tagFirst TimeLosing My Virginity at 20

Losing My Virginity at 20


Losing my virginity at 22 to a 46-year-old man I met online (100% True)

I was never really interested in sex while in High School. Certain things were occurring in my life at that time that really kind of pushed it from my mind. After leaving my home to attend college all that began to change. I began having recurring fantasies about losing my virginity to a much older man. I’ve always found them much more attractive, not to mention he would be much more experienced than any guy I would ever find my own age. There is nothing hotter than knowing the man you’re fucking has known how to please a woman since before you were even born. My fantasy to have an older man to take my virginity (or rather for me to give him) was really starting to keep me aroused 24/7. There were plenty of guys around, but where to find an older man who could be discreet was giving me a little trouble.

I decided to go online and post an ad on an adult personals website asking for a man that would be willing to teach me everything I wanted to know about sex, someone who would let me live out every fantasy I ever had (and some I had yet to think of.) My only requirement: he must be VERY experienced, and between his mid 30s to late 40s. I never really thought that I would ever answer anyone who wrote me. It was a kind of trial for myself, just how far would I be willing to take this? Not to far…or so I thought…until Greg emailed me! I had received dozens of emails, from dozens of men, all claiming to be up to the challenge, if only I’d email back they said, I could have the most incredible first time they could offer. Greg’s email stuck out for a single reason: he said I sounded great, but “just too good to be true.” In my mind, what he had essentially just done, was called me a liar! That was all it took, I emailed him back immediately stating that I was completely serious about my offer, and I certainly was a virgin. This “I’ll show him” mentality had me ready to meet this man.

We began exchanging emails and though I did not really know him I already felt quite as ease with him. We decided to meet. I told him to meet me at a park by my house and he agreed. As the time grew closer to our meeting I had so may thoughts and emotions running through my head. I was excited, I was terrified, I was anxious all mixed in one. Those little nagging thoughts came back into my head as I walked to the park “What am I doing?” “I can’t believe I’m about to do what I am!” As I entered the park I saw an SUV begin driving towards me and it slowly pulled up beside me. I opened the car door and couldn’t believe my luck. At 46 he was tan, built, well dressed, and very good looking. He smiled and said “Hi” and it was all I could do not to fall over right there. I must say though I was still quite nervous at this point. I crawled into his SUV and shook his hand, never once looking him in the eye. We drove around a bit and talked, to get better acquainted and eventually ended up at the Holiday Inn. He went in and paid for a room while I waited outside. I told him to go ahead of me and I’d be up in a second. This was the moment of truth. If I stepped on the elevator I was definitely going to give this man my virginity, if not, I was going to turn around and go home losing that one recurring dream I had been fantasizing about for so long. I pushed the up arrow, the door opened, and I climbed in. This was it! There was no way I was going to back down now, no matter how scared I was, I was going to go for it all the way. The doors opened and there he was.

We walked to our room and he ordered us some wine to loosen things up a bit. We talked a little more but I really had only one thing on my mind. He went into the bathroom and I decided to lie down on the bed, on my stomach with my chin resting in my hands. “I see you’re comfortable enough to get on the bed,” he said, with a slight smile. He crawled in as well, but closer to the headboard and patted the bed in front of him, which was a way of telling me to come closer to him. For that second I was no longer scared, and instead of getting closer I patted the bed in front of me, as if to say “No, You come to me!” I think we ended up somewhere in the middle but when we did I knew right then that this was 100% going to happen. He kissed me, and at the same time positioned himself on top of me between my legs. I could feel his hard cock in his pants rubbing up against my own pants-clad pussy. Every part of me was throbbing, and I could just feel my pussy getting wetter and wetter. The more he rubbed himself against me, the more I ached to feel my very first man inside me. He pulled my shirt up over my head as well as my bra and began licking and biting my nipples. It felt so good as I ran my fingers through his hair, my hard nipples in his mouth. He took his own shirt and pants off while I removed my pants and panties as well. His very hard cock was sticking out of his underwear and I just couldn’t help myself. I crawled between his legs and took him in my mouth. He felt so good in my mouth, hard and with pre-cum leaking out of the tip. I wanted to suck every last bit of it out of him. He tasted wonderful, and the more I tasted the more I wanted him.

He laid me down on the bed, on my back, and slowly spread my legs, but he didn’t enter me. Instead he took out two vibrators he had bought for me and slowly began sliding one inside of me. I’d never had anything in my pussy before except my own finger when I masturbated to this very fantasy I was living out. He was very gentle, working it slowly in and out of my wet pussy. After a little of that I felt I was ready. He oiled up his hard cock, laid down between my legs, and while kissing me slowly slid his hard cock inside me. I’ll never forget that feeling. His hard cock sliding into my tight pussy, filling me up. It was unlike anything I had ever experienced. It was a little uncomfortable, yet it felt so good at the same time. I didn’t know what to do. Did I pull him into me even deeper so I could keep feeling that wonderful filled feeling, or did I push him off of me so the pain would stop? I ended up doing both. As he began thrusting in I would put my hands on his chest to keep him from going in, yet when he tried to pull out I would grab his ass in an attempt to pull him in. Suddenly things really heated up, as his thrusting was getting harder. I wanted more, but to give my poor little pussy a break he pulled out and went down on me. And boy, did he know what he was doing. My hips were trusting up and down, and my breathing was heavy and fast. He licked my pussy getting me even wetter, till juices were practically flowing out of me then I grab him up to me and he entered me again.

We fucked like this for HOURS, him on top, me on top, kneeling in front of a mirror, me sitting on his lap. I remember how hot I got when I laid down on my stomach and he began rubbing his hard cock up and down my ass, finally putting it inside me as I felt his warm breath on the back of my neck and I clutched the sheets in front of me. Finally he rolled me over and placed my legs on his shoulders and began fucking me…hard, and fast. My aching and sore pussy was really getting pounded and I didn’t know what to do. It wasn’t just uncomfortable, it hurt, but it felt sooo good at the same time. The pleasure/pain combination was absolutely incredible. For something to feel so fucking good, yet hurt so much was quite a new experience for me. With my head thrown back and by arms up against the headboard I began to really moan. Every time his cock entered me deeply I would gasp “no”…I’m not sure if it came out as “no” but I was gasping/moaning the word for quite some time, but never really wanted him to stop. He suddenly looked at me and asked me when I wanted him to cum, inside me, or should he pull out. The thought of this man, whom up until today I didn’t even know, cumming inside me was quite an erotic thought but I couldn’t bring myself to let him do it on our first meeting, so I told him I wanted to see him cum for me. As he pulled his shiny cock out of my sore pussy he shot cum clear over my head. I had never seen anything like it. Instead of landing on my tummy (which we both thought was going to happen) he ended up hitting the wall behind my head, a small stream of which landed on my cheek. We were both in shock, and started laughing at what had just occurred.

At 20 years old I had lost my virginity to a 46-year-old man who knew exactly how to please me. I smiled and told him he had taken my virginity, to which he replied with a smile and a shake of his head “No, you gave it to me.” I fell asleep lying beside him, his arm wrapped around me, pleased that I had gone though with this meeting. It was one of the most incredible nights of my life.

The next day:

Apparently I had too much fun, for too long anyway, because I had to be rushed to the hospital where I sat in the ER for 6 hours. Turns out my night of hard fucking left me with what the doctor called “honeymoon cystitis” and (I quote) “severe vaginal trauma” – not uncommon, the Ob/Gyn told me, in women who engage in strenuous sex for very long periods of time, even when experienced…I just got a double hit because not only was that exactly what I had done, but I did it while losing my virginity. Greg, at 46, had laid me up for almost 2 weeks, while I had to take 2 separate antibiotics and pain medication…how many 20-year-old guys can say they did that to a girl just by fucking her? That was 2 years ago….and I still meet him for incredible sex. We have so many stories of things we’ve done, or want to do. He lets me ask for anything I want, and he in turn does the same. Nothing is off limits and nothing is out of bounds. We just ask…and get what we want…and even now he is still the only man to ever feel the inside of my pussy. He’ll have had me everyway possible long before any other man gets to even touch me!

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