The Claudia Story

"I've had anal sex with several guys." She answered.

"Did you like it?" Randy replied.

"I have enjoyed it when I have done it previously," Liv responded.

"What was your first time like?" Randy asked.

"I kind of already answered your question, but I don't mind telling the story. This was when I was nineteen on a family vacation. We all went, my mom, dad, and younger brother. We went to Greece for a week. As it was a family vacation, I didn't really get much chance to let loose. One night though, we went to this really nice restaurant that served fresh fish. The food was amazing, but that's not the important part of the story. The waiter that served us was this really handsome guy." Liv told them.

"How old was he?" Ffion asked.

"I never asked, but he was maybe twenty-five. He was this really hot, olive-skinned guy. We were subtly flirting the entire meal. I was trying not to make it too obvious to family. I agreed to meet him later that night. After we got back to our hotel, I snuck out and met him on a local beach. I was all over him the moment I saw him. He went down on me for ages before we fucked. He had me climax a few times, and I told him I wanted him to go where other guys hadn't gone before. I had some lotion with me which wasn't the best lube, but it worked well enough. He went slow as I'd never done it before." Liv continued.

"How big was he? Jana asked.

"I think about seven inches. He wasn't very thick. We did it in doggy, and he went really slowly, working a few inches into me gradually until he was completely inside me. He fucked me slowly. His cock felt incredible inside me. I think I went somewhere else in my head for a little bit, it was just this pure animal lust overtaking me as he fucked me like that. I came so hard on him. He eventually pulled out and came all over my back. I washed myself off in the sea before sneaking back into the hotel room. The next morning, I don't think either my dad or brother suspected anything, but I think I must have been glowing, as when I was alone with my mom, she asked me if he was really good. My boyfriend at the time was very happy to discover his girl wanted to try anal with him," Liv told them, finishing her story.

"What about the rest of you girls and first-time anal experiences?" Kieran asked.

"I'll allow this one as another group question," Jana told them.

"I've never done anal with a guy, but I've had girls use toys on me before. My first time was with an ex back in high school. She wanted us both to try it, so she bought some plugs and some dildos. She used the plug on me first, and I kind of felt weird and uncomfortable at first, but I started getting used to it. I loved having her tease my clit while she fucked my ass with the dildo." Beddy told them.

"Have you done anal Fi?" Liv asked.

"My first time was with an older guy." Ffion started to recount her story

"Now I understand". Beddy commented

"I was eighteen. Still living at home with my parents, and then for a couple of months one of my dad's friends was living with us. He was going through a messy divorce, and she had kicked him out and was likely going to take the house. I've never been certain about the details, but I think she had been having an affair and they split when he found out. He was this really handsome, well-built older guy in his early fifties. I was attracted to him the moment he was living with us and touched myself so many times at night thinking about fucking him. I teased him all the time, walking round the house in really tight tops and tiny little shorts. I was really proud of my bust and loved it when I knew I was getting attention from guys." Ffion explained.

"Such a tease. Did he notice?" Liv asked.

"Yeah, I caught him staring all the time. There were a couple of times when I saw he was hard too. He looked big as well. I finally got my chance one weekend when my parents were away, and it was just the two of us. We were in the kitchen one morning, and I was really turned on. I taunted him, saying if he was just going to stare or if he was going to do anything about it. Next thing I was bent over the kitchen counter with him inside me. I loved how big he was. I'd been with a few guys who had been thick, but he was both long and thick. He fucked me really hard, and I came on him a few times. He made me suck his cock and came in my mouth. This was the first time I'd let a guy cum in my mouth. He tasted good, and I loved swallowing him. I was really wet and aroused. I asked him if he wanted to fuck me in the ass."

"What was his response?" Dan questioned.

"He was surprised at first. He told me his wife wasn't into it and he hadn't done it with a girl since college. I had lube in my room as I'd started experimenting with anal play a few weeks earlier. I might have been subconsciously preparing myself for this moment. He lubed me up and just covered my ass and his cock in it. He fingered me for a while until I was loose enough for his cock. He pushed just the head in, and I knew I was dripping at this point. Just having the tip inside me felt incredible, I loved how tight I felt around him. He worked it in really slowly until he was fully inside me. What Liv said earlier about being overwhelmed, I could feel every inch pulsating inside me. I just wanted him to stay deep like that a little longer. He started to fuck me slowly at first and then a little harder. I wasn't even sure I could orgasm being fucked like that, but I came really hard on him, and I just felt his cock explode inside me. I was whimpering as he dumped his load into my ass. The two of us just stayed like that for a moment, not talking, and then he pulled out of me. It was weird after we just continued like nothing happened. " Ffion finished her story.

"Fi." Olivia remarked, pointing at her friend's crotch.

Ffion hadn't noticed when recounting her story how turned on she had gotten. Her panties now had a very visible wet patch. The redhead simply smiled in response.

"Your turn, Jana," Ffion told her.

The blonde sat up straight in her beanbag chair. "So this was at my previous college before I transferred. My English literature teacher was quite young he had only recently finished his own degree and moved into teaching. He was really cute, and I had a massive thing for him. I wanted him, and I was going to make him mine. I always sat in the front of class, wearing tiny little skirts, and would flash him panties, or on days when I was more daring, wouldn't wear any. Sometimes I caught him looking or pretending not to notice. This continued for a few months, and one day he pulled me aside after class and asked what I was doing. I was completely honest with him, I told him how much I was attracted to him, and I really wanted him to fuck me. He was telling me all about ethics, that it would be crossing boundaries as a teacher. I bent over his desk and exposed my ass to him. I can't remember if I was wearing panties or not. I told him to punish me, and he spanked my ass. Not playfully, just as hard as he could. It just made me wet. He did it again and again. He stopped when he realised I was just getting turned on.

"Always wanted to fuck one of my teachers," Liv commented.

"He just slipped my panties to one side and started fucking me. He was fairly long and pretty thick. He fucked me really hard and then pulled out and came on my ass. We continued like this for a month. After class, he would fuck me. He liked me to swallow. Then one day he opened his desk drawer and showed me a buttplug he had bought. I hadn't tried any form of anal play until then I was nervous about the idea, but I also was really turned by the power play between us, and I was eager to please him. He made me bend over his desk and inserted it into me. That was as much as we did that time. He told me to wear it in class and during the day. A week after I'd been wearing it for the first time, he fucked me in the ass for the first time. He was gentle, slow, and took his time. He usually fucked me really hard. I liked it, feeling my ass stretching around him. The first couple of times we had anal sex, he was gentle like that and fucked me slowly. Once I was used to he started fucking me a lot harder." Jana told them.

"How long were you in the relationship with him?" Ffion asked her.

"Only a couple of months. I started sleeping with other guys at the college and doing anal with them. I think once the dynamic was no longer fresh for him, he lost interest. It wasn't that much longer after that I transferred here to Somerset. He taught me a lot, but I also outgrew that relationship in the end." Jana answered.

"Hey, I want to know about the guy's experiences," Beddy interjected.

"I'll go first then. I've never had anal sex with a girl. Almost did with a couple of girls, but they got scared." Kieran told them.

"I'll go before Dan. As his story is a lot better than mine. I got stoned with this girl named Steffi a lot. We usually hook up, get high, and fuck. One night she suggested we try anal. We were both really into it, and it felt really good doing it like that while we were high." Randy told them.

Dan was well aware that everyone was staring at him.

"I'll give you a bit of background first. My mom's a fashion designer for a lingerie company. I was home one day. I was either skipping school or I had an actual free day. I was chilling at home watching some TV, and my mom's assistant came round. Claudia is stunning; she is in her early twenties and a really attractive mix of Puerto Rican and Irish. I let her in, slightly annoyed at having my day at home interrupted. I'm just wearing a t-shirt and sweatpants. Claudia tells me my mom has sent her to pick up some samples she had been working on. I told her they were most likely in her office, and she went to find them. She came back a few minutes later holding them, and she asked me which I thought looked best. I was annoyed, so I was being pretty flippant with her, and I said I couldn't really tell I unless I saw them on her. I was expecting some sarcastic reply, but she called my bluff and just said back in a few minutes. She came back in this purple lingerie set. Stockings, garter belt, lace panties and a matching bra. I'm just stood there dumbfounded."

"What did she do?" Beddy asked Dan.

"She smirked at me. Then told me I can see how much you like it. I'd failed to notice that seeing her in the lingerie had given me a raging boner. She walked over to me and started kissing me, and then yanked my sweatpants down. She started playing with my cock. Jerking it at first, and then she started sucking on it. That was some of the best head I've ever had. She wouldn't let me cum and told me to fuck her. We fucked in a couple of positions, missionary, doggy, I loved it when she rode my cock. She came a couple of times, and then she asked me if I had ever tried anal. I confessed that I was big, and any girl I'd suggested it to was too nervous to try. She disappeared off to our bathroom and came back holding this tube of lotion. She covered my cock in it and then told me to work it into her ass. We did it with her riding me. She slowly worked my cock into her ass. The tightness was incredible, the warmth of being buried in her ass. The feeling of her stretching around me. I had to really fight to not cum in her. We had this really incredible slow, anal session. She came twice with me fucking her like that. She eventually let me cum and had me finish in her mouth." Dan told them.

They could also see the massive erection now pressing against Dan's underwear.

"Did you ever fuck her again, Dan?" Liv asked him.

"No, only once. There's this tension between us whenever I see her." Dan answered.

"So fun as these stories have been, we've not had a turn since Liv's last truth. And I know it's my turn. Dare." Jana commented.

"I think we all know Dan needs some relief after telling us that story. Why don't you blow him, Jana?"

"Challenge accepted," Jana replied.

Dan had an eager look on his face. "Can I be greedy, as I've always wanted to experience a blowjob from two girls at once?"