Twenty Dirty Dates Group Pt. 03

My friend Hanna and I were discussing the joys of anal sex over drinks one night after work. We both decided that turnabout was fair play, so we made a trip to an adult book store that sells sex toys and each of us bought a strap-on rubber cock. I was imagining that when a man started poking a finger in my ass I would ask, "are you hinting that you would like to have anal sex? That sounds lovely." Then I would pull my strap-on from my toy drawer and ask, "Which one of us gets to go first?"

It didn't work out quite that way with Kyle. I was giving him a blow job and teasing his ass with my finger when without thinking I just asked, "would it be alright if I got out my strap-on and fucked you in the ass?"

"As long as you have plenty of lube," he replied. His ass was no longer virgin when I finished with him that night, and the lube bottle was almost empty, I used a lot. I didn't feel like I dominated or humiliated him, I feel like he trusted me and was willing to indulge my fantasies. That's my idea of a badass man, he can take it as well as giving it.

Date Fifteen, First time—Kyle

We were at Ginny's house watching TV. She clicked through the channels twice, neither of us saw anything we were interested in watching. "We could always fuck," she said as she pressed the off button on the remote. Then she said nothing for much longer than you might have imagined.

"Or you could tell me about the first time you had sex with a woman," she said.

"Not blow jobs or pussy eating, I want to hear about the first time you had full penetration cock in pussy sex. Your first time was in a pussy wasn't it, not anal?"

"Yes, it was vaginal penetration," I responded. "But it was a mercy fuck, and I was a virgin for years after I got out of high school. I didn't have real sex until I was 21 years old."

"That's it, tell me more." Ginny said.

"I worked in a supermarket, mostly on the overnight shift, went to classes during the day. After a year or so I was kind of a jack of all trades at the supermarket. I helped the butchers, I loaded up the deli cases, I did maintenance work, whatever was needed. There was a girl named Diana who was a few years older than me, she worked overnight as assistant manager and there was never a manager on duty so she was really in charge. She also attended community college and we even had a class together."

"We never had sex at work, we were too busy for that, but sometimes between classes we would get together and talk. She would tell me about her dates and what they did. I would tell her about dates I had been on as well. Eventually she started telling me about the sex she and her boyfriend had been having so I started telling her that I had been having sex with my girlfriend, which was a lie, I never even got a hand job from the girl I was dating at the time.

One night at work we were both taking a break at the same time and she was all excited to tell me that she had had the best fuck of her life just before coming to work. I listened to her story and got all turned on and then it was time to go back to work. Half an hour later she paged me to come to the office. She said 'I just wanted to see if you still had that hard on from our conversation at break.' I did, but there was no time to do anything about it then.

"Between classes a few days later I started the conversation by apologizing to her for having lied and I told her that I was just making up all those stories I had been telling her about having sex. I told her that I was a total ass for making up all those lies and I would understand if she never talked to me again. I lied because I didn't want her to think that I was inexperienced. I looked at her and realized that she had tears in her eyes. 'Most of what I told you about sex I've been having was made up too,' she said."

"Then she asked me if I was a virgin, and I admitted that I was. She said that she was not a virgin but she had not had sex nearly as often as she had claimed. Then she really shocked me when she said, 'would you like to stop being a virgin?'

Two days later we both got off work at 6:30 am as usual. We both went home as usual, but after her parents both left for work around 8:00 am she let me know it was all clear and I went to her house."

"She had scented candles burning in her bedroom, soft music was playing, she was wearing a sexy nightie, and she smelled like mint and exotic fragrances. She put her arms around my neck and kissed me, the kisses became more and more passionate, both of us afraid to go any further. She had a way of sucking my lower lip between her lips, she was my kissing instructor."

"I'll have to thank her for that," Ginny interrupted, "she taught you well."

"We were lying together in her bed, I still had all my clothes on and she finally gave up on me making the move. She took my hand and slid it under her panties, then gave me instructions for stroking her wet pussy. I got my courage up and figured out how to proceed from there."

After a silence Ginny blurted out, "that's it? That is all you are going to tell me. I want to hear about the first time you pushed your dick into a pussy, I want to hear how long you lasted and where did you shoot your cum. You've got to tell me what it felt like. Don't leave me hanging like this."

"I got the panties and nighty off her, I did some breast handling, kissing nipples and that kind of stuff. Then I rolled over between her legs, she reached down and guided my cock into her pussy. Her pussy was so wet it was dripping and I slid right in all the way. She told me that she was on the pill and that I should cum in her pussy. I started pumping in and out and it felt incredible, but it only lasted about a minute and I shot my cum inside her."

I explained to Ginny that the second and third time I lasted longer and she said,

"So you went back to fuck her again?" Ginny asked.

"Yes, we had a lot more morning dalliances until I went off to university in the fall," I explained, "but I was talking about the second and third time we did it that morning."

Ginny held up her hand and we shared high fives. "You may have been a late bloomer, but you have learned well," Ginny said. "If you ever see her again, thank her for me, I grateful that she taught you so well.