The Wee Hours of Our First Sleepover – Jacob [FM]

The room was dark. It was the first full night that I had slept with Jacob. We were spooning and I had to pee. I slid out from under his arm and made my way to the bathroom. I came back to bed and slid back into my place, nestled up against him and draped his arm back over me.

I re positioned myself and could feel his cock against my ass. I began moving my ass a little and I could feel him getting harder. His hand slid down my thigh and back up and he grabbed my breast and began pinching my nipple between his fingers. He kissed my neck and as his hips began grinding his hardening cock on my backside. I turned to kiss him, but he didn’t allow me to move. His hand moved down to my pussy and I tried again to turn onto my back. He leaned into me and took control. He grabbed and moved my thigh to gain better access to my pussy and slid his finger into me while grinding cock against me. I was completely turned on and tried to resist. He became more forceful which turned me on even more. His hand worked my pussy. Grabbing, pinching, and sliding in and out of me. I began to moan and my breathing picked up. He began to concentrate on my clit. I tried one more time to roll on my back, but he thwarted me again. His hand pinching my pubis and while his finger did circles on my clit. His cock was rock hard sliding between my thighs. He shifted his and I was on my stomach with him on top of me. He leaned in and whispered in my ear that he was going to fuck my tight little pussy raw. I nodded with approval.

A little under the table [MF]ootjob

My college years were some time ago and it feels like I need to start writing out some of these stories if I don’t want to lose the memory of them completely. Every one of these stories is completely true to the best of my recollection. You will know they are true because sometimes what happens to me in these stories is just too ridiculous to be made up.

In my later college years I had an on-campus office job. It was easy work, it paid pretty well, but mostly it was fun to be working in an office setting with primarily older women. In the 1980s, office women wore great outfits, and usually this included blouses with shoulder pads and black pencil skirts with pantyhose. 

Why doesn’t anyone wear pantyhose anymore? Sigh.

Anyway, I’d flirt and joke and generally just be as fun to be around as possible, and the women in my office would sometimes flirt back. Even though I never really dated anyone at work, I managed to cultivate a reputation as a “ladies man,” a rep I can assure you was unearned. One of my roommates at that time worked in the next building over from mine, and he and I would get a group of our coworkers to go out drinking with us on Wednesday nights after work. We would go to our favorite bar, a little blues club near campus that had great dollar beers and potato skins, and usually blow the whole night just listening to music, getting drunk and trying to get lucky. 

I, a straight [M] had my first prostate orgasm a couple of days ago

English is not my first language. But I hope I can make myself understood fairly good.

So here’s the deal, I’m a male in my 20’s who is in a stable relationship with my girlfriend. We do have sex regularly, but never incorporated any anal play into it. My girlfriend is fairly vanilla and doesn’t want to experiment that much. However, I would absolutely love it, and once had a one night stand spit on her finger and ever so gently push it inside me as she sucked my cock. I remeber the orgasm to this day, even though this happened years ago. The way the orgasm kind of started in the stomach region, the way my balls tightened almost to the point that they dissapeared inside me. The ejaculation feeling like multiple orgasms. Her swallowing every single drop as I shot my heavy load in her mouth. And this was without prostate massage mind you.

That time I was handcuffed and dominated by a girl from Tinder (Part 1) [MF] [Femdom] [Bondage] [Teasing]

*Hey all! Long-time reader of autobiographical smut, first-time writer of autobiographical smut. Feel free to comment or message letting me know what you think, whether that’s constructive criticism or just saying it got you mad horny.*

As soon as the door closed she told me, “Take off your clothes and sit on that chair.” I undressed somewhat sheepishly, feeling a little embarrassed – yet excited – about being the only one getting naked, and took my seat. She then got two pairs of handcuffs out of her bag and attached each of my wrists to an arm of the chair; I was secured to the chair, but still able to move my hands relatively freely.

My seductive captor went to her bag to withdraw a small bottle of lube, before walking back to me. “Hold out your hand,” she said, before squirting a generous amount of lube into it. She took a step back, looked me up and down and then, with a satisfied smirk…

“Stroke for me. I want to watch.”

ALWAYS check your [T]oys before using them

*To preface; this post is more funny than sexy; but it was certainly a round of sex education (I’ll see myself out)*

I’ve talked about it before but for those who don’t know; I am INTENSELY multi orgasmic *(just read my post about my orgasm record then you’ll get an idea of how sensitive I am)* and very much a “try anything once” type of person so long as it’s ethical.

About 2 weeks ago, off the command of a friend turned domme, I began getting into long term plugging. I’m trying to get up to 24/7 use but for now the most I managed was about 8-10 hours.

To kick things off though, I (in my infinite wisdom) shoved a dead vibrating plug in. Both my spouse and I struggle with object permanence so this thing had no business being in our arsenal of toys, but I just assumed the battery was dead.

*I was not prepared for the damn thing to turn on*

One of my classier moments at the symphony [FM]

God damn it, I hate how many good sex stories I have with this asshole. I addressed this in my AMA, but I’m not being cute when I say I genuinely hated this man.

He was my boss when I was an intern and then we started officially dating after a few office hookups. However, even though he was ten years older than me, he was an insecure little bitch who didn’t quite know how to handle me.

*I swore off dating other lawyers after him.*

Anyway, one time we went to the symphony. It was one of the few times we genuinely had a nice time beforehand.

First off, I looked beautiful. I still remember that damn red dress and how long I took to actually do my full hair and makeup (I’m usually kind of a mess). He also wore this really hot suit that had me thinking dirty thoughts. Sometimes I forget he was actually hella attractive.

We went to dinner and were both just super giggly and cute. He could be sweet on occasion.

He tells me he used to take all his dates to this restaurant.

[FM] two bulls

Once my master ordered me to tie him up in my flat and told me to call 2 bbc bulls over that he had found over reddit. I was supposed to act as my masters wife. The bulls were supposed to spend a day with me and my master supposed to be tied for the whole day.

The day started with them entering the house. They spanked me and ordered me to bring them drinks. The were extremely dominating from the start. Once i got them the drink. They ordered me to suck them and eventually they fucked my brains out. They made me cum just by sucking my tits and they seemed to like that very much. By lunch they had fucked atleast 4 times each and i had orgasmed 6 times in total.

For lunch they ordered pizza and told me to receive it naked. When i was receiving one of them came behind me. Groped my tits in front of the delivery guy and asked him if he wanted a taste. ( i hadn’t given him any such permission) . He made a bet to the delivery guy that if the delivery guy could make me cum just by sucking my tits he could fuck me aswell. It took him about 20 minutes but he did.

My first time with a black girl [MF] LAST PART

So there I was, with my legs on a chair slouched back as this petite ebony girls mouth was on my cock.
Her lips looked amazing. I was watching them wrapped around my shift as she slowly went up and down. She was twisting her head sideways too and I could see the til as it slid past the inside of her cheek.
She started adding some real suction and I could feel a rush of blood every time she did.
As I put my hand on her head and helped slide it further back, she started grinding on my legs. I had the best view and could see her dress start working it’s way up until I could see the top of her ass.

What I noticed was that sje wasn’t wearing underwear and I could now feel my jeans getting damp.
As I grabbed a handful of her braids, she let out a moan and looked up at me.
I simply nodded towards the big couch in the back of the garage and she came up, letting my cock out of her mouth with a slurp.

Fuck.. I got seduced by my physics student[MF]

I’m an astronomy PhD student (32M) , and about 30% of my time is spent teaching lower level physics classes at the university, most of my students are probably around 18-25 and relatively new at the university. I usually have a very good relationship with my students, I try to help them to study before exams and it’s not uncommon for me to meet them at the student bar and party with them. It has happened before that students have flirted with me, but I have always laughed it off.

But this one girl, this one fucking girl, Sarah, I just couldn’t get her out of my head. I don’t know what it was with her, but it was something that really pushed all my buttons. Whenever I was teaching her class I had to actively force myself to not exclusively make eye contact wit her.

*Was it her looks?* Not sure, she was good looking but nothing out of the ordinary?

*Was it her smile?* Maybe, she did have a great smile and had this ability to smile her eyes when she talked.

*Was it her intellect?* Honestly, might have been the biggest factor, she was extremely smart, social and always showed interest in my research.

Late 30s [Group] NJ – Friend gave me a blowjob while watching a movie with her husband and my wife next to us.

So over the past couple of days I’ve started posting about how my wife’s friend and I established a cuckhold/cuckquean relationship with our spouses. If you’re interested in learning how this came about, you can find the stories on my profile. I’ve enjoyed sharing our experiences with you all more than I expected, and have appreciated the kind words and inquiries from folks over DM and chat. I’m happy to share more (no pics or videos though) or answer questions. Today I wanted to share a story from early in our arrangement when “Emma” (my wife “Sarah’s” friend) gave me a blowjob while our spouses sat on either side of us.

This happened about a week or so after our first encounter with Emma and her husband, “Will”. We had them over one weekday night for what previously was our monthly movie night. Quite a bit had changed in our relationship with them since the last movie night, so my wife and Emma chose something a little steamier than usual, 9 Songs, for us to watch. If you’re not familiar, look it up. Not a particularly good movie, but about half of it is comprised of passionate sex scenes.