My trans friend can’t stop fucking my pussy raw [FF]

After Anna and I fucked at her parents cottage things were a little touch and go between us.

We texted a few days after and I told her while I had no romantic feelings toward her and she told me while it was confusing for her since she’d never considered herself attracted to women, she had been thinking about it a lot and wanted to fool around some more.

I sent her some audio of me vibing my clit while thinking about us fucking and she sent me a pic of her cock, red and hard. I had asked her to come over the next evening and then she just didn’t show up. I was dissappointed because since then I’ve felt like a cat in heat, masturbating like crazy.

I didn’t hear from her all night, and the next day she told me this was a little hard for her because the way she’s been thinking about me and the things she wanted to do caused her some dysphoria. She said since the last time I just rode her while she laid there, a lot of her fantasies about me involved dominating me, like fucking me doggy style while I was tied up, which is not typically the way she has sex with men. She told me she’s a vers but is usually a bottom so constantly thinking about railing a girl with big boobs was confusing for her.

I assured her she was all woman to me and that I was absolutely craving for her to fuck me like that, but if she didn’t want to we could forget about it. She said no, she wanted to see me and said she felt maybe it was just something she needed to get out of her system. I said she could come over for supper and I`d let her take the lead, if she felt uncomfortable with sex and just wanted to hang that would be all it was.

She came over that night and it was HOT in my apartment as there’s a heat wave in my city. I wanted to wear a somewhat neutral outfit so she wouldnt feel too pressured sex wise. Short jean shorts and a t shirt. I was wet with sweat and the t shirt was sticking to my skin.

She came over wearing these cute heeled sandals and short dress. At first we just chatted as normal, no mention of sex. We ate pizza on my porch and had some glasses of wine. All the sudden there was this torrential downpour so we went inside.

She surprised me by cupping my ass with her hand and I knew where this was going. I was so excited to feel that dick inside me. I asked her if she was comfortable if I took my top and bra off since my tshirt was soaked from sweat and rain water. She said yes and I ripped them off. Basically I just pretended like everything was normal, asking if she wanted another glass of wine, walking around my apartment in just my shorts with my tits bouncing around.

I asked if she wanted to watch a reality show we`re both into and she said sure, she went in the living room while I got us some snacks and when i came back in she was stroking her cock. I asked if I could suck it, but she said she was still unsure, she wanted to get off but wasn’t sure about fucking my due to the dysphoria. She asked if she could watch me play with my toys. I was a little disappointed but I thought hey I`ll take an orgasm.

I grabbed a vibe from my room, sat across from her on the couch as she stroked and started grazing my nipples with it, and then my clit over my shorts. I was just watching her stroke her cock slowly, transfixed by it as my pussy ached to be filled.

After a few minutes I took off my shorts and started vibing over my panties, She gasped and pointed out how wet they were. “I need to be fucked right now honestly.” I moaned. She didn’t take the bait and I kept vibing. She asked if we could lie down side to side (basically she was in the big spoon position) and she started rubbing her cock on my butt while groping my tits.

I turned off my vibrator just trying to soak in the feeling as I could make out a sort of reflection of us in the TV. I told her I wanted to grab a dildo because I liked the feeling of my pussy tensing up around it when I orgasmed (I often just leave it in and vibe my clit till I come).

She held on tight so I couldn’t get up and really shyly asked if she could slip it in. I nodded my head and I felt her warm, veiny, throbbing cock slip inside me slowly, there was a sort of squeaking sound that came out of my mouth when she was all the way in which I think surprised both of us. I clenched my legs tights and she grunted.

When I tell you I was not ready for the way she fucked me I mean it. She started pounding me like she had a grudge against my pussy. She had one hand around my hips holding it tight as she thrusted like her life depended on it. Her breathing was so quick it sounded like she was running a marathon. I felt my face get really hot and I told her I wanted her to come inside me. There was no condom this time (I have an IUD) and I had been fantasizing about her come running down my legs for a few days.

She asked me to get on all fours on the ground and this time there was a little pain as she went in almost too deep. She started fucking me vigorously and bent over me so I felt her stomach against my back as she held my stomach tightly in her arms. I was getting absolutely, unequivocally railed while she grunted in my ear. Finally I felt her whole body tense up and she gasped as she stopped fucking me. Her dick was twitching inside me before she finally pulled away. I instantly stood up, as she sat on the couch, dick still semi hard.

A bit of come started seeping out, slowly on my thigh. I sat back down on the floor and reached for my vibe again. My clit felt kinda numb at first, but after about a minute or two I came.

I went to the bathroom to clean up and saw Anna was dressed. I asked her if she felt ok and she said yes but left soon after. I was worried maybe we shouldn’t have done that, but a few hours later she sent me a pic of her hard dick.

She has been coming over pretty regularly and fucking me rough. My pussy has taken such a beating. Anna has told me about prostate orgasms and how they make her come buckets. I told her I would be curious about at least watching her have one, maybe sit on her dick when shes ready to come and get filled up. Has anyone tried this?

Source: reddit.com/r/gonewildstories/comments/whwq8x/my_trans_friend_cant_stop_fucking_my_pussy_raw_ff

45 comments

  1. Please re-post the first story, seems like it got removed.. please keep sharing your stories with Anna

  2. “Her dick”. Yeah that’s a dude. Why is this a thing all of a sudden in the USA? Asking as a European.

  3. As a bi dude, I can confirm the prostate thing is completely true. I cum way more in my wife if I have a prostate vibe in there.
    The cum is different though. Clearer and less sticky than normal cum.

    I’m sure it would be similar with a trans woman.
    Go for it and let us know how it goes.

  4. You two might want to get a strapon – it can do wonders to alleviate dysphoria for her to wear one, and she might be hinting at you strapping her.

    You might want to head over to r/mypartneristrans if this is becoming a relationship. Good pointers over there.

  5. My (f31) boyfriend (M34) is the first partner I have ever had that enjoys any sort of butt/prostate play. I was so completely uneducated, inexperienced and clueless about any part of that sexual activity that he had to definitely guide me through it and of course I did some self educating, but the best thing has been hands on learning for me. Also a very patient partner is always helpful. My experience has taught me that after an intense and long session and he has had a prostate O (okay def several P-O’s 😉) he has an extremely difficult time getting hard and staying hard. So im not sure that you will be able to ride like you mentioned. Anywho, please feel free to let us know how it goes and if you want or need to ask anything please feel free to let me know!! Safe fucking xo 🥰

  6. Makes a ton of sense, she puts her penis in your vagina…. You got used by a mentally ill person

  7. This is one of the most wholesome and hottest stories I’ve read here. Absolutely love it 💗 Good for you guys!

  8. As a trans girl, reading this is really helpful and heartwarming, I see myself in Anna’s struggles and I love how you just want to make her feel comfortable, and how you see her as a girl 100%! Much love!

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