(F/M) Breaking in a Virgin | 2016

I was talking with someone last night on the subject of virgins. This reminded me of one of my favorite times experiencing a virgin.

His name was Rob, nice looking, clean cut and about 6 ft tall. He wore glasses that just didn't look good on him but other then that I thought he wasn't a bad looking guy.

We were in the same class on got teamed up together on a project. Up to this pint I had never even talked to Rob and now I knew why. He was so nervous, his voice would crack every time he would start to speak to me.

It was a 3 week project and as the time wore on he did get more comfortable, not a lot more but just a bit.

On the final day, we wrapped up the project and I was pretty proud of us. We did a damn fine job on it.

"So where are you taking me to celebrate?" I blurted out, totally catching him off guard.

He just stared at me in shock. I smiled and said "seriously, take me out to celebrate!"

His poor face was red and his voice cracked "Um okay, I can pick you up at 8 I guess."

So the date was made, I headed home and got myself ready. I didn't have any real expectations going in, I was honestly proud of the work we did and just wanted to reward ourselves.

Rob showed right on time and we headed to a super nice Italian place that I totally loved.

Dinner was fantastic and after a bit of prodding by me, I finally loosened him up a bit. We talked about our childhoods, our likes and dislikes and all the other small talk people usually have.

I was really enjoying myself, Rob was super nice and respectful. He made me laugh and made me feel completely at ease the entire night.

We finished our meal and headed out. Rob drove me back to my house, we chatted some more and I have to say that I was kinda bummed when we pulled in the driveway.

I told him thank you so much and opened my door. I looked over and noticed he wasn't moving.

"Aren't you at least going to walk me to my door?"

He jumped out of the car quickly, met me at the front of the car and walked me to my door.

We stood in front of the door, I leaned in and gave him a kiss goodnight. Rob froze and hardly moved. I pulled back and asked "Are you okay?"

His face was red and he put his head down.

"I've never kissed a girl before." Rob explained, looking all sad.

It was like a shot of adrenaline being shot right in my brain. I knew I had to take Robs virginity and that's what I planned to do. I had to think fast on how I was going to get him to my room.

"Do you want to come see my favorite teddy bear?" I realized how dumb it sounded as I asked.

He nervously agreed and followed me through the house and in my room. I playfully jumped on my bed, grabbed my teddy bear and tossed it to him.

"Isn't he great?" I asked, not knowing exactly what my next move was.

"Umm sure, yeah he's cool" Rob replied.

I was hoping he would jump in my bed with me but I could tell that wasn't going to happen. I decided I would have to be forward and go for it all if I wanted this to happen.

"So do you think I'm pretty?" I sheepishly asked.

Rob stood there frozen for a few seconds before responding. "Yes I do" was all he said.

I figured I had him but was a bit afraid that I would scared him off but at this point I didn't care.

"Come cuddle with me then" I said to him.

He joined me on the bed and I wrapped my arms around him as I faced him. I looked right in his eyes and could feel that spark. I leaned in and kissed him softly, his hand rubbing back and forth on my back.

I leaned in to him and used my weight to lay him on his back. I kissed his neck and let my hand explored down his body. I could feel him tense up as my hand brushed by his cock but he didn't stop me. This gave me the green light to go further.

I reached my hands under his shirt and lifted it off of him. I kissed my way down his body as my hand clumsily undid his pants. I finally undid the button, slid down his zipper and slid my hand down.

His cock was rock hard and a bit bigger then I expected. I kept moving my lips down his body as my hands started to slide his jeans off. I sat up a bit and helped him remove them the rest of the way, his poor cock looked like it was about to burst. It was quite thick, his head was so red it was almost purple and precum was already leaking out.

I laid down and positioned myself between his legs, looking right at his cock. I wrapped my fingers around it and gave it a couple long slow jerks before stuffing as much into my mouth as I could. Rob let's out a long deep moan as my tongue swirled around his head. I worked his cock only a few times in and out of my mouth when Rob really tensed up.

I looked up at him and removed his cock from my mouth.

"Are you going to cum?" I asked as I stroked his cock slowly with my hand.

He looked up at the ceiling obviously trying to hold back. I started licking the underside of his shaft, just below the head and that was it. He grunted, his cock started jerking as cum started shooting out all over.

It had to be one of the biggest orgasms I've ever seen. Cum was flying all over, in my hair, on him, on my bed... It just kept streaming out. He was holding in his moan but his body was lifting off the bed as each convulsion ripped through his dick.

I let him recover for a minute then cleaned his cock off with my mouth, tasting his sweet sticky juice and to my surprise he didn't lose any of that hardness.

I climbed up on top of him, reached in my nightstand and pulled out a condom. (This was one of the few times in my life that I wasn't on the pill)

I straddled him and unrolled the condom onto his rod, it was a tight fit as his thickness really stretched the thin latex.

I stroked him a bit and asked if he was ready? He nodded that he was so I positioned the tip of his covered cock just inside my already dripping cunt. I moved my hips a bit and slid him in slowly, trying to let him feel every bit of my tight pussy.

I buried his cock inside of me and just sat there for a moment, looking at him and trying to figure out if the sensation was to much for him.

"Are you okay still?" I asked again. Another nod from him so I started sliding my pussy up and down his pole slow and steady. After about 6 full pumps he grabbed my ass and tensed up. He was struggling bad and his body was starting to shake, sweat beading up on his forehead.

"Did you cum?" I asked as he calmed down.

"No I don't think so" he replied.

I wasn't sure how he didn't know so I pulled his dick out of me and looked at the reservoir on the condom to see if it was full. I didn't see anything so I slid him back inside of me.

I sat up straight and buried him inside me, bouncing up and down on his dick but making sure not to do long strokes. I grabbed his hand and put it on my clit. His fingers pawed at my pussy like crazy, each time he hit my clit I made sure to let out a loud moan, trying to teach him where I liked to be touched.

He's a smart guy and figured it out and his finger rubbed my clit furiously. I kept bouncing as my hand made it's way to my nipples. I pinched and pulled them as I felt my orgasm starting to build as his finger and cock worked my entire pussy.

Just as I was about to that point of no return he tensed up and grabbed my ass hard. I felt his cock start jerking inside of me as he filled the condom with another full load of cum.

I was so happy I made him feel good but fucking frustrated as I was so close. I. Kept riding him but felt his cock getting softer, I knew it was over and I let his cock escaped my hungry slit.

I laid down with him and held him as he came back down to earth. We laid there and talked for a bit when I told him to go ahead and get dressed as I had to get up in the morning. (Total lie)

He kissed me goodnight and off he went. I on the other hand laid in my bed and got myself off 3 times just thinking about stealing his virginity.

Hope you all enjoyed.

-kisses