At the time of this story, I was 30 years old and a virgin. I had never had a relationship (still haven’t actually) and also had never kissed or even held hands with a girl. This was primarily because I was a bit shy and had never really put in much effort in trying to get a girlfriend. Also, I wasn’t meeting that many people, so was never in a position where mutual interest could have led to something more.
I had just moved to a new city and country, so I was attending various meetups in order to meet some people in this new place. I met her at one such meetup. She was a 24 year old girl from Eastern Europe, also fairly new to the city. She had dark blonde hair, and was slender and very tall. I’m 6 feet tall, and she was only just a bit shorter than me. We talked for a bit throughout the evening, and before she left she came to find me to tell me something. I’m not exaggerating when I say it went something like this:
“It liked talking to you and…I thought…maybe…we could…maybe…” while looking like it was a struggle just to speak.
It was a level of shyness and awkwardness that I thought only happened in movies and TV shows. I was a bit amused and asked her if she wanted to exchange numbers, she nodded yes, and so we did. She left the meetup, and I went back to the people I had been talking to with my heart already beating a bit faster and and my cock slightly stiffening just thinking about what might happen in the future. As you can see, I wasn’t too experienced in even simple situations like exchanging numbers with a girl.
We met up several times over the next couple weeks, going on walks, going to the movies. After spending more time with her, I was quite sure that I did not see myself in a relationship with her. I mean, I found her physically attractive, but I didn’t feel anything more than just a friendship.
Finally, one weekend, she told me she wanted to come over to my apartment so I could help her with a language that she was trying to learn. I was curious to see what would happen with her at my apartment, so of course I agreed. She came over in the late afternoon, and I helped her with her work. Afterward, we continued talking about a variety of things, including relationships. She was very surprised that I had never been in a relationship. We grabbed a quick dinner and then went back to my place to watch a movie.
It had gotten a bit late, so I offered that she could stay over for the night. She got ready to sleep on the very small couch, but I told her that my bed was more than big enough for two, and if she wanted to, she could sleep there. She agreed enthusiastically. I gave her a t-shirt and old basketball shorts to sleep in. I got pretty excited when I noticed that her small tits were bra-less under the shirt.
After a few minutes in bed, she said “Can I hug you?”
I said “Sure”, so she scooted over and lay one arm over me as I was laying on my back. Now, this wasn’t even sexual at all, but because of nerves, anxiety, or whatever, my body just started shivering uncontrollably, as if I had the flu (has this happened to anyone else?). She was amused by it, but understanding, and continued to hold me as I shivered. After what seemed like 10 minutes, the shivering went away, and then she moved back to her side of the bed to fall asleep.
As you can imagine, I didn’t sleep very well that night. My mind was going all over the place, trying to process what was happening. Finally, very early in the morning, maybe 6 am, she woke up and came to me in the bed. Instead of just one arm, this time she gave me a full hug, which I returned. After several minutes like this, I decided to squeeze her a bit harder. She returned the squeeze.
I took it a step further, I gave a slight thrust with my pelvis. I wasn’t sure, but it felt like she returned the thrust. I thrust again, she thrust back. After this, I didn’t stop at a single thrust, I kept slowly thrusting into her, and she was thrusting into me. Eventually, this became more frenzied, thrusting our pelvises together as we hugged.
We continued like that, without ever saying a word, in various positions. At one point, I was laying on top of her, and my face was right above hers. Without saying anything, she lifted her head up and kissed me. It was my first kiss. I was pleasantly surprised, so I returned the kiss. And thus we continued, hugging and thrusting and kissing. At one point, she was straddling me like in a cowgirl position, and her face and neck was all flushed from excitement, so I decided to be bold and reach for her left breast. As soon as my hand touch her breast through the shirt, she reached up and grabbed my hand, and said “Sorry, I’m not read for that.” I apologized and told her that I understood, so we just continued what we were doing until the excitement died down a bit. She said she should get going, so we got out of bed, and before she left, we talked a bit about what happened. She said maybe she shouldn’t have kissed me because she thought I was bothered by it, but I assured her that I had had fun as well. I was left with a racing mind, a sore pelvic bone, and a mild case of blue balls (something which I had never felt before), which I promptly took care of.
The next weekend, we met up again at my apartment again. I again helped her with her work, but after finishing, she told that she had thought a lot about the previous weekend and that she was a bit confused as well because she only wanted serious relationships. I told her I was a bit confused about what happened as well. She asked if maybe we could try to go out as a couple for a bit to see how it felt, and I was bit tentative, but I agreed nevertheless. I don’t think my brain was doing all the thinking for me there. She stayed over a bit longer as we watched a movie, but this time, we made out for about 75% of the movie. Just before she left for the night, she let me feel up her tits (though they were covered by her shirt and bra). At first, I was grabbing for them awkwardly (that sounds a bit strange, but they were small, not that I minded one bit), so she laughed and showed me a better way. At one point, she felt my stiffening cock pressing into her and said “Sorry, but I can’t help you with that” while smiling mischievously.
After these two episodes, I felt bad because I acknowledged that I didn’t have feelings for her, it was purely physical, and the last thing I wanted to do was to lie to her to get into her pants. I decided I would tell her all this the next time I met her, which happened to be the following Tuesday night.
We met up at a popular viewpoint which offers really nice views of the city. We sat down together, with me facing the city, and her sitting sideways facing me, and straddling with me with her legs. She put one arm around me, and put her other arm under my jacket and sweater and tucked her hand into my waistband, so her fingertips were resting at the top edge of my pubes. I gasped a bit because of where her hand was, and also because her hand was cold against my skin. She asked if it was fine, and of course I said yes.
I then told her what I had feeling about her, that I don’t think I shared the same feelings for her that she did for me, and that I don’t think I was willing to have a serious relationship with her. To my surprise, she said she felt the same, and that she didn’t expect anything from me, and that she was fine with a no strings attached situation. That was fine with me, so we sat there, cuddling and occasionally making out. Finally, she started talking about how cold it was, and how cold it would be in her bed that night.
I said “So I guess you would prefer coming home with me tonight?” to which replied with “Yes!” Just before untangling her legs and standing up, she pulled her hand out of my waistband and gave my cock, which by now was hard and the tip soaked with precum, a single caress through my jeans.
We made our way back to my place, and quickly got ready for bed. I again loaned her a t-shirt and basketball shorts. As I came out of the bathroom after changing, I saw her sitting on the bed, looking at me with large eyes. I sat down next to her, and she immediately moved to embrace me. We started making out pretty heavily as my hand roamed across her back.
As we continued to make out, one of her hands reached down and started rubbing my hard cock through my shorts. I let out a soft moan, so she moved her hand further down to reach up through the opening in my shorts to finally grab and start stroking my cock with her bare hand. I was in heaven. By this time, I had moved my hands to the front of her shirt was stroking her small tits, rubbing my thumb where I imagined the nipples to be.
“Let’s talk about sex,” she whispered.
“Ok!” I said.
“How often do you masturbate?”
“Almost every day”
“Oh! That’s good. What kind of porn do you like?”
“Oh, just regular stuff, I don’t know.”
“There isn’t something you really like, like big breasts or anal?”
“I usually don’t like either of those things in porn, actually.”
“Ok, well I like all sex, even anal,” she said.
With that, she pulled my t-shirt off. She got on top of me to straddle my stomach, and seeing how my shirt was off, I thought hers should come off too. I began pulling it up, and I got a glimpse of two dark nipples before she stopped me, pulled the shirt back down and said, “I’m sorry, but I have bad skin. Don’t worry, it’s not contagious or anything.” I assured that it was fine and it didn’t bother me, so I reached for her shirt again, and this time she didn’t stop me from lifting it off.
In front of me was my first pair of breasts. As I said earlier, they were fairly small, but with two perfectly sized, dark nipples. She told me her nipples were sensitive, so I used my thumb to gently flick them, and brought her chest closer to my face so I could lick each one as they hardened up.
It was at this time that I asked if I could feel her pussy. She said yes, so I slid my hand down her flat stomach, under her shorts, and into her panties. As my hand moved down, I could feel the scratchiness of her recently shaved pubic stubble and an incredible heat. As I reached her clit, for some reason, I yanked my hand out. She giggled and reached for my shorts and slid them off, along with my boxers, leaving me completely naked in front of her.
She wasted no time in bringing her mouth to my cock, licking it, sucking it. Sometimes her tongue would hit a certain spot which left me throwing my head back and gasping. I learned later that she was fascinated by the shape of my cock. I’m not sure why, it’s about average length, maybe a little thicker in some parts, but she would always ask me to show her how I masturbate because she thought it affected the shape of my cock when it was hard. Additionally, I wasn’t trimming at the time, so she would sometimes grab my pubes in her fist and say “I really like this part!”
She still had on some clothes, so naturally, they needed to come off. I slid off her basketball shorts, exposing her beige panties that were adorned with peace symbols. I too removed these, exposing her shaved pussy to me. I was transfixed and almost afraid to touch it. I finally reached out, and felt along her pussy lips with my finger. I could feel that she was absolutely soaking wet without even inserting a finger in her pussy. “Wow! You are so wet!” She laughed, and showed me how I could stick a fingertip in to get it wet and then stroke it along her pussy lips and mound. I played with her pussy a bit before realizing that I really liked sticking my finger (or two) inside her pussy. I had always wondered what a pussy felt like, and it really satisfied all my wildest expectations! I started using the “come here” motion with my fingers while I was inside her. She really enjoyed that, as I heard the first soft moan escape from her lips. Upon hearing her moan, I doubled down on my fingering. This is what I had been fantasizing about for so many years.
“Grab my ass”, she said. “I really like it when you squeeze my ass.” I would later learn that she could cum only with me playing with and squeezing her ass.
So there I was, one hand pumping my fingers in and out of her soaking pussy, with the other hand grabbing one ass cheek, then the other, then both at the same time. She was moaning more now, her eyes were closed, and had stopped stroking my cock as if to focus on the pleasure.
“If you keep doing that, I will cum.” I didn’t stop. Eventually her moaning quickened, then stopped, and she began lightly thrashing around on the bed. I kept fingering throughout, until she was able to recover. She opened her eyes, looked at me quite fiercely, then grabbed my cock and started stroking harder than before. She alternated between stroking and licking my tip. At one point, she guided my cock between her legs. I involuntarily flinched and pulled back a bit, but she said “Don’t worry, not inside”. She squeezed her slim thighs around my cock and I fucked her thighs for a bit. Throughout all this playing around, she would come up for air and check on me, and would laugh because I think I had a bit of a frantic look on my face and I could feel my heart threatening to beat its way out of my chest. I tried to relax, but how could I? I was there with her ass in my hands, her juice on my fingers, and my cock in her hands and mouth.
“I want to cum,” I said as I really couldn’t take it anymore.
“Are you sure?” she replied.
“Yes, I need to cum.”
Unfortunately, I had a bit of a problem. Because of nerves or anxiety, or whatever, my cock wasn’t as hard as it could be, and even with all the stroking and licking and excitement, I hadn’t felt close to cumming yet. Nevertheless, she increased her pace of stroking. She would also interrupt her stroking every 5 seconds to lick my head, which honestly, I think would interrupt any orgasm buildup I had. Eventually, I told her that I didn’t think I could cum that way. She understood, so I got up to straddle her chest and I grabbed my cock with my own hand and started stroking off in front of her face. My cock responded better to my hand, and I soon felt the familiar flame light and my balls beginning to tighten.
“I’m going to cum,” I gasped out.
The flame ignited, and as the pleasure spread out from my groin, she closed her mouth around the tip of my cock. I couldn’t see my cum spurting into her mouth (which I later realized disappointed me, since seeing my cum on or in someone’s body really excites me), but the pulses in my shaft were intense, as it was my first orgasm in front of someone else, and obviously the first time unloading in someone’s mouth. After my balls had emptied and my cock stopped pulsating in my hand, the tension left my body, and I got off her so we could both get cleaned up and ready for bed. I’m not sure if I even was able to speak, so I’m not sure if any words were exchanged.
We lay in bed together, trying and failing to fall asleep. I was still processing what had happened, the only thing I knew for sure was that I really liked it. I got up to use the bathroom, and when I returned to bed, she came to me and through an arm and a leg over me. My cock quickly started getting hard against her thigh.
“I’m still hard for you,” I told her.
“Mmm, yes.”
I slid my hand down her back, across her ass, and started feeling her pussy through her shorts. Her wetness was making the fabric damp, so I exclaimed “You are so wet!”
“Of course!” she replied while giggling. By now her hand had found my cock and was stroking it gently. I gasped and squirmed a few times as she reached for my too-sensitive balls. “I really like how wet you are too!” she said, talking about the precum that had been oozing out of my cock for pretty much the entire night.
“I want you so fucking bad,” I whispered to her as my mouth nuzzled under her ear. We both slid our shorts halfway down to get easier access and strained and flexed against each other as she pumped my cock and I slid my fingers in and out of her wet pussy.
“I can see that you like to talk dirty! That’s good!” she said. After a few minutes of pumping and grinding and moaning and gasping together, she finally said the words that I had been waiting for: “I want to fuck you.”
I replied with “I want to fuck you too” and followed it up with “So I actually have some condoms, should I get them?”
“Haha why do you have condoms?”
“Well I didn’t think I would remain a virgin forever!”
With that, I got out of bed to get the condoms. I thought it was really hot how she rushed to rip off her shorts and shirt to get completely naked for me in preparation. I grabbed a condom, and being nervous and all, double checked the expiration date and made sure there were no holes in the packaging. My cock again was not fully cooperating, but it was hard enough on which to unroll the condom.
She was laying on her back on the bed, so I jumped on the bed in between her legs. She licked her fingers and rubbed her pussy to get ready, which amused me because I had seen that in porn, and wasn’t sure people actually did that, and also because her pussy and lips were already so drenched.
I positioned my cock at the entrance to her pussy, and after some awkward motions on the bed, was able to line up the tip. I thrust forward, met some resistance, then thrust harder to push through. She gasped as I sunk in all the way, and that was it, I was no longer a virgin. I began thrusting slowly and to be honest, probably not very well, in and out of her. I reached one hand down to play with her clit, though she had told me earlier that her clit was not that sensitive. As I continued thrusting, I was just trying to freeze the image in my mind: my condom-covered cock sliding in and out of her soaking, shaved pussy, the nipples on her small tits only barely moving up and down with each thrust, and her face looking toward side, with her eyes closed and soft moans escaping her mouth. She even started quietly repeating my name.
As you can imagine, my erection and anxiety problems were handicapping me a bit. I pulled out of her, to attempt to stroke a bit more hardness in my cock. The condom was absolutely soaking wet after being inside her. I also asked her to try a different position, so she got out of the bed, and bent over the edge so I could take her from behind. My cock slid in much more easily this time and I started pumping her pussy as I reached one hand forward to play with her nipples. My other hand squeezed her ass as her moaning got louder. In between her moans, she told me how much she liked the feeling of my balls making contact against her clit.
Frustrated that I was not as hard, we switched back to missionary, but I still wasn’t able to perform like the sex expert that I wanted so hard to be. I tried quicker thrusts, slower thrusts, but I really was not getting much sensation on my cock. Don’t get me wrong, I was still really enjoying the moment, but the frustration was just too much. I told her that it wasn’t working very well, and apologized that I wasn’t doing a great job in pleasuring her. She tried to calm me down and said it was normal. Finally, I took off the condom, straddled her chest like before, and once again emptied my balls into her mouth for the second time. I don’t think she came while my cock was thrusting in and out of her, but she did tell me she enjoyed it.
We then settled back into bed, this time with the intention of sleeping. There was no chance I could get much sleep that night, so I just lay there, trying to play back everything that had happened. After what seemed like an eternity, dawn rolled around, and she began stirring on her side of the bed. I reached out with one arm, she turned to face me, and then we met in the middle to hug again. One thing led to another, and soon her hand was on my shaft, my fingers were rubbing her pussy, and my other hand roamed around her small breasts. She came with my fingers inside her, and I jacked myself off in her mouth like the last two times. However, this time, she made as if to squeeze my cock with her hand as my orgasm was pulsating through it, so I removed my hand as my cum was flowing out. Her hand ended up not getting in there in time, so I was left with a bit of a ruined orgasm. We went to the bathroom together to clean up, and I felt that I wasn’t completely spent yet, so I said “Wait, I have some more.” We watched ourselves in the mirror as I jacked my very tired cock off against her ass. My fourth orgasm brought the last few drops of cum out of my spent balls on the smooth curve of her right cheek, and I almost collapsed against the wall, exhausted physically and mentally.
“I can’t believe we had sex,” I told her. “I can,” she replied while smiling, apparently not too tired.
Anyway, we cleaned up, and parted ways since I had to go off to work. I was basically a zombie in the office, not able to concentrate because of my fatigue and because of what I had experienced during the night.
We ended up hooking up for 3 or so months, I think we had sex a total of 7 times. Yes, I was finally able to cum from one of her handjobs. When I would start cumming, she would paralyze me by slowly squeezing the head of my cock. Also, I was eventually able to cum while fucking her (with a condom of course). She ended up moving away, but we still kept in touch irregularly for a bit, but my last two messages to her have gone without reply. I figure she might be trying to forget about me since I always thought she had more feelings for me than I did for her, and despite her insistence that our casual sex was great, she was frustrated that she couldn’t have something more with me. I was always very honest with her because the last thing I wanted to do was to hurt her and lie to her just for sex. All this happened less than two years ago, and I haven’t had any other sexual experiences with anyone else. I still occasionally think about these memories when masturbating, and also fantasize about what I would do with her if one day we were to meet up again.
Source: reddit.com/r/gonewildstories/comments/abj88b/mf_losing_my_virginity_late_and_finding_out_that
Beautiful story. Also helps to show many people that they aren’t alone in their sexual experience not being a mind-blowing torrent of smooth pleasure every single time. These things are worth it but need work, for most people, most of the time.
I had this shivering thing too :D
Back when I started making out with girls (one at a time of course), my legs would not stop trembling :D
And compared to my first time, you hit the jackpot, trust me :D
Your story is probably one of the best I’ve read on Reddit for a long time mate. Kudos to you for sharing your experiences and fears, it sounds like you really spoke from the heart here. All the best for 2019 my friend.
I have the shivering problem, frustrating some times :(
Thx for that story, glad to know, i’m not alone in my problem, 26 years old, and still virgin…
Your story is great, thanks for sharing! All the things you went through (the shaking, difficulty staying hard, not being able to cum with her) are all pretty normal.. Most people don’t talk about it though, which is tragic. First time I got to touch / kiss bare tits I was shaking uncontrollably, she kept asking if I was OK.
Really well written! Felt like I was there with you ?
I think we mystify sex sometimes by expecting that is always going to be something great like out of a movie.
If we treated it like any other bodily function and relaxed about it, it would make things so much easier. I know that’s easier said than done sometimes.
Well done for giving such an honest perspective on your experiences that have obviously stayed with you – and for good reason.
Remember that many women, whether that have experience or not, value and respond to a respectful man, such as you seem to be. I hope 2019 is the year you find more opportunities like this.
I’m an (almost) 30 year-old virgin with a lot of social anxiety and insecurity and your story fills me with hope. Thank you.