My sexual autobiography did not begin at the beginning, but this story answers the question, “where did you lose your virginity?” which I saw on the forums. I hope you enjoy it.

What were you doing on Friday, September the first 2000? Cast your mind back. Was it a normal day at the office? Perhaps you were a blushing bride, excited about her wedding the next day? Were you looking after young children who are now all grown up? Maybe you had just retired and were settling into your armchair, enjoying your new freedom.

If you were not yet born, please don’t make me feel old by mentioning this in the comments.

If you are of a similar age to me, you might have been excitedly looking forward to setting off for university very soon, as I was. Perhaps, like me, you might also have lost your virginity that day.

Now, I did do a story once loosely based on how it all happened. It’s called “Rebeca takes the plunge”, and you might enjoy it. That story was heavily fictionalized. Essentially, a young woman has a friend that she is very attracted to but who embarks on a path of self-destruction. I’m sorry to say that this aspect of the story was wholly truthful. 

Felipe was kind and smart and polite and he made me laugh out loud more than anyone. When our friendship group…we were not dating so we didn’t go alone together…went to the beach, he was so hot, bare-chested and wearing only swim shorts. All the boys were shirtless, but I had eyes only for Felipe. 

One by one, we were all turning eighteen, and we began to drink alcohol when we hung out. I’m a moderate drinker, but Felipe quickly developed a taste for it. One day, we went out in a big group. There were about twenty of us, sitting at tables outside in the warm summer air. We were both tipsy. I got up to go to the bathroom. Felipe seized the moment. He took my hand and led me into the restaurant and, out of sight of our friends, (not that anyone wouldn’t have known) he kissed me. I kissed him back. It wasn’t my first kiss, but you could count the number of boys I’d kissed on one hand. It clearly wasn’t his first either, for he kissed me well.  

I wanted him to be my boyfriend. I wanted him to be my first. Based on the lump I felt pressing into my crotch through his trousers, I’m pretty sure he wanted to be the first too. But we were still living with our parents and there was no way we could bring someone home. 

In the cold light of the next, sober, day the moment passed.

When you are just eighteen and you’ve been raised in a happy, rather sheltered middle-class home, seeing someone you care about sink into alcoholism is a truly shocking experience. I saw him drink a lot, but what I saw was the least of it. Stories began to mushroom about Felipe falling asleep at house parties, being seen drinking every night, being taken home in a police car having been found passed out…

I tried to reach him. But I failed. I was young and naïve. I didn’t yet know that an addict only recovers because they want to and because they have, at least partially, dealt with the demons driving their self-destructive behavior. Simply sitting down and saying, “I’m a bit worried about you…” doesn’t get you very far.

Felipe is stepping, or perhaps staggering, off the stage for now.

                                                                                                *

I met Enric at the birthday party of a classmate, at the bowling alley. Felipe wasn’t there. Enric was the birthday boy’s older brother. He latched onto me straight away. It did not take long for his charms to have an effect. When I told him about university and what I was going to study, he didn’t feign interest in a lame way; he engaged me in intelligent conversation on the topic. Intelligent conversation is the key to my bedroom.

He wore jeans and a Ralph Lauren polo shirt. He had black hair in a crew cut. We nonchalantly sidled away from the birthday party and found ourselves a table to share. He walked me home and kissed me at the door. I gave him my number.

And then, a miracle. If this hadn’t happened, I probably wouldn’t have this story to tell.

“MC1982,” my father said, a few days later, “You’ll have to take care of yourself for a weekend. Your mum and I are going to visit some friends of ours in France. Your sister will stay with your aunt. You can call us if you need anything.”

 My older brother had already left home, and my younger sister would stay elsewhere. I would have the flat to myself for a night for the first time.

I did not immediately sit down with a drawing board and meticulously plan to lose my virginity that weekend. But when Enric called me, I accepted his offer of a date, and I knew full well that the house was empty.

We met at midday. We walked about together. We ended up at the beach with sandwiches and chocolate and a bottle of Coke. I didn’t have a swimsuit or a bikini on, just shorts and a T-shirt. Enric took his shirt off. We kissed. Kissing a bare-chested guy was as far as I’d gone up to that point. My hormones were going wild now. We made out for ages, at least an hour.

“My parents are away. We could get a pizza at mine?”

I saw his eyes widen just a little.

“Sure.”

I imagine for many people that their first time is spontaneous. Well, I had a thirty-minute walk home to get used to the idea. Was I nervous? I was terrified. Would it hurt? Would he like my body? Would I accidentally get pregnant? I knew I’d have to try it sooner or later, and he was hot, but still…

Enric stopped outside a pharmacy.

“Wait here,” he said. I watched as he strolled nonchalantly in and bought a six-pack of condoms. His confidence was sexy. I had some at home, but his evident intention to use protection was reassuring. Suddenly, I could hardly wait! I looked him over at the till, thinking he’d be naked in half an hour…

We got home. I went to the bathroom, fixed up my hair, and brushed my teeth. He asked permission to use the bathroom, which I thought was sweet. When he emerged, I poured two glasses of water and handed him one.

“Let’s drink these…in here,” I said, and led him to my bedroom, which I was glad to see was fairly tidy and airy. I'd thought about where I would have my first time. Would it be at my lover's place? Or in a hotel? Or here, in the bedroom, I'd slept in my whole life? The bed had changed to adapt to me growing up, but the room was the same one I'd been given when I was brought home from the hospital. So I lost my virginity in the only bedroom I'd ever known.

We closed the door and sat on the edge of the bed. Suddenly, shyness and nerves took hold, and it grew awkward. Enric put his hand on my knee.

“First time?”

Blushing, I nodded. 

“Ok. It’s not mine. I had a girlfriend last year. MC1982?”

“Yeah?”

“You have to relax, ok? You can’t be all tense.”

“I know.”

“You want to do this?”

I read once that plants, when cut, actually scream, just at a decibel level we can’t hear. My vagina, at that moment, was doing something similar.

“Yes! Yes! We want to do it!”

I said nothing, but I reached for the hem of his t-shirt and pulled it up, exposing his belly. Now, of course, it’s almost impossible to get someone else’s shirt off without their cooperation, so I let him disrobe and pulled my own T-shirt off. We kissed then, passionately. Our hands fell on each other’s upper torsos. Nimbly, Eric reached around and unhooked my bra. I slipped it off my shoulders, baring my breasts. I felt him look me over, then he looked deep into my eyes and kissed me again. As our tongues melded, I felt his hand take my breast and cup it, holding it gently, and then he pinched my nipple. Mmmm…very sexy.

We scooted back and lay on the bed together, then continued to kiss, our legs intertwined, which was nice. After ten minutes of that, it was time for the big reveal.

“I think these need to come off,” he said, tugging at my shorts. Smiling, I rolled to my back and pulled them down. He quickly did the same with his shorts, we briefly kissed again and then we giggled about,

“On the count of three!” and stripped off our underwear, the last of our clothes.

I knew the human anatomy, of course, but a naked man, in person, still amazed. His penis didn’t contain any shocks. It was about how I’d expected it to look. But the whole man, completely naked, was a sight I found hot and attractive, but also kind of beautiful, in a way. I felt oddly moved by the sight. Feeling this surprised me. 

He kissed my chest and my tummy, then came back to within kissing range.

He reached for my genitals, and I reached for his. It took some whispered questions and answers, but he found my clitoris. I jerked him up and down. It was very hard. I thought about attempting to suck it, but something stopped me. My first blowjob took place on another occasion, previously told in this series.

Foreplay didn’t last very long…we both wanted to have sex. He put a condom on and approached me. I opened my legs, feeling a little self-conscious, but anxious to get on with it.

He teased me a little, which was hot. He tapped my belly button with his cock three times, then he dragged it along, down my stomach to my crotch. He pressed gently at me, entering partly but not wholly. I could feel my vagina cautiously welcome this intruder, step by step gaining enough confidence in this strange, hard cylinder to admit it. He pressed a little further, then pulled out. Was I turned on? I was practically shaking. He pressed in deeper then withdrew again.

“Please, get in there,” I remember whispering. I was very wet now.

The third time, he teased entry again. And then he pushed inside me. Wow! It felt different from having my fingers in there, and the fact that he was naked and close to me made a massive difference. His smell, and the feel of his hair as I ran my fingers through it. I liked the feel of his arms and his back. I enjoyed kissing him deeply.

He was very gentle. He thrust very slowly until my hymen broke. There was a brief pain, but not serious. He built up his stroke. I began to think, what should I do here? Should I just lie back and…take it? Can I make anything happen for him? I reached down and gave his balls a gentle squeeze. He smiled and kissed me.

I lay back, looking at the ceiling. I’d done it! I’d lost my virginity and it hadn’t been gross or disgusting at all. It felt good, in fact. Was I going to orgasm?

Alas, it was not to be. Enric suddenly sped up, then he lost control. His face contorted and I felt his cock shudder as he orgasmed.

“Sorry!” he said, sheepishly.

“It’s fine,” I said, and I gave him a smile to reassure him. Poor Enric was terribly embarrassed. He blushed and cursed himself, holding his hands over his face.

“It’s ok, really,” I said, kissing him.

And it was. I’d been warned not to expect fireworks the very first time. I was only eighteen. And he could try again. I knew guys were supposed to last longer when they’d just come. What mattered was that I’d crossed the threshold.

After about twenty minutes, his penis came to life again. I helped it along with my hands and we were good to go. His condom slid easily on.  

The second time I had sex was the first time I tried both doggy style and cowgirl. There were about ten minutes of missionary to start us off, then he suggested that I try riding him. I found lowering myself onto him from above hot as hell. Enric’s eyes were riveted on my body as I eased his cock into me. His eyes were boring into my breasts and belly, which he now rubbed. He was hot for me, dull, quiet old MC1982, who sometimes wondered who would ever fancy a bookworm like me. Well, apparently, I’d had nothing to worry about.

I rode his cock and it felt different, but really, really good. His penis was reaching further inside me, and I used my weight to move up and down it like a piston. Enric reached up and fondled my breasts, pinching my nipples, and I asked him to keep doing it. I was getting wetter and wetter now. I could feel my pleasure growing, feel my arousal grow, feel my sexuality finally let loose and enjoying its new freedom. I looked down at my naked torso. I saw my breasts bump gently up and down. I saw Enric’s bare chest. I could hardly believe this was happening. I was…having sex!

I already knew I wanted a third time with Enric. And a fourth. And a fifth. I rode his cock, and I thought about all the opportunities for sex that lay ahead of me…

I can’t be sure there was a connection, but thinking about having sex again, even in the middle of the act, flipped the switch for me, I came, a lovely burst of pleasure inside. It wasn’t my first orgasm…I’d achieved that through masturbation.  It wasn’t the hardest I ever came. But it was a first orgasm during sex. I rubbed his chest and kissed him appreciatively, secretly hoping it would be the first of many.      

Enric and I did it all night. I cannot, in fact, remember how many times we had sex that night, but it was a lot. I had gone to bed a girl and I got up the next day a woman.

I know I am lucky, in that I had a good first time with a decent man. I know this is not true for all women, and I appreciate it. And, to conclude the story, if you are a young woman who is still a virgin, I highly recommend losing your virginity to someone you know is a fling, as I did. Not a one-night stand. Not a long, committed relationship. A fling. Learn the basics with a fling, then put it to the test with your first serious partner. It works. Trust me.

                                                                                                *

I lost touch with both Enric and Felipe when we went to college, but Felipe and I happened to meet in the street one day. He told me he had cleaned up and quit drinking recently.

We were thirty by then. Ten years of heavy drinking had held him back. Felipe had underachieved in his professional life and was alone. Perhaps in another life, someone…I… could have saved him. Perhaps it was his fate.

In the story I mentioned earlier, “Rebeca Takes the Plunge”, the girl marries the guy with a self-destructive streak. This Disney-ish ending did not reflect my reality. Felipe is my sliding doors guy. I don’t ask the question wistfully. I am happily married. But in another life, perhaps he could have made the best of his life and I would be telling a story in which he had popped my cherry.