The one where I lost my virginity to a friend’s sister [MF]

Third story in my chronological series. I tried to keep this one shorter than my first two novels, but as you can see it still came out pretty lengthy. If you’re just joining me and want to read my first two tales of my first handjob and blowjob, check my profile. Just be aware they are extremely long.

I was 18 and it was the summer between high school and college. I had been a late bloomer and was new to my sexual career, but I was thus far off to a very strong start. Shortly before graduation, I had gotten my first handjob, followed almost back to back with my first blowjob. I can safely say, looking back, that they were 10/10 first time experiences and almost ruined me with peaking too early. Luckily, fate had another good experience coming my way for my first time having sex.

So there I was, recently graduated and very motivated to cash in my V-card, with no idea how to go about doing it. I didn’t want a relationship, and for most girls I had gone to school with, that seemed to be a prerequisite. I had several good female friends, but none that seemed like they would be good candidates for having casual, first-time sex with.

I was, at that time, getting semi-frequent, life-changing blowjobs from my classmate, Elise, but she was clear about wanting to remain a virgin. Our relationship was very casual. About once a week we’d be meeting up so she could eagerly suck my dick and swallow my cum like her life depended on it, but we didn’t even kiss. It was a true fuck buddy scenario but for blowjobs only (suck buddy?). I was very happy with that arrangement, and it was keeping my out of control teenage hormones somewhat at bay, having my balls drained fairly regularly.

Then, one night at the start of summer, I was hanging out with a couple of my best buddies, Zach and Bill, when we ran into Mary. I had actually known Mary since childhood (had a crush on her when we were kids), and her brother and I were also friends. But she had gone away to boarding school many years before, so I hadn’t seen her that much as a teenager.

She pretty much inserted herself into our trio that night, and we all ended up hanging out until very late, drinking beers and getting stoned together on her parent’s porch. She was an instant hit with all of us because she was very cool and fun to be around. It also didn’t hurt that she had grown up drop-dead gorgeous. Petite with small, elven features and raven dark hair. She had this alluring feminine confidence and sensuality about her that was very attractive. Best part about her is that she was easy going, drama free, and just generally down for whatever. Super cool chick.

From that moment on, the four of us spent a lot of our free time together and it was pretty perfect. We had a good core group to navigate many of the parties and other social gatherings that summer was full of, while also chilling on our own.

At the beginning, though it was never officially discussed, none of us guys seemed to be actively trying to fuck Mary. Nor did she seem inclined to seduce any of us, in turn. We all flirted a lot, but it truly felt more friendly than anything else. For me, even though I found her very attractive, I was honestly enjoying our group dynamic and having such an easygoing and fun friendship with a girl. Mary was delightfully low-maintenance and cool compared to most of my other female friends at the time, and her presence had a magic to it I had no interest in disrupting.

But about halfway through the summer, that unspoken agreement started to collapse when Bill decided he really liked Mary, and began to make more overt attempts to get in her pants. Thus began a somewhat frustrating but funny dynamic where Bill was always trying to move things in that direction, while Mary playfully rebuffed him.

This was actually my first time seeing a real life example of how coming on too strong as a guy can guarantee failure. Bill was a very handsome and popular guy who had always been pretty successful with the ladies. Looking back, I think had he not been trying so hard, he almost certainly could have been fucking Mary casually. She was not shy talking about her sex life and seemed to have had a lot of it away at boarding school, including multiple threesomes, anal sex, and a number of other experiences not common at 18. She had also mentioned there were a couple of guys she was casually fucking that summer as well. It seems like Bill could have definitely gotten into her rotation if he had been more cool and easygoing about it.

However, the harder he tried the slimmer his chances seemed to get. Mary started confiding in me that Bill was always trying to get her alone and clearly wanted her, but she didn’t want to hook up with him. All the while, we were still carrying on mostly as normal, hanging out a lot, drinking and smoking and partying as college-bound teenagers do.

At first I thought it was my imagination, but oblivious as I sometimes was in those days, I began to suspect Mary was starting to come onto me. There were lots of little signs at first with her being a bit flirtier, holding more eye contact and her gaze lingering longer. I would find her touching me more than necessary, and generally being more sensual and seductive around me. I remember being at a small gathering at a lake house one night and she playfully wrapped her arms around my neck and started dancing close with me. I looked into her eyes and recognized that slut sparkle I had so recently become acquainted with, and knew I was in trouble.

At this point there were only a few weeks left in summer and I was having a real crisis of conscience. On the one hand, Mary was the sister of a good friend of mine (he was out of state that summer). Also my other close friend Bill had made his intention to get with her clear, and on top of that I didn’t want to be the one to ruin our great group friendship dynamic. On the other hand, I was getting increasingly bright green lights from this very attractive and cool girl whom I had grown closer to that summer, and who was clearly no sexual prude. Hanging in the balance was my V-card that was burning a hole in my pocket.

I hadn’t made up my mind, but I was definitely starting to fantasize about Mary and I hooking up as I waited to see what might happen next.

Next came sooner than I had bargained for. Bill had a small gathering at his parents’ house one evening. As the night wore on, the crowd thinned out until it was just the four of us left standing. The atmosphere had felt very charged that night. Bill knew the clock was ticking on summer and was feeding himself and all of us more alcohol than normal, so we were all pretty faded.

We must have played never-have-I-ever or something of that sort, because I recall that the conversation had gotten pretty sexual for a bit. Mary was being even less shy than normal, and telling us a lot of her experiences in teasingly slutty detail. There was one point where we were sitting on the porch around a small fire while Mary was graphically describing a threesome she had participated in. I noticed all three of us guys were trying to subtly hide that we were all rock hard, and Bill was excitedly asking her questions about it. I remember she was wearing this short skirt and sitting in such a way that I swear she knew I could see up it. I noticed her black thong was barely containing her pussy lips, and I couldn’t keep my eyes away for long. She definitely noticed and gave me this sly smile. I wanted her bad at this point and she knew it.

At some point later, Zach and Bill went inside and left Mary and I sitting close beside each other. I don’t remember exactly how it happened, but it was as if the way she looked at me made it impossible for me to resist leaning in and kissing her. She reciprocated immediately and enthusiastically and we made out furiously as the sexual tension that had been building between us started to release. We stopped just long enough for me to check that there was no sign of Zach and Bill returning as I turned back toward her.

“I’m so happy you finally kissed me,” she purred in my ear, before locking her lips back onto mine. Our hands started desperately exploring each other. I was wearing these thin cotton shorts with no underwear, and had been pitching a massive tent since we first started making out. Her hand found it quickly and she began grasping and jerking me off through my shorts fabric while our tongues intertwined.

The sound of the porch door opening caused me to pull away quickly. Mary did the same, and it seemed neither Zach nor Bill had caught us as they sat back down.

I really wanted to avoid the awkwardness of Mary and I being caught hooking up, especially by Bill. Thus I was pointedly trying to play it cool and like nothing was up. Mary seemed less concerned about it than me, but was willing to play along, or at least have fun with it. Twice more that night, the moment we were left alone she would pounce, pulling me in for a kiss and rubbing my dick, which I had tucked up into my waistband but was sticking far up through to my abs and leaving a huge bulging tent on my t shirt that was difficult to hide. Fortunately everyone was pretty drunk and neither of the guys seemed to notice.

Meanwhile, I was rapidly losing my resistance to keep up this charade. Mary and I had made some excuse to go to the kitchen together, and within seconds she had her hand down my shorts, stroking my dick and telling she loved how big I was (I’m 7.5″ and pretty thick). I muttered something feeble about Bill clearly being into her and not wanting to get caught, at which she responded boldly that she could hook up with whoever she wanted to.

I caved and told her that we should get out of there. She thought this was a great idea, and went out onto the porch where the other guys were sitting and announced she was going home and I was going to follow her there to make sure she arrived ok. It seemed a pretty feeble reasoning, but the other two were pretty far gone and didn’t question it. Neither of us had any business driving (don’t drive drunk kids, it’s not worth it), but I was clearly thinking only with my dick and followed her in my car as she pulled away. Fortunately Mary’s place was not far from Bill’s, and it was all back roads.

As I pulled behind her into her parent’s driveway, I wasn’t sure what the plan was. I guess we were both kind of winging it. Mary stumbled out of her car barefoot as I stepped out of mine. She came up to me and we made out really sloppily as I bent down to her small height, hands groping each other in that way horny teenagers do.

“Hold on, I’ve got to pee,” she said as she steadied herself on me and slipped her thong off with one hand. “You can have these,” she giggled, pushing her underwear into my pocket. She then proceeded to squat down on the front line in her skirt and went right there.

It was beginning to dawn on me just how drunk we both were, but any thought of stopping was quickly pushed aside when she came back up and rose on her tip toes to kiss me. She popped back onto her heels and gave me this sultry smile.

“C’mon,” she said brightly, and skipped over to the back door of my car. She let herself in and slid across the back seat, gesturing me to follow. Fortunately, I had an SUV.

Mary wasted no time as I shut the door behind me. She peeled of her top, revealing a set of B cup tits with small, dark nipples, and quickly sliding off her skirt until she was fully naked.

“You gotta get naked too!” She giggled as she pulled my shirt off and gave an appreciative “Mmmm” as she ran her hands over my chest and abs before grabbing my shorts and pulling them down. As soon as my rock hard dick popped out she was grasping it, rubbing my balls, and jerking me rhythmically. I think she had some experience with uncut guys, because she didn’t seem remotely mystified by my foreskin. She seemed to generally know how it worked as she jerked me a few times with the skin forward.

Mary shifted around and brought her head towards my dick as I knew what was coming. She rolled my foreskin down and held it there as she slipped the head into her mouth and began sucking in earnest. She did not have Elise’s skills by a long shot, but she made up for it with sloppy enthusiasm. I grabbed the back of her hair and she moaned in excitement as I guided her firmly up and down my length for a few seconds before she pushed off, gasping for air,

“Come here,” she said breathily, pulling me into her as she laid back across the seat and opened her legs to wrap around me. We made out as my dick pushed against her. There had been no talk of a condom and I didn’t have one in any case. She reached down with one hand and helped guide my tip to her entrance and spread her lips. “Push!” she moaned into my ear as I shifted my weight into her. There was a lot of resistance and I was worried about hurting her, but she encouraging me to push harder until I parted her lips and the head of my dick popped into her pussy.

She was incredibly tight. I’m glad that she had clearly had a lot of sex and was clearly very wet and turned on, otherwise she probably would have had a hard time taking me. I was on full lust-filled adrenaline, and couldn’t believe I was inside a girl, completely raw, for the first time. I had fantasized a lot about what a pussy would feel like, but there was just no way to be prepared for the real thing.

As I pushed deeper into Mary, I was struck by how warm, smooth, and fucking good it felt. I knew on a visceral level that I was finally using my penis in exactly the way it was meant for, and had been missing it’s true purpose up until now. The completeness of it, being enveloped by her as I got more of my length inside her, was like sinking into a hot bath and your muscles relaxing in the most satisfying way possible, while also being incredibly hungry for more.

About 3/4 of the way in, I reached the end, pushing up against her cervix as she gasped out. I slid slowly back out until the head of my dick was just barely inside her, the entrance of her pussy gripping it with rhythmic pulses that kind of reminded me of getting head. I then pushed back in with a long, deep stroke as Mary moaned out loud in pleasure. As I went for the 3rd stroke she sat up, grapping my ass impatiently to force me harder and deeper into her.

“Fuck me!” she cried out, “Please fuck me, Steve!”

My name is not Steve. This was one of the guys she had mentioned she was also fucking. She didn’t even seem to notice. I didn’t mind, and actually thought it was kind of hot. *What a little slut* is what actually went through my head. And I have to tell you, I was into it. It gave me the push I needed to unleash the inner animal, to use her for my pleasure and fuck her without holding back. I started giving it to her hard: I began with deep, rhythmic strokes and continually increased the pace. I was surprised how natural I was at it, despite my lack of experience.

As I got faster and faster, Mary moaned louder and louder, digging her nails in hard to my back as I felt her pussy begin to tighten harder around me. A loud continuous moan turned into a kind of high-pitched exclamation until she dropped into a gasping, spasming silence as her whole body shook, and I realized she was cumming as I fucked her through her orgasm.

Thank god I was uncircumcised, because at this time the head of my dick was still extremely sensitive. So much so that the sensation bordered on being uncomfortable as I thrusted harder and faster into her. Otherwise, I don’t think I would have lasted more than a minute inside Mary. I was able to ride out her orgasm even though I did start to feel really close to losing it a few times.

I slowed down as her spasms subsided. She moved her arm up, sort of kissing and biting the back of her hand as she breathed heavily, her tits heaving up and down. She took only a moment to recover before she was wrapping her arms and legs around me again.

“Keep going! Keep fucking me!” she moaned at me, and I couldn’t help but to oblige. It couldn’t have been more than 2-3 minutes since I was first inside her. As another minute passed of me giving it to her hard and deep as she moaned louder and louder.

I began to realize the hyper sensitivity of my dick was wearing off now as I grew accustomed to the sensation, and I was in deep trouble. Without that slight uncomfortable feeling, I was getting only the pleasure now. That, combined with how hot the situation was: I was fucking a friend’s sister, a girl I had known since childhood, one I had become good friends with who another buddy desperately wanted but couldn’t have, and who was clearly a raging slut in the best way possible. I was realizing I was going to have trouble holding back as I felt all the tell-tale signs of an impending orgasm coming on very fast.

I tried to slow my pace a little but Mary wasn’t having it. She was begging me to fuck her harder and wrapping herself around me tightly. I was beginning to growl and moan myself now with pleasurable feelings growing out of control in my dick and deep down into my prostate. I was intoxicated by her and how powerful I felt making her feel this good. Something shifted in her pussy as I was bottoming out and it was like I had unlocked some extra room and was suddenly able to push into her balls deep. I tried thinking of baseball and cold showers but it was no good. I knew I was about 10-20 seconds from completely losing control.

“Fuck Mary! I blurted out, “I can’t hold it much longer…”

“Yes!” She exclaimed excitedly, her eyes lighting up as her pussy began to tighten around me. “I want you to cum. Fill me up with it!”

If this wasn’t enough, she grabbed one of my hands and shoved two fingers into her mouth where she wrapped her lips around them and sucked and tongued them. I had no idea that could feel so good and be so hot. It was over now, I had lost control and I was barreling forward towards what I knew would be a powerfully explosive orgasm. The knowledge that I was about to cum inside her was driving me wild and pushing my body to give everything to her.

Mary’s pussy was gripping around me hard and rhythmically. Whether she was doing this intentionally, or it was part of her orgasm, I couldn’t be sure. But I could feel her start to cum again as she reached her hands down below where I was slamming into her. One hand grabbed my balls and pulled and squeezed them lightly, while the other reached lower and rubbed that area between my legs. I had one final realization that she was trying to milk the cum out of me before the wave of unstoppable pleasure overtook me and I came *hard*.

“Fuck, I’m cumming!” I growled out as I pushed in to the hilt and began to unload everything I had into her. I could tell I was cumming *a lot* as I pulsed uncontrollably and shot rope after rope deep into her tight little pussy, which took it all eagerly. We both spasmed and came together as we rode out our orgasms in a feedback loop of heightening pleasure and release.

I was awhile until we both caught our breath. Mary took my hand out of her mouth and wrapped her arms once more around me, squeezing me tightly and running her hands over my back with a kind of hungry affection.

“You fucked me so good!” She whispered sultrily into my ear, and we made out for awhile, still intertwined with me deep inside her and still hard. I’d spasm from time to time and she would gasp, but she told me she couldn’t handle any more and was already going to be so sore with how big my dick was.

Eventually I slid out of her and we disentangled. She cupped her pussy in her hand and opened the door of the car, stepping out from the driveway and onto the lawn again. It’s a good thing it was the middle of the night and no cars were driving by, because she squatted down on the grass completely naked.

“Wow, you came so much!” She exclaimed as my cum dripped out of her pussy. “I can’t believe how much there is.” She giggled hard.

She peed again before hopping back in the car, where we slowly got dressed and laughed about how sexy and fun that was. We made out softly for a bit more until she said goodnight and went inside.

I got back into the driver’s seat and realized the front passenger window was cracked open a little. The whole neighborhood probably heard our loud fucking and I’m forever grateful we didn’t wake anyone up (especially her parents) to have them come interrupt us.

By mutual consent, Mary and I kept our hooking up a secret in the short time remaining that summer, but gave each other eyes and knowing looks a lot as we were hanging out with others. We had sex a handful of other times, always in each others cars late at night in different locations, since we were both staying with our parents.

I would have liked our summer fling to continue for longer, but it was soon time to depart for different colleges and that was the end of it. Without discussing it, I knew we were on the same page that under different circumstances we might have considered dating. But at the time we both wanted freedom and new experiences, and to keep a good friendship, which we still have to this day.

Later on, Mary and Bill hooked up as they went to the same college, and actually were in a relationship for awhile. I found out years later, that she and Zach ended up fucking a few times as well. So in the end, we all became Eskimo brothers and had our time with her, though never overlapping.

Mary and I would go on to live in the same distant city for awhile, so I would see her semi-regularly over the years. There was one time we discussed having sex again, but it didn’t happen and we never hooked up again. I kind of regret we didn’t have a sexual reunion, but I remember I was casually sleeping with a friend of hers at the time, and I was worried about things getting messy. All in all, it was probably for the best. I am happy to have the connection we do and to have had the best possible story of losing my virginity I could have asked for.

Source: reddit.com/r/gonewildstories/comments/wxpevy/the_one_where_i_lost_my_virginity_to_a_friends