The story of a good friend of mine, he told how he sucked off a trans woman for the first time. However, it didn’t stop there.
The wild pleasure of sucking off a trans woman and receiving an oiled finger in his anus, which worked his prostate, made him desire for more. My friend decided to get fucked by a trans woman he had met through He decided to share with me this exciting story.

After my captivating adventures in Asia, where I was first sucked off by a trans woman and where I sucked off another trans woman for the first time myself, I found it hard to detach myself from the feelings that both ladies had evoked in me. For a long time I had fought against the exciting feeling that overcame me every time my anus was stimulated, but now I allowed my girlfriend’s finger more and more in my most intimate opening. Her fingers gave me great pleasure and made my cock squirt like never before. Still, I really wanted the whole cock of a real trans woman. I was not yet ready to share this with my girlfriend, this wild desire. Yet, I wanted more -I really did desire a cock inside me- and I decided to make an appointment with a trans woman who could deflower me and give me her milk.

After careful selection on the Internet, I stumbled upon a trans woman who received clients in the area where I lived. She was “in town for the first time,” it said, and specialized in “first-timers”; men like me who wanted to give themselves to a trans woman for the first time. The trans woman exuded a lot of class, and her photos were tasteful. She was of Latin American descent and spoke Spanish and a little English. Blonde hair and she likes leather clothes. She was very slim, had fairly large breasts, and in only one photo did I see, almost carelessly, her penis, which hung half stiffly beneath her while she was putting on her makeup. She was almost twice as expensive as other trans escorts, but she was very good-looking, very feminine, and the photos were all true to life, something that, according to many comments, was often not the case in this industry. In 2020, she was elected runner-up in a Trans-Miss election for her country. She exuded luxury and elegance in the photos. The appointment was at 2 in the afternoon. I rang the doorbell and a rather deep, yet feminine voice, admonished me to come upstairs. I entered the room and there she was, dressed in a sort of dark bathrobe and in high heels. She welcomed me, put me at ease, and as we sat down for a moment, her bathrobe gently fell open.
She was even more beautiful than the pictures suggested and had olive-brown skin, dark black, shiny hair and very dark eyes. Her mouth was set in red and her breasts were large and firm, wrapped in a black bra. She was slim, had long legs and a small ass, she was a very beautiful woman. She was wearing suspenders and black lace panties where I could clearly see a bulge.

Trans Woman was smiling

She saw that I was looking at her and even smiled a little shyly. She asked if it was my first time and what exactly I wanted from her. This was quite difficult because she spoke almost no English, only sultry Spanish. She told me that she didn’t suck herself, that she was saving that for her husband. She also didn’t let herself be taken. Again the same story, only her husband was allowed inside. With clients, she was rather dominant. She really enjoyed deflowering men as a trans woman. I got very excited when she asked if I wanted to taste her milk, or if I wanted to be deflowered by her. I said I was coming for the second, and she told me she really enjoyed deflowering men. ‘I love their look when they feel a cock inside them for the first time and I love to drive them completely wild,’ or something along those lines anyway. ‘No problem, I’ll give you my milk.’ She asked me to undress and smiled when she saw that my pole was already standing proudly upright.

She herself turned around and quasi shyly stepped out of her shorts. I saw her perfect ass and when she turned around, I saw her cock hanging limp but still present between her legs. ‘I’m not that far along yet, as you can see, and she pointed to her pole. ‘Would you like to taste me?’ I nodded shyly, and she pressed me to my knees. She pushed her cock to my mouth and put her hands on my head. I opened my mouth and tasted her. She heaved a small sigh when she felt my lips around her sex. Never before had I known a trans woman get stiff in my mouth, and I was experiencing this now. Slowly but surely her pole grew in my mouth, and soon she was making small fucking motions. Shortly thereafter, she began to lose moisture. She tasted nice and clean and encouraged me by saying little words and moans in Spanish. She took me by the hand and sat down on an armchair. Her pole had grown considerably and suddenly seemed quite large to me, at least about 16 cm and quite thick for such a slender girl.

‘You like?”, she asked me and I nodded. ‘Suck me,’ she said and sat up, spreading her legs and holding them with both her hands. I now had a stunning view of her cock and balls. Her cock was wet with my saliva and her moisture. ‘Suck me, please,’ she said, and I did. She took hold of both her ankles, she still had her heels on, and pulled her legs up. She opened her legs for me and I now saw for the first time also the dark pink circle around her anus. It was wonderful to suck her beautiful feminine cock, and I now felt how she also became really excited and made more and more cries. She also pushed my head further and further, and I took her further and further. She asked me if I had sucked yet and complimented me, “You suck very good.

I was giving head

A moment later, she put my hand on her balls and asked me to knead them while I sucked her. I sucked her and tried to give her everything. She was enjoying this straight man’s still almost virgin mouth. I enjoyed her transpire and the movements she made, the sounds I heard. After about ten minutes of sucking her, I felt she was almost on crack, her rhythm and breathing, her cries went to a crescendo. Her bra was still on, and I could see her occasionally touching her nipples through the fabric and caressing her full breasts. When I asked her if she wanted to bare her tits, she admonished me to be patient. Apparently, she was not yet ready to show me these treasures as well. She let me suck and she lost more and more moisture. Her cries became more and more intense, and she made me stop. Her cock was dripping with her pre-cum and my saliva. ‘I think I’m ready to fuck you now,’ she said and raised me up.

Oh, how I wanted to feel that beautiful, long pole, deep inside me. ‘Don’t worry, I’ll be gentle. I’ll fuck you like a man. You want it badly.’ ‘I’m hard for you.’ She laid me on the bed and willed me onto my back, so she could see everything clearly. ‘I want to see your eyes when I enter for the first time.’ That was my preference too. Dressed only in her suspenders, her high heels and her bra she was now, ready to deflower me. Her cock stood stiffly erect, glistening with juices, and smoothly she put on a condom. ‘You made me hot,’ she told me, ‘Now, I want to fuck and take your virginity.’
She positioned herself in front of me and took some lubricant, which she applied abundantly to my hole. A thick finger went in quickly and she smiled. Without hesitation, she put her cock on my hole and started to press. I was going to be fucked for the first time. She concentrated her pelvis and her cock on my most intimate hole, and her cock forced me open. She went deeper pretty quickly and I stiffened. ‘Don’t worry, the pain will be over very soon. Then only joy.’

She pulled back and slowly thrust herself deeper into me, slowly I opened up to her. This living cock was so different from anything I had felt up to here. This cock was alive and thrusting, searching its way inside. Nothing had ever been this deep inside me, and yet I couldn’t feel her balls yet. This was so intense, I felt her living, throbbing cock.
She began to fuck me rhythmically now, deeper and deeper. I felt a deep moan bubbling up inside me, and she instructed me to let go of everything. The cock went deeper and deeper, and suddenly I felt her balls slapping against me. Oh my, I was completely full and more and more pleasure came. I was being taken by a real trans. The pain was now out of the question, a deep and forbidden pleasure took its place. It is difficult to write down here what feelings I experienced. I felt a glowing warmth deep inside, an indescribable pleasure, I also felt every inch of that cock… the balls hitting my ass, the look in her eyes as she gave pleasure to a new man for the first time. Her thrusts became more intense, and I also saw now for the first time that she was enjoying fucking my virgin hole herself. She started moaning and stripped off her bra. Her tits were full and firm, her nipples standing up stiffly. They were big and long. ‘I take you, I take you. I fuck you like a man,’ she kept repeating.

I wanted to play with myself, she wouldn’t let me. My cock moved to the rhythm of her thrusts and lost an awful lot of moisture. The cries of pleasure I was moaning louder and louder, turning into a kind of roar. I was no longer ashamed of this intense pleasure and moaned to the rhythm of her cock. She was now taking me all over and fucking me wide open, the pleasure was getting too strong. She put my hands on her tits and let me play with her nipples. I was now receiving intense pleasure from both worlds. I saw a beautiful woman with big breasts and stiff nipples, I felt her cock taking me to heaven. Her face slowly began to leave with pleasure, and now she was not only thinking about the man being taken for the first time, but now she began to focus more on her own pleasure. Slowly she lost control of her body, she too wanted to release her load. ‘This is tight, this is tight,’ she murmured. ‘I’ll give you all of my milk.’ I wanted to stroke myself, to pull my cock, but again she wouldn’t let me. On the contrary ‘you come for me, you come for me, let it happen’, oh, I was almost in a trance. The intense heat began to spread from my anus to my cock and balls, it was too much for me, this could not be true? But oh, it was, yes, I was going to come because of her thrusts… I couldn’t believe it myself, I felt the warmth, the heat, my balls were contracting, my cock was erecting and first, yet another small stream of cum began to flow from my cock. I lay watching in disbelief, not knowing what was happening to me.

The trans woman saw what was happening, continued to thrust and suddenly a copious gulp of horny cum came squirting out of my cock, the intense stimulation of my prostate had gotten me this far. Jet after jet now spurted out of my cock as I felt my anus contract.
My seed reached her glorious tits, and she now smeared her nipples with my seed, almost in a trance, as she too was almost to that point… the contraction of my anus around her trans cock had also milked her cock… Her eyes became glassy and she too now announced her orgasm ‘your ass is going to make me come’, kept looking deep and pleadingly into my eyes and I felt her penis first stiffen some more and then lose its load of milk. The trans woman squirted her milk deep into my bowels and gave me everything. Since then, I have never been to a trans woman again. Somehow I’m afraid of losing control again, like that one time with her, when I cried out for more and was totally dominated by that trans woman with her big breasts and her thrusting pole, deep inside me.