I had sex with a new probable sex buddy the evening of May 23, 2021.
I’m 5’3″, on the chubby/thick side, dyed red hair, caucasian, 34F bra size.
So I’m at this dudes place, we’ll call him Thomas, he’s a guy I’ve met once before, years ago. The reason we met was because I found his ad on Craigslist (lol) saying he wants to lose his virginity and I liked taking v-cards. We met at a restaurant and chatted. Later on we kinda just decided not to do it, me for personal reasons and him because he wanted to lose his virginity to someone who is his actual girlfriend since he had not been in a relationship before. All good.
Years later (i.e. now) we end up chatting and decide to hang out. He’s not a virgin anymore at this point but also hasn’t been with too many women. He’s a few years younger than me (I’m 31). We’re sitting on the couch and we finish watching a show on HBO and I ask him to sit closer to me if he wants (he does). I ask him if he wants to make-out, he says yes. We start kissing and he bites my top lip then bottom lip softly. We keep kissing and I reach down feeling his chest, stomach then his pants. Tom is already hard and I can feel his dick through his jeans. I’m so happy about this. I absolutely love it when a guy is hard for me right away. I tell him to take his pants off and he does. I pull down his boxers. He’s got a nice 7″ dick, yay. I get on my knees and start blowing him. He moans a little and mumbles my name. Then I take off all my clothes and stand in front of him while he’s sitting and he looks at my naked body. Then we go to the bedroom.
We’re standing facing eachother. Tom’s body is very lean and toned. He’s 5’10” and I’m 5’3″ so I look up at him and say “You’ve got a really nice body” and he says “you too.” Then he tells me to lie down on the bed. He goes over top of me and starts playing with my pussy, rubbing my clit and fingering me lightly. “Yes….you’re so wet” I tell him I want his dick in my pussy. His dick has slightly softened so he tells me to suck it some more. I do and we’re both enjoying it, he’s lightly moaning and I am too. He asked “can I spank you” I said “yes” and he spanks me on my ass (I mean obviously, where else do you spank someone). “Are you a good girl?” “Yes” So I keep blowing him and I tell him “harder” and “harder!” as he keeps spanking me. I can’t wait to get to sex, I’m so excited I felt dizzy.
I tell him to lay down and he puts a condom on. I hop on top of him and guide his dick into my pussy. I start riding him and he grabs my neck, light enough that he doesn’t push boundaries but hard enough that I could tell he wanted to choke me a bit. As I’m on top, we can’t really get a good rhythm going and I already get tired (health reasons) so I tell him to fuck me missionary. He gets on top of me and starts thrusting. He licks my nipples and bites them— I tell him no biting, my nips are really sensitive so licking only lol.
I told Tom to choke me. He does, not too hard but not too soft, looking down at me. It was really hot looking at eachother from that angle. Then he leans down and kisses my neck and ear as he slowly and passionately pumped into me. It was soooo nice. As he keeps fucking me I felt like I was going to cry. The rush of endorphins was making my eyes well up. It was so wonderful to be having sex again and I was having all of these pleasant feelings in my body being activated. Being in so much pain all the time, I rarely get to ever know what it’s like to feel good. My whole body was trembling, in a good way. And it had probably been 3 months since I last had sex and that sex was pretty mediocre.
I kept moaning and moaning and he had to cover my mouth with his hand because I was getting too loud (upstairs neighbors). I wanted more at this point….I told him to fuck me doggy. Right as we got into position, he says “I think you’re gonna make me cum.” That really turned me on but I also wanted some doggystyle of course. So I tell him “what I want you to do is fuck me as hard and as fast as you possibly can, try to hold back cumming but cum when you absolutely need to. Don’t stop fucking me.” He obliges and grabs my hips and slams into me, pumping away. I looked back at him and it was so hot, seeing his abs and broad shoulders but being skinny at the same time. Seeing him pushing in and out of me. I was overwhelmed with joy and wanted to cry (but didn’t of course because that would be insane to do with a guy during your first time with him lol). Both of us were moaning as he fucked me and I told him how much I loved his dick and he said how tight my pussy was. I was in a haze so I can’t remember how long it all lasted but maybe like 3 – 4 minutes. I was getting louder and he reached to cover my mouth, I told him I’ll be quieter. I put my face on the pillow to moan louder. He said “I’m close” and I told him “please cum inside me” (condom on). And he keeps slamming into me, his moaning heightens while he orgasms inside of me.
He said he was sorry he couldn’t make me cum and I said not to even worry about it since I didn’t want to. I didn’t squirt because I had squirt a lot the night before from camming so I physically couldn’t squirt. Just for fun he fingers me for a little bit while I rub my clit. He gropes my tits at the same time. But then it turns out I kinda cum — I have a light orgasm with just a bit of squirt come out. Neat. But I definitely didn’t want to keep trying for more because it starts to hurt my insides (I know like wtf….squirting still a damn mystery).
We talk for a while and I go home.
The next day Tom messages me saying he had a great time with me. I tell him I’ve been thinking about the sex we had a lot and have been rubbing myself while reminiscing. He says “fuck same here” and tells me he’s jerked off and cum twice thinking about it. That makes me sooooooooooo happy. That’s super hot. He says he wants to see me fully squirt and I tell him I probably will next time.
We might be hanging out again this upcoming weekend :)
Btw I didn’t just know his penis size or his height by just eyeballing it lol when we were talking after and he told me his height and dick measurement.
Pics of me in submission history.
Source: reddit.com/r/gonewildstories/comments/nl2ps4/sex_with_a_new_friend_on_may_23_2021