[F]irst experience with a [T]rans woman

Within the past 8 months I have become moderately involved in the group sex and casual sex scene in my city. This is after about 22 years of Catholic repression so after my first boyfriend and I broke up 2 years ago I decided to go a little wild. I was invited to my first orgy (we call them play parties) by a female friend of mine and I’ve been loving going to them ever since.

My ex, Tim, was the first guy I ever had sex with, and his penis was probably about 4.5″, slightly below average. When I attended my first play party I was introduced to a handsome young gentleman named Jason who claimed to have a 7″ inch long penis. I was never really a big porn watcher so I was really impressed by his size when I saw it and it felt amazing when I let him inside me. It felt like being fucked by a horse and I loved every second of it. The guys at these events are very pickily selected and so douches who lie about their size or are insecure aren’t invited, so I think I’ve gained a fairly accurate perspective on average sizes and stuff. Surprisingly, until the story I’m about to tell, Jason was the most well endowed person I encountered at one of these events, so he was extremely popular with the ladies.

Fast forward to two weeks ago when I attended a play party about an hour outside my city in a small suburb. I went with my friend Kat who I usually go with and we were very pleased by how nice the venue was. A big, spacious, fully furnished house. Generally how these parties operate is there is a social area, where people meet and chat and have drinks and flirt. Then theres the play areas where people are performing sexual acts.

We took our coats off and entered the kitchen where people were drinking and talking and within no time I was being approached by guys. I hate to admit it but since Jason I have become somewhat of a size queen so after a few minutes of flirtatious conversation, I politely ask guys how big they are. I usually don’t turn people down on this criterion but its good to know so I dont end up with some guy with a really small dick.

About half an hour after arriving, my attention was caught by an attractive woman who appeared to be trans. I had always been curious about sex with a trans woman but most that show up at these parties are very submissive and only like guys. She looked cambodian or thai and was slightly tall. I approached her and she told me her name, Sophie. I didn’t want to be rude so I didn’t ask if she was trans but she divulged this fact to me a few minutes into the conversation. At this point I had had more than a few drinks and was feeling frisky, so I asked if she was packing. She smirked and told me that she had an 8.5 inch long, and very thick cock. I was blown away and instantly super turned on but kinda doubtful. (8.5 inches sounds like the length of a horse penis not the dick of a skinny asian chick). Fortunately she responded affirmatively to my request to sex and we entered one of the play rooms.

As we undressed, I discovered she was telling the truth, her fully soft penis was so much longer and thicker than my ex-boyfriends was when fully hard (kinda makes me feel bad for him lol, sry if you’re reading this Tim). I stroked her cock and made it hard before taking it in my mouth, but i could only suck about half of it! At first she wanted to fuck my ass (which I have done in the past but never with a big dick) which we tried for a few minutes with lots of lube. It was really hot but she could only put in an inch or two before it was too painful because of her massive girth. So instead, she fucked my pussy from behind. It hurt a little too and she still couldn’t put all her length inside but felt fucking amazing at the same time. After about 15 minutes she pulled out and asked me to perform analingus on her which I obliged too happily as she stroked herself. Then, I finished her off in my mouth and even swallowed for her (which I don’t usually do but she asked me to).

My friend Kat told me that a lot of the guys at the party felt a little humiliated that they were outsized by a girl which just made me proud to be the girl that got to take the big cock. Sophie told me she would be attending another play party in June so I’ll definitely be going, and I’ve been doing some anal training so that I can take more of her in my butt next time without screaming in pain!

Source: reddit.com/r/gonewildstories/comments/bv2qss/first_experience_with_a_trans_woman