[MT], My first time orgasming inside of someone

This happened over two years ago and was also the first time I tried anal (giving).

To keep it short I’ll skip on many of the details on how we became friends, I was new in town and I met her on tinder in which we instantly became friends as she is a ripped, trans, dom, 33 year old, 5’10, Venezuelan and Italian American programmer and I’m black, 6’0, 240lbs, 25 year old, black engineering student with an average build. I also according to her, have a thing for female bodybuilders as well so that’s what drew me to her even though we agreed it will be platonic because of our preferences but we have good chemistry as friends.

Fast forward months later, we had already hung out a few times with nothing happening and while we were in a PS4 party with her and her friends, they were all wanting to switch to Smash and Mario Kart and play something called DWI which involves drinking an entire drink before starting to race and then drinking another every other lap. She invites me and tells me to bring a change of clothes since she doesn’t want me driving home while drinking since I live 35minutes away from her.

This was the first time I ever met her friends in person since our schedules are all different. It was also commented that I’m the token cis straight guy in the group. So we start playing Smash. I get destroyed in that of course since I don’t get to play it much. After a while, her friends start to head out and say they will play DWI back their places since they lived relatively close and decided to Uber back. I tell her that I’m going to change and she says she does as well. When I come out, I see her wearing circular, thin, black rimmed glasses, a tank top, and some leggings. I went commando in a tshirt and some shorts. I commented on how she looked like the latin version of Harry Potter which did help in the race.

I don’t remember how exactly it came to happen but we ended up on the topic of what we like when it came to what she seriously looks for in men and what I look for in women since she knows that I only want to be with cis women and comments on how it’s not transphobic because I don’t broadcast it. She expresses her interest in men being only bottoms, shaven face, with them being shorter and not as husky as me and that they also have to like dick which is the opposite of me. I’ve even mentioned to her that I never even orgasmed from sex and that none of the women I’ve been with noticed since I usually stop after they cum once or a few times. She looked at me confused and concerned even after I tell her that it’s a blessing because I can keep going. Then she tells me that the straight community is weird. She asks if they have asked what i liked and if I tried anal before, which I respond with no as I do what I can to make them cum until they can’t anymore. I then realize that no one has ever expressed or mentioned anything about me cumming. She takes a deep breath and looks up on Google to find out that I’m a service dom. She moves closer to me and then tells me, “I bet I can change that cum issue of yours”. I playfully respond to her “I doubt that but it would be fun to try”.

We slowly start making out while trying to move towards her bedroom. I then pick her and have her legs wrap around me so that we could move faster. She then starts laughing and mentions that it was her first time being carried like that.

I lift her shirt up to see her amazing body and realized that she’s even more ripped than I expected. I slowly start kissing her down her neck, have my tongue play with her nipples while grabbing on her breasts, kiss her abs, and then down to her thick thighs with her breathing becoming more heavy as I do. She lifts my head up to tell me that she wants to feel my lips on her skin and that she needs to adjust her dick so that it doesn’t get in the way or make me uncomfortable, so I make her flip over onto her stomach so that I can kiss her down her back. I then get to her pants and start to pull them down enough to only where her whole ass is exposed. Before I could spread them, she told me that she was nervous for me to be back as she’s only been eaten out once and hasn’t shaven back there. I told her not worry about it. I felt my mouth watering as my hands were grabbing her big, slightly muscular, soft, natural, ass. I spread them apart to reveal her brown and slightly hairy asshole. I never cared about what it look like since I usually would eat ass when I’m with cis woman, but seeing her asshole a little hairy made me really stiff. I then have my tongue dive into as I try to push it inside of her. After a while she stops me to face me while holding me by my chin to tell me that I gave her the best head so far and kisses me.

She then tells me to get up and lay on my back so I take off my shorts as she straddles me with her leggings still slightly on but with her ass still out she starts kissing me while stroking it and rubbing it against her hole in which then she tells me, “I’ve never done this before as I’m always the one in your position and you’re significantly bigger than me”. I tell her that we can stop if she’s not comfortable. She adamantly tells me no and mentions that I’m now having sex the right way in that both people are being pleased. I tell her that I obviously didn’t bring a condom, in which she responds, “do you want one?” I say no and she tries to slowly forces it inside of herself without lube right when I said that moaning in pain and pleasure. I try to mention if she needs lube which she shushes me as I feel her ass opening up a little and new wave of pleasure hits me as she starts taking nearly half my length. After a little bit, I notice that she starts shaking and clenching her ass which I ask her if she came. She manages to say “uh-huh” while gasping.

She then tells me, “now it’s your turn”, in which I begin about to say no because I thought she wanted to switch places but instead I see her take out my dick and moves into a squat position over it. She then looks at me with a determined look in her eyes and slowly comes down on it in which we both and say two different things. She says, “it feels like it’s in my intestines”, and while I say, “Ive never been this deep before”. She then kisses me and holds my face while she bounces herself on my dick. Not too long in, I feel my dick swelling and I tell her I’m about to cum. She then stops and takes it out of herself for a second then she says out loud, “Actually, you’re going to cum inside me”. In which she takes the full length of it 3-4 more times and I pull her down on it, my toes curl, and I feel myself shooting my cum inside her ass and comments that she can actually feel my cum. Afterwards, she asks me if I want to spoon and I tell her that I’m still hard so I slide into her while we are spooning and with my cum still inside her and she mentions that we both in a joking way lost our virginity and we keep talking until we fall asleep.

We are still friends to this day. We also had a threesome (another story) and she has recently told me that she hasn’t wanted anyone else to top her. She also has expressed that she wants me to become addicted to her ass and anal in general for some reason

Source: reddit.com/r/gonewildstories/comments/vf3aly/mt_my_first_time_orgasming_inside_of_someone