Broadening a young bride’s horizons [MF] [Long]

Disclaimer: this is way too long, but maybe someone will enjoy. Fun to remember and talk about either way. I’ve needed to tell this story for a long time.

This happened a long time ago, in the Jurassic days of the internet before phones or dating/hookup sites. I was fairly active on IRC, or what the n00bs called chat rooms. Lots of sexting occurred, although they of course didn’t call it that, a fair bit of pic sharing despite people not having phones with cameras and needing to suffer through dial-up speeds, and plenty of more casual flirting to pass the time. I was a regular (and part time moderator) of a channel dedicated to a non-stop game of virtual truth-or-dare. The truth part is pretty self-explanatory, but the dare part mostly revolved around embarrassing public displays in the more serious channels, which would often result in a temporary ban. Other times the dare might be to engage in some kind of sexual scenario with another more-or-less willing participant, all typed out sexting style, out in the open for the enjoyment of all. You get the idea.

My roommates mom and I . Part 1 [MF]

I got out of a pretty bad relationship a few months ago. My ex moved out and my girl best friend, Airin moved in. We’ve known each other since high school and I was there for her when she came out as a lesbian to our friends and family. Basically we’re like annoying siblings to each other and always had each others back.

Lately though, her mom’s been coming over to our apartment more to spend time with her. It doesn’t bother me much, her mom pretty much raised me too so I was used to it. I should mention miss Lisa was always really attractive. She had short black hair, a yoga instructor body and an ass out of this world. Every now and then I’m sure she saw me staring at her chest or butt during my teenage years. The looks increased the more I saw her.

At The Pool [D/s] [Mf]

My only completely true story… so far. About my introduction to submission and kink.

Have my vodka and lemonade, flouncy skirt on with my bikini top, and walk down to the pool, remembering all my times with Him at his pool, hoping to see someone who will see me for the submissive sex-crazed slut I am…like he did.

1. The first pool party after he claimed me, he snuck into the bathroom with me. Get undressed, he commanded. What?! In front of you? Yes, he said. And I did, wondering amazedly at my willingness to do this… so far we had only had a kiss or two, furtive groping under the table at dinners… He sighed, so happily, at seeing my ass, naked at last.

2. Later, “accidentally” alone in his garage, he bent his tall frame down to kiss me and slipped his hand quickly past the waistband of my stretchy tight skirt, straight under my thong, and pressed his finger against my asshole. I yelped and leaped away like a startled rabbit… now I long for that moment, wishing I had pushed against him, inviting him into my welcoming ass.

My [M] one and only massage by a [M], unexpected. (Really happened, a bit long)

I was just over 30 at the time, unattached and often went to different massage places. This was way back before the State of Oregon decided to legislate the massage profession, so it wasn’t really that difficult to find a woman willing to do a happy ending. In fact, most places had a receptionist out front that told you the rates and how much it was with a “hand finish.”

That actually was nice, a single guy could get the edge off without having to go through all of the wine and dine stuff. There was one place in south Portland I really preferred, it was clean, they had showers, and the price was right so if a guy struck out on an evening’s hunt for a one nighter, stopping off on the way home was a sure thing. I was young and in shape, had a few bucks in my pocket so usually I could find a friend in one of the clubs, but this night I was having no luck at all, so around 2 in the morning I drove down. The place was always open, I never saw it ever closed. Those of you that knew Portland back then will know about it, it was named after the creek nearby, same as the road it was on. The first thing I noticed was the parking lot in the back was full, I had to park down the street. I knew they usually had 3 or 4 girls on staff so it shouldn’t be a problem waiting, a few times before I had a short wait.

Breakfast (Spying On My Sister, Part 2)

Jenna and James came up the stairs for breakfast in the morning. I was already on the counter drinking coffee and having toast. James just had on boxers, exposing his chest, which wasn’t muscular, but toned so you could see the outlines of his build. He was hairless for the most part. He wasn’t hot but he was definitely sexy. Jenna, I’m pretty sure, had on just an old school “Weezer” t-shirt; one of James’, no doubt. No bottoms, but the t shirt did go to her thighs. They both had nice bodies and were comfortable walking around like that. The main reason they walked around basically naked was easy access.

My sister and her boyfriend had an added bonus this week. Our parents were in Hawaii. We had the house to ourselves, which meant James was living there that week. And they were fucking a lot. It was like they were each other’s newly discovered drugs and they were on a binge. I could hear them every night; they were as loud as they could be, knowing they had no one who’d tell them to cut it out or keep it down. They knew I wouldn’t.

Fucked a virgin [MF] while her friend [F] spied on us

First, thanks for all the support for the last story. Gives me confidence to post more. And so…

I dated this girl for a short while in university. My friends all hated her, but I thought she was cute. Redhead. Perky little tits. Skinny. She had this vibe like she might turn out to be a lesbian.

But I was the lucky chap who got to take her virginity. 

We’d been fooling around for a few months, lots of sucking and licking, jerking and fingering. 

Full sex never really seemed on the cards for some reason, but it didn’t really matter because she could suck like a fucking goddess. And she was happy to swallow gallons of cum too.

She’d tell me about the various objects she’d shoved up her meaty little pussy. Her little vibrator, vegetables, a bottle or two (always in the bath, so it was nice and warm, of course). So I was surprised she still had a hymen. 

She’d also ask me about the girls I’d fucked in the past – I loved telling her those stories because she’d get really turned on and it would always end with me squirting cum down her throat.

His Daughter’s Friend is Trouble [Mf]

This summer at the lake house was supposed to be time for Marc to bond with his estranged teenage daughter, Emily. But Emily brought a friend, an internet bikini babe named Cat who turned his idyllic vacation into a living nightmare. The nineteen year old blonde sauntered around his lake house in skimpy bikinis, teasing Marc with her great tits and a peachy ass. He had already caught her giving a blow job to the pizza delivery guy and wondered if she was having lesbian sex with his seventeen year old daughter. Then he made the worst mistake of his life and drunkenly gave into Cat’s sexual advances. He laid in bed worrying what the vixen will do next.

Marc was nearly asleep when he heard his door creak open. Dressed in a t-shirt and panties, Cat walked into his room. Her blonde hair shimmered in the moonlight.

“What?” he whispered.

“Let’s do it again,” she said, crawling in beside him. “Let’s fuck.”

She kissed him with her pink pouty lips which ignited the fire in his loins. He took her eager body into his arms, becoming lost in the sensation of the warm young flesh rubbing against him. He stopped when he thought about Emily walking in. He got out of bed, grabbing Cat by the hand.

My big stepsister takes care of me for the first time [FFM] [first person]

Katie was the best step-sister I could have ever hoped for. She was five years older than me so she was great at helping me with homework, giving me advice about high school, and helping me apply to college. She even gave me advice about girls, since she was bi and dated a lot of women. I couldn’t have asked for anything more in a big sister. I always looked up to her.

We kept in touch after I moved halfway across the country for college. But with her starting work and me busy with school, we weren’t super close. After I graduated college as an aimless English major making up my plans for work as I went along, Katie offered me the second bedroom in her condo rent free.

Partners in crime [MFF]

I met Dana in college in one of the classes we had together. We have a lot in common and get along well. We have a similar taste for bad humor, another thing we got in common is our love for women. Dana was attracted to women only, so too bad for me. But that didnt stop us from becoming friends.

It was new for me, i never had a lesbian friend before. Her being lesbian is no big deal of course but it was cool for me to hear the female perspective of hooking up with women. I loved to hear her stories, not to jerk off when i got home but because is was genuinely interested in what she had to say. We are both very experimental and open minded when it comes to sex.

Infact it was maybe even easier to be friends because there was no sexual tension at all. We had both seen each other naked and had pissed together too when we were out. She joked about my dick being small but i guess i am more of a grower than a shower. Dana is very feminine but has a strong thick body with modest b-size breasts. I adored her full bush which she said was natural but looked well manicured. She is an attractive young women, but i didnt look at her in that way.