First Man Sex

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Love



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Dear 17




"Five minutes in, we heard a voice say, 'What are you guys doing?!'"
No matter how old you are or what the circumstances are, having sex for the first time can feel like a huge deal. Everyone's experiences are different. Below, 18 guys get real about the first time they had sex — who they did it with, how it happened, and how they felt afterward.
1. "I had just turned 17 and my girlfriend and I had been dating for a few months when we decided it was the right time. After waiting two or three nights out of anxiety, we were finally able to share the experience. We waited for her parents to go to bed, and after what seemed like hours, they did. We fumbled around with the condom in the dark, but eventually realized it would be easier with the lights on. " — Jay, 18
2. "I was 18 and in my first semester of college. The girl I lost my virginity with was a good friend of mine. One night, we were both coming back from a party. In the Uber home, we started flirting and making out. When we got back to her dorm, we went at it. Five minutes in, we heard a voice say, 'What are you guys doing?!' It was her roommate — sitting upright, staring at us from her bed. We were so busy hooking up that we forgot to check if she was asleep." — Jake, 19
3. "We had been hooking up and hanging out for about three weeks when I was 21. We got really serious, really quickly, basically spending all our weekends and some weekday time together. She was staying at my family's house for the weekend — the first time either of us had met another's parents — and when we realized everyone had left for a few hours one morning, we gave sex a shot. We didn't really know what we were doing, but it wasn't awkward at all because we trusted each other a lot. We laughed when we decided to leave the bedroom doors wide open, since it was important to hear people coming back. At the time, I was pretty pumped. And sweaty. Two days later, we became official." — Landon, 22
4. "I met a girl off of Tinder. On our third date, we were watching movies at her place and getting along well. We just cuddled, kissed, and went slowly from there. I never told her it was my first time because of male stereotypes — I didn't want to seem inexperienced. I thought telling girls that I had never had sex would hurt my chances. I was nervous and excited at the same time, and it didn't last very long. She might have known that I was a virgin (or thought I was bad)." — Isaiah, 20
5. "I lost my virginity when I was 18 years old. As a guy, you feel a certain pressure to lose your virginity, but I still wanted my first time to be special. She was a junior in college and I was freshman. We met when she started hitting on me at a diner after a party. We started hooking up every weekend. Three weeks later, we came back to my room and things were different. Neither of us planned to have sex, but it happened. It was good, but I was so nervous, I didn't truly enjoy it. Afterwards, she told me I was amazing. Although I didn't realize my romantic dream, I didn't and still don't care. We continued hooking up for the next few months until one day she told me she was getting back together with her ex-boyfriend. To this day, I still haven't told her that she took my virginity." — Tyler, 21
6. "We were both 13. In retrospect, the entire situation was stupid. I was just a funny kid who used to be ugly; she was the hot girl that everyone wanted. I made her laugh and she thought I was cute, so we started dating. A month later, we decided to have sex. I wasn't really ready, but I just went with it. I had no idea where to put it. It felt amazing, but I regret the timing, the girl, and not using a condom." — Jon, 20
7. "It was the first week of classes during my freshman year of college, and I had been interested in a girl in my dorm since orientation. We had already been making out semi-regularly. Our make-out session was more intense than usual, so I asked if she wanted to have sex, and she nodded. If I'm being honest, I had a hard time getting started, but she was patient and helped guide me through it. I was afraid the entire time that she wasn't enjoying herself, and to make it worse, I finished very quickly. Looking back on it, I wish that I had waited until I was more certain that I was actually interested in her. A lot of my relationship with her beforehand was me thinking about losing my virginity, which certainly didn't help." — Caleb, 20
8. "I was visiting my girlfriend in college my freshman year. We had been dating for four years. It hurt for her at first. I wish it didn't. But we did what we could — we were comfortable with each other, so we were both patient. I think it was a better experience for me than it was for her." — Xander, 20
9. "I was 16 and had been in a committed relationship with the same girl for nearly two years. We had spoken about it for months. Finally, it happened one night in her bedroom when her parents were out. We made sure to use a condom. Even though I'm no longer with her, I have no regrets about it because at the time, it was right. I do, however, wish we hadn't built it up to be something that it really isn't and wish we hadn't treated it as a massive milestone." — Jack, 19
10. "I was 17 and with my girlfriend of four and a half years. It was the first time for both of us. It was after school on a Friday. We made plans to meet at her parents' apartment in the city. When I got there, the lights were dimmed, candles were lit, and she was in lingerie. She told me she wanted it to be special for the both of us. The experience was amazing, and there's never going to be another time like it. I was with the person I loved the most and couldn't have asked for it to be any better." — Matt, 19
11. "I lost it to my girlfriend when I was 18. We were together for a year or two and I loved her. At the time, I was nervous — like, what if I'm not big enough or what if I finish too quickly? But I enjoyed the experience. It was a rush of emotions." — Danny, 19
12. "I was 14 and my girlfriend was 15. We had been dating for about four months. After kind of a lot of convincing on my part, she agreed to have sex. At the time, I was thrilled. It felt almost as good as I expected it to. A bit awkward, sure, but worth it. I definitely have regrets now, though. She wasn't ready for it and it put a permanent stain on our relationship, which went on to last three years. I will always regret not waiting until she felt more comfortable. " — James, 18
13. "I was 17. We were working on a summer play together, and there was definitely some will-they-or-won't-they chemistry between us. We hung out a few times, and eventually, the subject of sex came up in conversation. I said that I was a virgin. She said she was fine with that, even though she wasn't a virgin. We actually had sex during her period, but I didn't really mind it. I was pretty happy afterward (as most guys are), but I wasn't going around boasting or anything. Our relationship eventually turned rocky — pretty typical for a high school relationship — but I'd like to think we're friends now. I try to keep in touch." — Jack, 22
14. "It's awkward because it's a different experience than anything in your life up until that point. It's a fairly simple concept, but when it's your first time, everything is difficult. I was 20. I was in a long-distance relationship with a girl I hadn't actually met in person up until that point. We didn't really know each other physically, and that probably contributed to the awkwardness. I don't have any regrets, but it could have turned out better. I could tell she was getting frustrated with how I was performing, even though I told her it was my first time. I was pretty nervous." — Kyle, 21
15. "I was 15. There was a girl in one or two of my classes, but she wasn't my girlfriend. We were basically strangers. Hooking up with her felt great because I could talk about it with my friends and feel good about myself and feel like the 'cool' one. But it was super awkward, and if I could do it all over again, I certainly would have waited a bit longer — at least to be with someone I really liked." — Louis, 22
16. "I was dating this girl for a few months when I was 13. She was great — funny but shy, cool but aloof, and she liked all the same music I did. One night, when it was pouring rain, she came over. She couldn't get a ride, so she walked three miles. That made me think maybe she wanted to have sex, which was absolutely terrifying. We had never done that before. We're both shaking — her from the freezing New England rain, me from pure fear. I'm pretty sure I used some stupid line, like, 'We should get you out of those wet clothes' or 'Let's warm you up, babe.' She handed me a condom, and neither of us could figure out how to put it on, so I called my more experienced friend and had him talk me through it. Eventually, I got it on. I came immediately. It was so brief, I honestly still felt like a virgin. A few weeks later, we had sex again for a more respectable amount of time. I remember she said, 'OK, now I feel like I've had sex.'" — Ari, 16
17. "I was 17. I had hooked up a couple times with a girl who was a year older than I was. She asked me to pick her up at a party. I didn't really know what her intentions were, but after she got in the car, she told me to park at a nearby park. We got in the backseat of the car and then things just escalated pretty quickly from there. I was happy to get it over with, especially since a couple of my friends had already lost their virginity. My only regret is that I didn't use a condom." — Drew, 19
18. "I had met a girl online and hung out with her once before we decided to have sex. I was so excited to finally lose my virginity. I was 18 at the time. I put on a condom and tried to stick it in, but a few seconds later, she was in pain. I pulled out, got dressed, and hurried out. I felt so embarrassed on the way home. I traveled three hours round trip, was there for 15 minutes, and we didn't even fully do it. To this day, I still greatly regret losing it in that way. I haven't talked to her since." — Reid, 20

Forgiving myself for being a sexual person
It had been just a few weeks since my husband had told me that if I needed to see other men to fulfill my sexual needs then he was fine with it.
Since then, my mind had run amok with the idea of seducing and taking a strange man to bed and having sex with him for nothing more than my own sexual pleasure. This was something that I’d never done in my entire life, all of my previous sexual relationships had been substandard and my needs were always left secondary to my partner’s.
Just thinking about the fun that I could potentially get up to was giving me plenty of mental stimulation and I found myself breaking away during the day to find a private place to masturbate. I’m not ashamed to say that this was happening two or three times a day.
One day shortly after the conversation, I was in a spin class and this young, 20something male instructor at the front of the class was glistening with sweat as he barked out encouragement and orders at us. I found myself riding and thinking about what it would be like to take him into a meditation room, lower his shorts and just ride him instead of this stupid cycle.
I spent so much time fantasizing about him that I found myself grinding into the seat of the spin bike while I rode. I could hear him yelling at us to get up out of the saddle but I was lost in the pleasure of using the seat to make myself orgasm, right in the middle of the class.
As my orgasm hit, I let out a help, dropped my head over the handlebars and rode faster. The pumping action of my legs on the pedals rhythmically grinding my clitoris onto the saddle seat was spectacular.
I was panting and moaning, covered in a full-body sweat. As the orgasm subsided, my head was spinning and I took a long drink from my water bottle trying to collect myself.
The class ended and as I was wiping down the seat of not just sweat, but any moisture that I’d released, the gorgeous young instructor walked past, put his hand on the small of my back and said, “You really left everything out there, that was great.”
I don’t think he knew that I’d made myself cum with the bike seat, but I didn’t care. I made my way into the shower, closed the shower stall door, and as the warm water cascaded over me, I masturbated feverishly thinking about him. I made myself cum twice in the shower before getting changed and heading back to the office.
As I made my way back to the office, there was a spring in my step, even if my legs were incredibly tired from all of the frantic pedaling I’d just done at the gym. Inside I was smiling as I thought about how fit I’d be if I went to that spin class several times a week.
The thing is, those sexy young gym instructors with their slender bodies and tight muscles were not really the kind of thing that I found physically attractive. Don’t get me wrong, I appreciate the beauty of that well-toned and looked after male form as much as the next warm-blooded woman, but when I closed my eyes and pleasured myself, that’s not what I thought about.
Oddly enough, my husband’s body shape was more aligned to what I found sexy in a man.
Jamie, my husband, was 6'2" and 225lbs before his injury. Since then he’s lost a bit of weight, but I’ve always been physically attracted to larger-sized men.
That’s probably a bit strange considering that I’m just 5'6" and 140lbs. I used to weigh a bit more, but since my husband’s injury, I’ve spent a lot of time at the gym just to relieve some stress and my overall fitness levels have improved dramatically.
So, yeah. I’m a smaller sized woman who loves really large men and when I’m pleasuring myself, that’s the type of guy I dream about.
I’d spent probably two months after my husband told me to find other men to satisfy me, just sitting on the fence and pretending like this was something I was totally into, but the truth was, I was scared.
One evening, I was downstairs on our sofa, Netflix streaming some stupid show that I wasn’t watching, and I had my hand down my pants while laying under a blanket. The kids were fast asleep and Jamie had gone to bed, but still, the blanket provided me with a bit of modesty.
Considering that he was still walking with a cane, he’d managed to sneak up behind me and catch me in the act of pleasuring myself. I was so engrossed in what I was doing that I had tuned out everything because normally, with his limited mobility, it was rare for him to go to bed and then get up and come downstairs.
He looked at me and then stared straight ahead, “I’m sorry. I didn’t know that you were busy, I just needed a drink.”
I whipped my hand out, looked around for somewhere to wipe it, chose the blanket, and then chased after him.
“Jamie, I’m sorry, I thought I was alone and that you’d gone to sleep.”
I didn’t know why I was apologizing to him. I was a grown woman in the midst of an imposed sexual drought and I had every right to pleasure myself in the privacy of my own home, but the look on his face told me that he was still taking it personally that he was not able to satisfy his wife the way he felt he probably wanted to.
He came over, leaned down and kissed my forehead, “You don’t have to apologize, Poppet. Remember what I said before, you need to have your needs met and I understand that.”
I stood there in the kitchen, staring at my feet as he slowly made his way back up the stairs. I felt embarrassed and ashamed by my lack of discretion.
Heading towards the fridge, I grabbed a glass and poured myself an enormous amount of white wine and fell into one of our dining chairs staring at the small beads of stray wine that missed the glass as I poured.
I’d made my mind up two months earlier when Jamie first suggested this arrangement that I would do it, but for some reason, I couldn’t bring myself to take it further. I wanted to be with a man again, but I just lacked the confidence to make that happen.
Going online or using something like Tinder seemed so seedy and desperate, and while that described my situation, I didn’t want to feel that way.
I finished off the remainder of the bottle of wine and somehow managed to make my way to bed, although I had no memory of any part of that.
Three weeks later, I was in Melbourne for a conference. It was the first time that I’d been away from the girls and Jamie overnight since the accident. I’d considered flying into Melbourne in the morning, flying back to Sydney that evening, and then coming back to Melbourne the next morning for the final day.
My mother laughed at me when I suggested it to her.
“Betty, you’re crazy. Jamie can look after the girls and himself for one night. This seems more about you being afraid to be away.”
My mother was an amazing lawyer because she had incredible insight into how people felt aside from what they were saying. I learned at an early age not to try and hide things from her because she always knew the truth, so we ended up developing this kind of close relationship where she was my confidant from the age of 15.
She was the only person who knew about “the offer” that Jamie had made and she was so clinical in her understanding of the situation. From the moment I told her, her view was that I needed to do what felt right, but make sure that it was purely unemotional and just a physical outlet.
“I suppose, Mom, I think an opportunity might present itself that I’m not going to be able to say ‘no’ to and that I’ll end up regretting it.”
“Betty, you’re living part of your life filled with regret now. You’ll do whatever you do and then you’ll deal with the fallout later. If you do nothing, you’ll eventually just become resentful of everything and you’ll have even more regrets.
https://www.seventeen.com/love/a42304/guys-first-time-having-sex/
https://medium.com/sexual-tendencies/my-first-time-with-another-man-3f43223446a
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