For my first post on this sex blog, what would be more fitting than the story of how I lost my virginity – at quite a late age I might add. I was 22 years old and though I had many opportunities to lose it prior, I never went through with it. After going through multiple personal and family situations after high school, sex wasn’t on my priority list. But you’re not here to read about that! So let’s get to the juicy/awkward details of my first time.
You may notice a key aspect in all of my posts will be online dating and this is no exception. I met “S” on OkCupid, in fact she messaged me first. She was the comic book nerd type and beautiful – I couldn’t believe she was messaging me. We really clicked and began talking on the phone nearly every day for three weeks. She lived about an hour South from me so finding time between our schedules was difficult. Finally we made plans to meet, she agreed to come visit me at my house.
I remember being nervous just anticipating her knock on my door. Once the doorbell rang my heart began to race. When I opened the door I was surprised to see she looked exactly like her profile picture. I welcomed “S” in and she brought me a card and a poster for one of my favorite shows. I felt embarrassed because I hadn’t gotten her anything. We hugged and then made our way into the living area. I sat down on the couch and she sat down right beside me; her perfume was intoxicating.
“S” and I sat talking, joking around for over an hour. Eventually she asked if she could take a photo to show her friends I was in fact who I said I was. We got close and she lifted up her phone and as soon as she hit the capture button she leaned in and kissed me on the cheeks for the photo. That was the cue I needed; I had been nervous all day about how to make a move and suddenly I was completely comfortable with her. I turned and kissed her on the lips and she pushed forward kissing me back.
We made out on the couch for over an hour. I was on top of her when she revealed she had her period. A sense of disappointment, yet relief washed over me. We continued to make out as I slid up her shirt and felt a woman’s breast for the first time; I rolled my thumb over her nipple trying to do everything I had read or seen over my horny teenage years. “S” moaned and unbuttoned my pants, sliding her hand down past my underwear and getting a tight grip on my hard cock. She began slowly stroking me as we continued to kiss and feel each other’s bodies – another first for me. Eventually we ended our date after the sun went down and we were both happy, making plans for the next weekend where it finally happened.
* * *
“S” decided to come back to my house the next weekend, we had discussed the possibility of sex prior and I bought condoms just in case (I bought them online because at the time I was still embarrassed to go into a store and buy them). She came over, we greeted each other with a kiss and went back to the living area; sitting down on the same couch we made out on last week. The two of us love Trivia and would play against each other throughout the week on our phones. I suggested we play Trivial Pursuit with a catch. Anytime one of us would win a pie, the other would have to take a piece of clothing off – that is right, strip Trivial Pursuit, try it at home.
The game ended up being lopsided and I became quite lucky, even guessing a few answers right. “S” had one pie and I had five, she sat in nothing but her neon green panties but covered herself with a blanket. I remember getting some questions wrong just so she wouldn’t feel weird being the only one naked. The game never concluded once I got down to my underwear, she stood up, took my hand and lead me into the bedroom.
We laid down on the bed and made out, feeling each other up and removing the remaining clothing we had on. “S” turned to me and asked if I had bought protection. Ironically I had placed the condoms inside an old baby carriage I was trying to sell… The catch was it was across the room and I hadn’t been naked in front of anyone before, but those nerves were outweighed by the promise of sex. I walked over and pulled one condom out of the box and crawled back into bed as she stared at my naked body the entire time.
I opened the package and was about to slide it on when she said “I can do it if you want.” It wasn’t like I didn’t know how to put on a condom but that was an offer I just couldn’t refuse. Handing her the condom, she rolled it down my shaft as chills went up my spine.
“It is your first time,” she said. “Let me take care of you for your first time, just lay back and enjoy.”
“S” climbed on top of me and immediately reached between her legs to straddle my cock. I felt her sink down on my cock; I remember thinking “That’s it, my virginity is officially gone no matter what happens from this point on.” She began riding me, he breasts bouncing in my face as she leaned forward. We kissed, her long her spilled down and kept getting in between our lips as the sound of her body smacking down on me echoed throughout the room. I was inside this girl, but still felt skeptical about touching her – an insane thought looking back.
I built up the courage and being an ass man, I went right for hers. Grabbing two handfuls of her ass cheeks I squeezed and massaged them. After a while she grabbed my hands and slid them down lower to her thighs. “S” was beginning to moan and I felt nowhere close, I was surprised that my first time I hadn’t ejaculated as soon as I entered her (the start of an issue I never knew I had).
I didn’t want to lay there so I flipped her onto her back (alright I asked her if she could get on her back). I positioned myself between her legs; she looked up at me with a smile when I had my first embarrassing moment. I hadn’t realized how low her entrance was and did my best trying to find my way back inside of her. “S” began to laugh and I in turn laughed at my botched attempt. She reached down and slid me inside her myself. At the time I didn’t want to put too much weight on her so I remained on top of her with my palms planted in the bedding and arms fully extended. My arms got tired quickly but I fought through it as we both were breathing heavily, mine not for pleasurable reasons but the fact I was becoming exhausted.
She became just as surprised as me that I hadn’t cum yet. We tried doggy style; again having trouble entering her, but I ended up being able to for the first time by myself. Finally we both collapsed to the bed and she pulled my condom off and wrapped her lips around my cock. It felt amazing, but still I didn’t feel like I was close to climax. I offered to go down on her, but she said she wasn’t a big fan of that. This was the beginning of finding out that only I could get myself off after a lot of work; a side effect of the pills I take. It is bittersweet because I don’t get to feel what it is like to cum mid sex, but on the plus side I can last really long being hard the entire time.
I ensured her it was fine that I didn’t finish and I wasn’t lying. I enjoyed the sex and the fact I didn’t cum did not spoil the moment. We put our clothes on and went out for dinner. I remember her jokingly saying “I feel like the devil now,” because she had taken my virginity.
That is it, the story of how I lost my virginity. In case you were wondering she was nineteen at the time and was not a virgin as I’m sure you can tell from the story. Looking back I know I put a lot of significance behind my first time, but I shouldn’t have. I didn’t suddenly become a man that day, in fact nothing changed at all. On the plus side it wasn’t as awkward as I anticipated and I was completely comfortable with “S”. We dated for another few months but things didn’t work out and she ended up being in a relationship with another woman during college. She’ll always hold a special place in my heart though.