I lost my virginity just before New Years. As you can tell from my age, I am a late bloomer, and my virginity has always been a sensitive subject for me.
I would always avoid talking about girls with my family and long-time friends, while I would lie to my more recent friends, saying that I did have success with girls, but no interest in a relationship. I have had a female friend (let’s call her Natalie) for the past two years. I am closer to her than I ever was to anyone else. She’s a good, non-judgmental person to talk to about anything, but I was still very hesitant to reveal my secret to her. I told Natalie several times that I was hiding a big secret from her, but I promised to tell her eventually. I did eventually want to tell her…but AFTER I’d solved all my girl problems. However, fate had other plans. I had Natalie over my place, where she was spilling a big secret of her own: she was considering leaving her husband for a guy who lived across the ocean. After talking about her internal conflict, the subject changed from her secret to mine. At first, I’d told her the same thing I’d been telling her all along: that I wasn’t ready to let the cat out of the bag yet, but that I would eventually do so. However, Natalie insisted that fair’s fair; she had told me her big secret, so I should tell her mine. Half of me had already wanted her to guess the secret, and Natalie HAD confided something monumental in me, so I caved. I started by apologizing to Natalie, telling her that I’d lied in many of our heart-to-hearts. Then, since I saw a significant chance that I’d lose Natalie as a friend, I told her what a great friend she’d been.
And then I told her. That I was a virgin. That I wasn’t really single by choice. That my dad had never taught me how to be a man. That I had become very religious in college, and chosen a group of friends who were the same way, to avoid the judgment from my circle of friends. That most of those friends are married by now, while I have only managed to be rejected and have my heart broken over and over again. How I’d been studying pickup artistry and hired dating coaches over the past 2+ years in a bid to improve my situation. And how I’d gone to great lengths to hide my efforts from my dad (who would probably think I’m wasting my time) and my mom (a semi-radical feminist who would probably think my way of dealing with my virginity is degrading to women).
“It sounds like you’re ashamed of it,” said Natalie after I’d finished. “I am ashamed,” I said. “You see that my coat’s still off and I’m still sitting here,” said Natalie. “I have some questions for you, and I’m hoping you can be honest.” “Sure,” I said. “Are you waiting for someone special to lose your virginity to?” she asked. “Not really,” I replied. “Do you have protection for when girls come over?” Natalie continued. “Yes,” I said. It was mostly wishful thinking at that point, but I’d bought a box of condoms, keeping several in my room and several in the glove compartment in my car, so I would be protected when (and if) the moment would come. The next question was a test of my will to answer honestly: “Before you knew I was married, would I have been a girl who you’d consider hooking up with?” “Yeah, it was definitely on my mind,” I responded. It was true: Natalie is very pretty. However, because of her being married and us being friends for so long, I hadn’t really thought about her that way for a long time. I should have been able to connect the dots by now, but I didn’t, not even after the next question: “Would you consider losing it to a friend?” “That’s weird,” I said, my face contorting. “Really?” pressed Natalie. “Because we could do it just so you can get over this. We’ll use protection, and we can keep it our secret.” “I dunno…” I answered. “I really don’t want to lose your friendship…you ARE the one friend I don’t want to lose…” “But what if you knew you WOULDN’T lose me as a friend?” She had me there. I could only say, “Well…” “Come on,” she said. “Do you want to get this over with for 2014? Or do you want to wait for 2015?” “There are only a couple days left in 2014,” I said, relieved for something of this nature to say. “I know,” said Natalie impatiently.
“Do you want to get it over with or not?” I didn’t say anything. I did want to lose my virginity ASAP, but the thought of losing it to a friend still wasn’t sitting well with me. On the other hand, though, Natalie was making me a generous offer to take away my biggest stigma right then and there; no waiting for another girl to come along, and a guarantee that the girl who would be my first would be attractive. I just sat there, torn between my two instincts… “Come on,” said Natalie, taking my hand and leading me into the bedroom. That was all the persuasion I needed. I followed nervously; was this actually happening? We got to the edge of the bed, and Natalie grabbed the bottom of her shirt. “Hey,” I said, “before we start…we WILL still be friends after this, right?” “Yeah,” she said. “Thanks very much for this,” I said, giving her a big hug. “So where’s the protection?” she asked after we broke off the hug. I held up a condom in response, sitting down on the bed as I did so. Natalie took off her shirt, jumped onto the middle of the bed, lay down facing me, and slowly pulled down her bottoms. I almost froze again at the sight before remembering that I had something to do too. I lay down next to Natalie, pulling my pants down to reveal my half-hard penis. I wanted to get completely hard before starting, but my dick wouldn’t get any harder.
“Here,” said Natalie, “let me help you a little.” She reached down, giving me a few strokes. Still, though, I couldn’t get fully hard. Damn it. Seeing that this was all that would happen, I gave up and put the condom on right then. I turned toward Natalie, still looking for something to get me harder. My eyes fell on her breasts, now only covered by her bra and tank top. “May I…?” I asked, holding my hand over her chest, unsure how to ask something of this nature. She didn’t move away or say no, though, so I slowly lowered my hand, rubbing one breast, then the other. After I had felt her bosoms, Natalie got up, straddling my cock. Slowly, she lowered herself onto it. I tried to be stoic on the outside, but inside, I was wondering: is this really what it feels like to have your cock inside a pussy? I didn’t really feel much; was it just because of nerves?
Did Natalie just have a loose vagina? (She already gave birth to three kids.) Had I destroyed the sensation in my penis from years of jerking off to porn? Was it some combination of the three?
Whatever the reason, Natalie started moving up and down my shaft, moaning “Your dick is inside me” on the first few pumps. After a few minutes, she said, “Let’s try something else.” She lay facedown on the the bed, legs apart. Taking my cue, I positioned myself behind her, and inserted my penis into her again. Excited at the prospect of being the one in control, I started thrusting like a madman. After pounding away for a few more minutes, I heard Natalie moan, “You wanna cum inside me?” I could only grunt in response, but boy, did I want to! However, we went for another minute or so, and…no juice. “Damn…” I gasped after realizing it wasn’t happening.
“What’s wrong with me?” “You’re rushing,” said Natalie patiently. “Just slow down….” We changed positions again, this time with Natalie on top again. This time, I was bolder, grabbing her ass as she moved up and down. A couple of minutes into this, she pulled down her bra and tank top, and I grabbed her tits. After a few more minutes, we switched to missionary, and she tried to make me cum again. Still, though, I just couldn’t finish. “That thing you have on isn’t helping,” said Natalie. We disconnected our bodies, and she leaned over me, pulling off the condom. My worries about making her pregnant were completely eclipsed by excitement.
As we came back together, Natalie said, “I’m glad you told me; this is fun!” We started going again, and I got bolder still. I rubbed Natalie’s face, hair, and torso all over. I stuck a finger in her mouth. I sucked on her boobs. I rubbed her clit hard. I even suggested new positions to try. But even without the condom in the way, I still couldn’t finish. Natalie told me a couple more times that I was rushing, and a few times, she told me that I was nervous. A few times, she even said, “Nothing’s wrong, it’s okay.” So we kept going. And going. And going. Until suddenly…. Natalie’s phone rang, interrupting our little session. Natalie ran to get it. It was her husband, demanding to know why she hadn’t come home that night. My jaw dropped when she told me the time: it was well after 6 in the morning! Hurriedly, she ran into the bathroom to fix herself up.
After she came out, I asked Natalie my two big questions: how was I for my first time, and what did she like and dislike? To my relief, she said I was really good for my first time; I’d lasted longer than she’d thought possible. She said I could definitely get away with pretending to be more experienced. She only brought up my failure to finish as something that needed to be fixed, but told me it wasn’t the biggest deal in the world. As she left, I said quietly, “Thanks…”
So far, in spite of everything, it doesn’t feel really different now that I’m finally not a virgin anymore. It doesn’t even seem completely real that I lost my virginity. But so far, Natalie and I are still the best of friends. And to have a friend who did what Natalie did for me…well…I’m grateful beyond words for that. And as for another girl to get sexual with…well, I’m ready now in every sense of the word.
- Name: Andrew
- Gender: Male
- Age of Virginity Loss: 26
- Current Age: 26
- How would you categorize your story?: Friend
- Country: USA