How I Lost My Virginity (M/F) | 2016

I reached my breaking point, after many years, girls, crappy relationships and close calls. I thought I had the worst luck out of anyone I knew, so I finally caved and dipped my toes into the internet and its dating apps to go and lose my V-card.

About me, I am 26, fairly skinny, close to fit. I'm six feet tall, so I'm kinda like a beanstalk. Below the belt, I sport a modest six inches, but a very girthy six inches at that. Close to six inches in girth as well, which I've been told is somewhat ridiculous.

Several weeks pass, bleeding into months, and I wake up one Saturday morning to a message from an older woman, who seemed surprised that I found myself in the situation that I was in. She was very pleasant, direct in her communications, and wanted to meet up with me that same day.

After a brief chat, we figured out that it'd be best for us to meet at a motel, in between where both of us lived, to spare each other a long drive. After hanging up the phone, I quickly jumped into the shower to get cleaned up and trim the nether-regions to look appealing.

I arrived at the motel first, by a wide margin. I quickly shot a text message to the woman and after confirming that she was on her way, I went ahead and booked a room. As I walked up the stairs and toward the room, I could feel how anxious I was. It took all my nerve to not let the situation get the best of me. My hands were shaking as I placed the key card into the slot and entered the room.

Setting my things aside, I gave the room an overview. Very basic. Bed, bathroom, TV, Chair....then again what else would I need at that point. I tried to busy myself, but I was restless. It likely hadn't been 10 minutes, but I could've paced a hole in the floor. I sat myself down on the bed to calm myself down, when a knock came at the door. I walked over to the door, took a deep breath and swung it open.

On the other side, I saw this short, curvy, Latina woman (later I found out to be 36), with long, curly, black hair. She was wearing blue jeans and a grey sweater. We politely greeted each other with a hug and I invited her in. She immediately made a beeline for the king bed and stretched out, as she began to ask me questions about myself, and how I'd arrived to be in that situation. Conversation flowed pretty freely, and I felt myself relaxing a little bit, which was great. However, my earlier anxiety got the best of me, and I had to excuse myself to the bathroom to relieve the built up liquid.

After taking, what felt like the longest leak of my life, I'd cleaned up and was ready to head back out of the bathroom, but as I opened the door, there she was, but now only in a matching set of lingerie...a blue bra and thong. I froze for a moment.

She likely saw my pause and quickly dispelled it with a laugh..."This is what we're here for, right?" she asked.

I nodded like a goofball, but for once my brain decided to work properly and I made a move. I stepped around behind her, leaned down, and wrapped my arms around her waist. My lips found her neck as she threw her head back against my chest. We fell back against the wall across from the bathroom, as her plump, round butt mashed against my groin to find my rapidly hardening cock.

She moaned softly as I brought my hands up and softly squeezed her ample breasts through the bra. "Take it off", she whispered as her hands moved up my jean-clad legs. Moving quickly, I dispatched her bra to the floor, where I saw the rest of her clothes and I quickly noted that one of her nipples was pierced, and it was calling for me.

I turned us around and pushed her towards the wall with my body as I cupped her breasts with my hands. She shivered as they were a bit cold from my nerves, but that was quickly replaced by a moan as my lips closed around her nipple and my tongue circled the nub in my mouth, as I felt it stiffen. My other hand dropped down between her legs, as I rubbed her slit through her thong.

"Wait", she spoke breathily. I stood up straight and took a step back. Slightly bending down, she quickly shimmied out of her thong and kicked it aside. "Much better..." she said "...but now you're overdressed".

I quickly discarded my shirt, after which I found her hand unbuckling the belt on my jeans. She quickly unbuttoned them and lowered the zipper. In one fell swoop she pulled off both my jeans and my trunks, which cause my cock to pop into view for the first time. She tentatively made a grab for it and gently began to stroke my shaft. I gasped out loud from the sensation.

"My my, you're a thick boy". she spoke. "Is that a good thing?", I sheepishly asked "Oh, absolutely", she replied.

She let go of my shaft and walked over to the bed. She crawled up on all fours and shot a look back at me, before speaking a phrase that will live with me forever...

"What are you waiting for? Come here and fuck me."

Thankfully, I was still able to process something at that moment, but I reached down to the floor and fished a condom out of my pants, before walking over to her. I tore it open and rolled it down over my head, and with a little struggle, down the rest of my shaft.

As I stood on the floor, she backed up and arched her ass into the air, by the edge of the bed. I walked over and placed myself between her legs, my cock rubbing up against her glistening slit. She moaned again as I softly ran my hands up and down her back once, before I grabbed my cock and gently led it to her opening.

As the head slowly entered her pussy, she gave out a loud "Oh. Okay...Go slow". I obliged of course, slowly pushing the rest of my cock into her until my hips rested flush against her ass. "Oh my god..." she moaned out loud again. "..you are THICK...start slow...please".

I was determined. I was going to do as I was asked, and I really didn't want to bust too quickly...but the feelings were overwhelming. My cock was enveloped in this warm, wet paradise and felt like it was being massaged from every angle...even through the rubber. I slowly began to pull myself out and pump back in. I stared straight at the wall in front of my and took deep breaths, trying to control myself, despite the noises coming from her. The moans increased in volume and frequency. It must've been no more than two minutes before she grabbed my thigh and begged..."Go faster...and don't stop, no matter what".

I grabbed hold of her hips and slammed her all the way down on my cock, as I began to move back and forth at a quicker pace. She quickly grabbed a pillow and muffled herself and she was moaning louder and louder. Her body was covered in a sheen of sweat now, as our bodies collided over and over. Her legs began to shake, and I quickly felt myself reaching the point of no return.

"I'm going to cum", I warned her, to which she replied with a loud moan and a "Do it. JUST DON'T STOP".

I started to pound away and give her everything I had, for as long as I could. I slammed into her, feeling her wet pussy sliding up and down my shaft. Gripping me as I slid out and accepting me as I slid back in. That was all too much for me...in a few short moments, I felt my cock pulse as I began to shoot my cum into the rubber. It felt absolutely amazing, I couldn't tell you how long my orgasm lasted, but I'm pretty sure I temporarily forgot where I was, and nothing else mattered. As I felt that I was spent, I bent down and kissed her on the neck and her back, only to find that her entire body was softly shaking.

"Hey, are you alright?" I asked, "Everything OK?"

She replied, gasping for breath, "Yeah..you just...you made me cum really hard"

I kissed her on the back again as my now soft cock fell out of her pink, slightly swollen, pussy. As I took the condom off, she rolled over to her side and exclaimed, "WOW that's a lot of cum. You must have been really excited"..to which I just sheepishly grinned back.

As I walked into the bathroom, I was over the moon. Not only did I lose my virginity, but I made her cum too...and it seemed like she really enjoyed herself. I quickly disposed of the condom and went back to bed, to find her covered up. I slid in next to her and wrapped my arm around her waist, pulling her close to me. I kissed her on the neck and whispered, "...that was amazing".

"WAS?" she replied loudly. "Oh, I'm not done with you just yet" she said, as she reached behind her and wrapped her hand around my cock once more...

"Think you've got another go in you, big boy?"

Did I ever.

Hope you guys enjoyed this. This was my first go at erotic writing, but this memory was pretty fresh in my mind, and I didn't want to lose all the detail...so I decided to share it with all of you.