Getting the Experience [m/f] | 2016

Nicole and I met in the middle of our freshman year of college. We were both from the same home town and ended up sharing a ride home with a mutual friend. We had a few classes together, which led to us studying together, which led to us hanging out quite a bit on nights and weekends.

Nicole was very outgoing and honest. She didn't drink, and she readily admitted that she was a virgin. One thing she didn't realize was that she was really cute, but it was obvious to me with all the attention she got when we went out to parties together. On more than one occasion, she used me as the "fake boyfriend" to get rid of a guy who was too clingy. Every time I walked her back to her apartment, I thought about how amazing it would be if it didn't end at the door, but I knew she was waiting for the right guy, and I also knew that guy wasn't me.

It was the beginning of our sophomore year when Nicole met Ryan in one of her classes. He was polite and handsome, and like her, he didn't drink. I found out over time that Ryan had had a religious upbringing, and he seemed pretty perfect for Nicole. Through one of her friends, I found out that he was also a virgin who wanted to wait for the right girl for his first time, which was welcome news, because I knew Nicole deserved a nice guy like that.

In time, Nicole shared with her roommate and me that she and Ryan had been having sex. She said that the first time wasn't great, but she figured since neither of them had done it before, it could only get better with practice. We assured her that it does, and that the first time can be awkward (probably more so for women than it is for men, I admitted). This didn't seem to be helping her, and she eventually admitted that they had had sex four times in total, and each time, Ryan seemed more nervous and uncomfortable with her. On top of that, he had only had an orgasm the second time, and she hadn't even come close.

Nicole broke up with Ryan a few days later. We got together in our hometown the day after Thanksgiving, and she told me that he was a sweet guy, but he obviously wasn't ready for a physical relationship. As the night wound down, we continued chatting, and Nicole revealed a few things about their short relationship. First of all, having sex had mostly been her idea. Second, she had wanted to try oral sex, but he wouldn't let her. Third, even though the first time was awkward, it still felt good, and she wanted the full experience. She assumed that with practice, Ryan would improve his form, and give her what she was looking for, but he wasn't around long enough for them to find out.

"I'm not a prude," she told me. "I just don't want to sleep with guys I don't trust." That was a game-changer for me. I had always been a bit cautious in these conversations, not wanting to offend her, but after hearing this, I was prepared to be a little more open with Nicole.

I pressed a little harder during our next conversation, which occurred via text, two days later, while her parents drove her back to campus when Thanksgiving break was over. It was at this time that she admitted that she knew "how to get herself off," but she knew it would be better if it were someone else doing it to her. I shared some of my more explicit thoughts on my experiences, and gave her some pointers on what can make a good or bad experience.

This conversation led to another large admission on Nicole's part. That Saturday night, one of her high school friends had talked her into trying some wine, and she ended up getting drunk for the first time.

"I loved it! I'll definitely have some drinks with you guys next time we go out," she promised, adding that we'd have to keep an eye on her and not let her get too drunk.

That Friday, we went out to a house party, and Nicole sipped on a few mixed drinks throughout the night. I wasn't counting, but she couldn't have had too many, because she was still the most responsible acting member of our group when we left that night. I walked her home again, but this time she invited me inside. "I brought back a bottle of that wine I tried last week. Want to try some?" She poured us each a glass, and we chatted on her couch. The wine must have pushed me over the edge from buzzed to drunk, because before I knew it, Nicole was leaning in to kiss me. I didn't resist, even though I knew it probably wasn't a great idea. We kissed for a few seconds, and she sat back and smiled. "Sorry," she said, "I hadn't had a kiss in a while and I was feeling bold." I assured her that it was okay, and we went back to our wine.

With both glasses empty, Nicole let out a big yawn. She offered to let me stay the night, which I accepted, expecting to sleep on the couch. To my surprise, she invited me to her bed. We kissed a bit more, and my hands ventured down to feel her ass, but that's as far as it went. We fell asleep in each other's arms.

When we woke up, we laughed about the previous night, and Nicole teased me for feeling up her butt. I was relieved that she was okay with what had happened, but throughout the day, I realized that she had instigated most of it, which I didn't think much about until she texted me later that night.

"Want to finish that wine?" She asked.

"Does it get me another kiss?" I joked.

"Sure. And another butt squeeze if you play your cards right ;)" She teased. I wasn't sure if either of us were joking, but kiss or no kiss, I wasn't going to turn her down, especially if there was even a remote possibility that I could get another handful of her round ass.

We were almost finished with our first glass when Nicole's roommate headed out for the night. When the door closed behind her, Nicole put her glass down and kissed me. "You know why you're here, right?" she asked.

"I had a pretty good idea." I said, nervously looking at my feet. She lifted my chin to kiss me again, and I fell forward on top of her. We kissed for what seemed like forever, but I never got bored with it. She was a very passionate kisser, and she let out a small moan every few seconds, which I found adorable.

Eventually, Nicole led me to her bed. "How about that butt squeeze I promised you?" She asked, sliding her jeans down to reveal a pair of red lace panties. I followed her to the bed and laid down next to her, grabbing a handful of her ass as we kissed some more. In time, my confidence was growing, and I moved my hand to the front of her panties. She responded by reaching down and pulling them off. I kissed her one last time and moved down the bed so I was laying between her legs.

She was completely smooth and hairless. I leaned in and kissed above her clit, sending a shiver up her spine. My mouth moved down a bit, and I started to massage her clit with my tongue. She gasped in excitement. "No one has ever done that before." I slowly worked a finger inside of her, which she seemed to enjoy, and before long, I was able to slip in a second. Our eyes met as I licked her, and I could see how much she enjoyed it.

She motioned for me to come back up to kiss her again. Our lips locked, and her tongue explored my mouth. Ready to take things further, I asked "Should I get a condom?"

"You don't have to," she shook her head. "I'm on the pill." I stood up next to her bed and stripped for her, taking extra time to slowly reveal my already hard cock. She wrapped her hand around it and awkwardly stroked it a few times. "I've never felt one with my hand before," she admitted.

I gently pulled her hand away, and positioned myself in front of her on the bed. I slid the head of my cock over her lips, using her wetness to lubricate it. After a few strokes against her clit, I slowly pushed inside of her. She was very tight at first, but after a while, she opened up around my cock. I leaned back down to kiss her while I slowly pushed in and out of her.

"Does it feel good?" I asked.

"Yes." She moaned softly, waiting for my lips to return to hers. Her pussy felt amazing, and after a while, I knew I was going to cum way to fast. I got a few last strokes in and pulled out before I was able to start cumming. I slid myself down and returned my mouth to her clit. This time, I worked my fingers a little harder. After several minutes, she managed to say "Don't stop." I pushed my tongue harder against her clit with each stroke and continued working my fingers in and out of her. A minute later, her legs tensed up and she started to moan and shake. I did my best to stay in position, but eventually she pushed me away when her clit couldn't take anymore.

I laid in the bed next to her as she recovered and I asked "Was that better than by yourself?"

"Yes," she let out between breaths. "Way better." I gave her another minute to rest before I rolled her over on her stomach and gave her ass a nice squeeze. I sat up and instructed her to get up on her hands and knees. I got behind her and slowly pushed inside of her pussy, grabbing her hips for leverage.

I leaned in to kiss the back of her neck, and asked "Where do you want my cum?"

"Just not inside me," she answered. I went back to an upright position and focused on Nicole's beautiful ass in front of me. Before long, I was pulling out and spraying my cum all over her ass and back. She collapsed onto the bed, breathing heavily and smiling. I ran to the bathroom to grab her some tissues to clean up before laying down next to her again. We kissed again and wrapped our arms around each other.

"That was hot," Nicole told me.

"I thought so too," I agreed.

She told me what she liked about it and what else she wanted to try. We had sex two more times that night. She tried being on top of me, and I walked her through giving her first blowjob. Overall it was an amazing night. We agreed that we could have sex again, but we shouldn't do it too often, so that we could still try to stay friends if either of us started dating.

A few months later, we had a repeat encounter during which she asked me to cum in her mouth so she could see how it tastes. We discussed trying anal sex, but after she attempted to experiment with a toy and didn't enjoy it, she decided not to. We had sex every few months until senior year when she met her husband. When she got engaged, it was hard for me to accept that we wouldn't get to be together again, but overall I was happy for her.