she rests, her cock still inside me… her breathing slows. With some suddenness, Michelle moves her aside and makes me turn onto my back…. She wants to finish what she started earlier. She pulls close to me and starts stroking her still thick and hard cock, adding more shine to her shiny shaft. Without warning, she slides effortlessly into my well-oiled asshole… I gasp at the fullness of her cock, it surprisingly doesn’t hurt, she just takes a breath with each stroke as she fucks me over and over. … humping me with ease.
Jane has come to my side and is squirting lube all over my engorged cock, and Michelle quickly seizes the opportunity to start stroking me… with a firm smooth grip she slides up and over my entire cock… Jane joins her, alternating between massaging the balls and teasing the underside of the cock head. I can feel myself starting to build… with the constant work over my ass, the 2, 3 and sometimes 4 hands on my cock I can’t hold on any longer… I had wanted to fuck one of these two first, but…. With a vocal moan and in harmony with her deep penetrations, I start a huge shuddering climax. “OOhhhhhh…. fuuuck, that’s it….” I practically scream in pleasure, spurting my hot semen way up and over me. Jane milks me and continues to squeeze every drop of pleasure, every drop of semen from me. Michelle looks a total lust in the face…. Then announces that she is there too, and with long quick pumps she pulls out and releases pleasure spasms all over me, cumming and cumming…. The look of pure pleasure, the look of satisfaction, tells all. “Oh baby, that was good, you have a nice ass, nice to fuck.” Michelle adds. “Did you have fun with us?” They ask. “Yes, it was good, you were both good. I’ve never had my ass done like that before.” I explain. “Well, then you’ll be back again?” Jane asks. “Maybe you can fuck me or Michelle; she has a nice, tight ass. Don’t you think?” Says Jane. “Yes she does, and yes I would like that.” “Next time then baby… next time!”
