This happened about five years back when we were both 18. A close male friend of mine was pretty bummed out about the fact that he was still a virgin going into college, and after some joking between the two of us (and, tbh, a lot of flirting) I decided that I’d help him out with that problem and take his V card.
I asked him if he’d be down with it and he very enthusiastically jumped at the chance after he spent a few minutes asking me if I was joking. We settled on a day (a weekday in July, when my parents weren’t home) and I told him to come over and to bring condoms.
When he showed up at the door that morning, I answered wearing nothing but a tank top and a pair of black lace panties and pulled him in by his shirt for a kiss. Tbh I think it might’ve been his first kiss as well, because he kissed me back very awkwardly, but after some sucking on his bottom lip and slipping my tongue into his mouth a few times he seemed to get the hang of it 😂 we made out in the kitchen for a few minutes before I took his hand and had him follow me to my bedroom.
of course, being a gentleman, he asked if he could eat me out first because he wanted to make sure I came before he fucked me. I obliged because I loved being eaten out and never had a boyfriend who had ever been into it, so I laid back on my bed while he knelt at the side with my legs over his shoulders and started deeply and enthusiastically making out with my lower set of lips. Honestly, he wasn’t super great at it but his enthusiasm and moaning was enough to get me there and after a few minutes I had my fingers in his hair as I came with his tongue inside of me, and I think that made him happy because he moaned through the whole thing ❤️
After I came, I asked to return the favor for a little bit and flipped on the bed so I was facing his crotch as he unzipped his shorts and tugged then down. He was already rock hard and had some precum leaking from his tip. He wasn’t the biggest (if I had to guess I’d say about 5 inches?) but his cock looked really nice and I could tell he had shaved it just for me so I gave it a little kiss and then began stroking it while I smiled up at him, he was just staring down at me with this cute expression and it made my heart do a little jump.
I popped his cock in my mouth to get it nice and wet, sucking the head while I stroked his shaft, before telling him he could thrust a little if he wanted. He cautiously started pushing his cock into my mouth and I opened up so he could push it in smoothly. His little moans were so cute as the bottom of his shaft and head slid against my tongue, I made sure to keep my lips against his shaft for maximum contact and I could tell he was really enjoying himself because he started to pick up the pace and thrust deeper, eventually hitting the back of my throat and making me gag a little and pull away. He apologized, but I told him it was fine, and if he wanted to he could put the condom on and fuck me.
He got really excited which made me giggle and went to his shorts to pull the condoms out of his pocket. When he tore them open, I saw he was having some trouble getting one on so I went to help him roll it down since I’d done it for previous boyfriends in the past. Turned out they were a little big on him, but we had to make do because we were both so horny and didn’t want to stop ❤️
I got back on the bed, at the side of it with my legs spread so he could enter me easily while he stood at the edge of the bed. As he pushed in I felt him spreading my pussy apart, and even though I hadn’t thought his cock was that big it had been a while since I’d last fucked and the feeling of having my pussy stretched open felt so good. He asked if I was okay, I moaned out a yes and reached for his hand to hold it while he lost his virginity. He started fucking me, slowly at first, then picking up the pace as he got more used to it and I got his cock wet with my juices. Honestly, it felt really good and it was nice to do it with someone I already trusted so much inherently. The first time I came around his cock, he leaned down to kiss me as I was cumming and it was so wholesome!!!
We fucked for about forty minutes or an hour, which I thought was really surprising considering he was a virgin. We swapped positions a few times, moved on to the bed for proper missionary with my legs wrapped around him, flipped over so he could pound me in doggy for a while, then went back to me being on my back with my legs over his shoulders so he could fuck me really deep. I had came a few times at this point and was starting to get tired out and sore so I was pretty much cheering him on to cum at that point, saying stuff like “please cum in me, I want to feel you cum,” and all that. He eventually told me that he was having trouble with the condom and couldn’t cum, or that it might’ve been nerves. I asked if going back into my mouth would help (honestly my pussy was pretty sore and used by this point haha) and he agreed, so I scooted up on the bed a little bit, had him come up with his knees on either side of my head and take the condom off, then told him to fuck my mouth.
He pushed his cock into my mouth and started slowly at it first, then as I sucked him and moaned around his shaft started picking up the pace, really holding my head and steadily pumping his cock into my mouth. Idk if it was because he took the condom off or because it was in my mouth, but this seemed to do the trick for him and pretty soon he told me he was cumming. I grabbed his hips and held him in my mouth and sucked while I rolled my tongue along the bottom of his shaft and pretty soon was rewarded with his hot cum pulsing into my throat, which I did my best to swallow as he moaned and pulled my hair. Eventually he slowly pulled away and I let his cock slide out of my mouth with a little pop, trying to keep his cum from spilling out.
Afterwards we cuddled naked for like an hour, making out and giggling and chatting while he thanked me profusely and we talked about how nice his first time was. Eventually it was getting close to when my parents come home from work so we decided to leave and go to a park nearby, and we held hands there and walked around and made out in the woods for a while. It was all super wholesome and sweet. He dropped me off that night and texted me immediately when he got home thanking me for such a nice day, I told him I felt the same.
We ended up seeing each other for the rest of the summer, not officially dating because we were both going to different colleges in the fall, but definitely “a thing” and we definitely kept fucking as much as we could. it was a really nice time in my life that I look back on fondly, even if we’ve both gone our separate ways and live in separate parts of the country now.
Source: reddit.com/r/gonewildstories/comments/ypsov1/fm_i_took_my_friends_virginity_the_summer_before
This was so loving and wholesome, which was evident from both of your reactions. You’ve set an extremely high bar for all his future lovers
I see u were looking for a cock nd u helped him…
My first time I lasted like 3 hours
I can’t believe he lasted that long
Loved this.
My first time, I fucked the girl for about 45″, in a variety of positions.. She was all sweaty and worn out. She asked me to stop, as she couldn’t take it anymore. I was really glad I wasn’t a virgin anymore, and it felt great, but I was somewhat bummed out that I had not had an orgasm.
Really great hearing this. Wish i could get a friend like u
You should post on r/gonewholesomestories
More then likely if he was smart he jacked off beforehand to get the dangerous one out first. That first nut in the day is lethal and has a hair trigger at that age
This is so wholesome ☺
Lucky guy