Gradually Loosing My Virginity [MF]

I was sharing this story with a chat partner earlier today and thought it might be a fun one to share here too. I’ll give a little bit of background here. This story took place while I was 19 and a freshman in college. Stacey was a Sophomore and we began dating on her 21st birthday. We had both been raised in Christian homes and were both intending on waiting until marriage to have sex. That may not be entirely true, but it’s what I told myself, but I also told myself I’d do pretty much anything outside of “sex”.

Prior to Stacey and I dating, my experience with women was limited to fingering one, making out with a handful, and under clothes fondling of breasts (in that order too). Stacey had no experience, I was her first boyfriend, first hand holding, first kiss…you get the idea. The story I’m sharing may read somewhat like a single encounter, but this was a progression that happened over the course of a few months.

Stacey and I started dating and quickly progressed to kissing, and kiss we did. I remember those days spending what felt like hours just making out. She was a natural at it, and we’d sit on her couch making out while a movie played in the background. Basically, if we were alone together, our tongues were in each other’s mouths.

My hands tend to wander when I get to kissing, and it was true back then too. My hands were exploring all around her body. Feeling her back, grazing around her butt, caressing her stomach, but taking caution not to go too fast. I’d get really close to various areas on her body like her ass, breasts, and pussy, but never directly touching her, but close enough that I’d just graze past them. Eventually I started feeling her breasts through her shirt and we’d make out as I fondled her. I remember the first time I tried to slip my hand under her shirt. She grabbed my hand and stopped me that time, but it wasn’t long after that that my hand was frequently under her shirt exploring her small breasts.

We also started grinding some during these times. She’d straddle my lap as we kissed and we’d make out, our bodies writhing in unison. I think we were too embarrassed to really acknowledge what we were doing, but we were both getting off. We’d both orgasm, but neither of us ever admitted to it at the time.

Near the end of the semester she moved out of the dorms and into a house off campus. Finally she had her own room, and we started spending more and more time just the two of us in her room in her bed making out. Our grinding continued but we started getting more and more physical. We hardly made out that I didn’t have my hand under her shirt fondling her, and I began slipping my hand down her pants to play with her pussy. I loved that feeling, slipping my hand into her pants, and feeling her lips, warm and soft, my fingers parting them to feel her wetness.

We started losing some clothes too. It started out that we’d take our shirts off while making out. It felt so good feeling her naked torso against mine, her breasts pressed against my chest, my hands being free to roam, and opened up the door for more kissing. I loved to kiss her breasts, sucking on her nipples. It was during this time I learned how aroused she got from me sucking on her nipples, and she’d almost always cum with my hand under her panties and her breast in my mouth.

We were still grinding too, and even that felt better without our shirts on, but we both were wanting more. Pretty soon, our make out sessions weren’t just being done topless, but we’d ditch our pants to. We’d lay in her bed spooning, me in a pair of briefs and her in her panties. At the time she wore these flannel string bikini panties and I loved how they looked on her. Feeling more of her flesh against mine was also an incredible feeling. We’d make out, hands exploring, and grinding while we made out. The feeling of her pussy grinding against my hard shaft only separated by two thin layers of material was so good and we had many orgasms like that.

Underwear also started coming off, not all the time, but from time to time and usually only one of us. Usually it was me taking mine off. I loved being completely naked with her, it felt so good, but also kind of dirty, which I liked. She wasn’t supposed to even see me naked, but there I was. We’d grind while making out with just the thin strip of flannel between us. At this point my orgasms weren’t nearly as easy to hide, so most of the time we’d grind and I’d cum on her stomach.

There were a few rare occasions where I’d convince her to take her panties off, we still weren’t having sex, but we’d make out, both of us completely naked, and we’d grind like that. She’d get so wet too and it amazed me. My cock would be coated with her wetness as we ground our bodies together. The lips of her virgin pussy would swell up and wrap around my cock as I slid it forward and backward between her lips, grinding on her clit.

We knew what we were doing was probably crossing lines, but technically we were still virgins because we weren’t having sex. As time went on, Stacey kept her panties on less and less until it was just normal for us to be in bed, naked together and grinding against each other. I remember teasing her sometimes, pulling my cock back through her lips, dragging the tip of my cock over her opening, and I’d pause there, her lips enveloping my head, and I’d tease her about how close we were to having sex. How all I’d have to do is slide my cock into her and we’d be having sex, and then we’d go back to grinding.

My teasing kept up, and I’d line my cock up with her pussy and lightly push so she could feel the pressure of my cock pushing against her opening, and I’d slide a little inside of her. Just the head at first, still toying that it would be so easy to have sex, I’d thrust a few times just letting the head of my cock dip in and out of her before going back to grinding. Looking back now, I’m not sure how we justified that we weren’t having sex, but in our minds at the time I think it was two fold. One, I wasn’t completely inside of her and two, it was just teasing the idea of it, and we’d go back to grinding on the outside.

The teasing continued though, and what had been just the head of my cock turned into the first inch, then two. Gradually the teasing was sliding my cock half way into her pussy. We’d even spend time with me thrusting in and out of her, but again, not all the way so it wasn’t “sex”. We kept playing this game and justifying it. One day we’re making out, playing this game and I’m sliding my cock partially into her when I realized I couldn’t slide in any further. I think we both acknowledged what was going on at that point and went with it. I don’t recall if we continued to have sex that day until orgasm, or if we went back to grinding on the outside, but after that, our external grinding games tapered off and we’d make out and have sex fairly regularly.

Since we were “good” Christians who weren’t supposed to be having sex, we didn’t ever have condoms. In fact, we discussed condoms a lot, and felt that we shouldn’t be having sex, and that buying condoms wasn’t in line with what we were saying we shouldn’t be doing. So for a long time, we had sex fairly regularly and never used anything. We’d have sex, and when I was close to cumming, I’d pull out and cum on her stomach. As misguided as it was, usually the week after her period, we wouldn’t pull out, but rather both assumed it was pretty safe and so during that week, she’d let me cum inside of her.

Stacey and I eventually got engaged, and went on to get married, and 20 years later, we’re still together.

Source: reddit.com/r/gonewildstories/comments/j607d9/gradually_loosing_my_virginity_mf