Tag: Anal

To be clear: I never [F]ucked [M]y stalker

In my early 20s I was a theater actor in my local city. I was in a play with an all male cast so as a straight guy there was no chance for a show-mance there. However, the prop girl was interesting: she had a smoking hot body, super athletic and big boobs. However, she did not have a pretty face and had very outdated 80s hair, but she was definitely intriguing. Let’s call her “Eileen.” She kinda looked like Adam Sandler’s fiancé [Linda](https://www.imdb.com/title/tt0120888/mediaviewer/rm2023817472?ft0=name&fv0=nm0004911&ft1=image_type&fv1=still_frame) in The Wedding Singer.

However, I quickly got the sense Eileen was CRAZY. She used to hit on me relentlessly, as well as my friend Jason who was also in the show. It’s one thing to be aggressive, which is wonderful, but she struck me as obsessive. She used to come up behind me and whisper “I would love to give you a full body massage” during rehearsals and stuff like that while I’m trying to focus. It was awkward. And I knew that if I hooked up with her I’d be in deep with a stalker. SPOILER: like the title says, I did not have sex with my stalker. Read more »

[M]y G[F] found pictures of me playing with my ass

So me and my GF have admitted to each other that she likes some anal stimulation and have bought the right lube, some plugs and some other toys. Occasionally we use them, but she really needs to be in the mood.

Since we started, over the past year(s?) I gained an insatiable curiosity to what anal stimulation feels like. I read a lot about the male prostate and the pleasures it can give. I started slowly with just a finger, but really liked it and soon enough I desired bigger and bigger things. Moving to a small plug, then a bigger one. Then I decided to get a glass anal dildo in the shape of an “icicle” (basically small bulbs stacked on each other, growing in size), with the excuse “it will help us train your ass to take bigger things”. This really did the trick for me and could easily touch my p-spot.

Now, my GF did not know about this, I have mentioned to her that I was interesting in trying anal stimulation as well, but she made it clear that she doesn’t want anything to do with my butt (sadly), thus, I continued on my own. Read more »

The Squirting Roommate [mf] [squirting] [anal] [long]

I’m sitting in my dorm room which I share with a girl named Sophia and she is quite pretty and I have a crush on her and I have a feeling that she also has a crush on me. So I am sitting and doing my homework and she is just sitting on her bed watching some stupid movie and I get annoyed on the fact that I am always doing some kind of work and she’s free all the time. I ask her about this and we talk for a while and after, we both sigh and then she comes over to my desk and starts rubbing my shoulders and this is quite unusual as this never really happens, but I am not complaining to be honest. Then she asks me to come over to her bed to watch Netflix with her, I still have homework and I tell her I just have a little left and I will come after I am done. So I finish my homework as fast as I can, writing something I couldn’t remember I wrote the next day. Read more »

A Welcome Interruption [MF] [MFMF] [FFM] [MMF] [oral] [anal] [DP]

We’d just gotten to our hotel from our date where we couldn’t keep our hands off each other and barely had the door closed before tearing each other’s clothes off. I got on my knees in front of the door and worshiped that cock I love until your knees were weak. You pulled me up, walked me backwards toward the bed, spun me around and bent me over the side of the bed. You dove in eating my pussy and ass like it was your job. You were surprised to find that my ass was still lubricated a bit from playing with my plug before you picked me up.

Just as you got me moaning good there was a knock on the door. You groaned into my ass and yelled “go away.” I slid up and threw on a short, slinky robe and headed for the door. You’d barely gotten covers thrown over you when I threw open the door. A couple, man and woman, were standing there. You didn’t pay attention to what he was wearing but your mouth dropped open when you saw she had on an overcoat, just short enough you could see she was wearing thigh highs. Read more »

First ti[M]e giving head – Exploring [M]y sexuality (bisexual)

Standard apology in advance for typos on mobile. This happened a few years ago and I’ve been dying to explore more ever since.

I was in my early twenties at the time and feeling unusually lonesome after a long, dark winter in Canada. As a tall, daily gym-goer, it wasn’t particularly difficult to attract the attention of women, but for about 6 years prior, I had been thinking about what it would be like to be with another man. The thoughts and fantasies first started coming to me like a snap out of the blue in university while on a trip abroad. I found myself only now asking myself what taboos had held me back in the past, however, and decided to see if Craigslist could help me satiate my desires (back when it still existed).

I put up a fairly timid post asking if there would be any guys around my age who might want to help me explore my curiosity slowly and discretely. I heard back from the usual plethora of thirsty guys but what caught my attention was a young, 19-year-old student home from university who seemed out of my league to the point that I thought it could be a catfish. A little bit like Zack Efron, with a swimmer’s body. After messaging for a week or so and spending nearly the entirety of that time hard in my pants at work, in the car, etc., we decided to meet up on a Saturday after skiing with my friends. Read more »

What the husband doesn’t know won’t hurt him [FM]

Before the stay-at-home order, I [F] worked from home 5 days a week. I was alone from 8:30am-4:30pm and between meetings and deadlines would fuck myself senseless with a array of toys (pussy and ass dildos suctioned to the wall, vibrators, plugs). Since the SAH order, I average getting off maybe 2-3 times a week. This morning I woke up insanely horny so before heading into my home office, I put on my favorite chain nipple clamps (extra tight) and shoved my 3in. metal plug in my ass. My husband just came into my office and we had a 5 minute conversation without him knowing I had toys on and in me.
After he left, I shut and locked the door for a conference call (non-video thankfully), pulled my shirt and bra up and flicked my clamped nipples the entire call.
I have a 2-hour video call tomorrow. I have every intention of putting a huge anal dildo in my ass so I am forced to sit on it during the entire call. Read more »

Personal Work from Home Office Slut [MF]

Personal Work from Home Office Slut

So this week my wife is going to be my personal office slut while I’m working from home.

We have a non-BDSM sub/dom sex life. She’s very submissive and I’m semi-dominant. For example today I had her bring anal lube and a towel. She had a short summer dress and no panties on with above the knee socks. I had her give me a blowjob while I worked and then we fucked with dirty talk that I was going to use her ass all week. It ended with me cumming in her pussy because I couldn’t handle all the dirty talk.

So I’m looking for ideas for what I should command her to do each day.

I will post here each day the results. Thanks!

Soccer MILFS part two: “Devil in a blue dress” [M]FF

So if you read part One of my “Soccer MILFS” adventure, you’ll know that I got EXTREMELY lucky & had one of the best nights of my life. If not, you might want to read it first because this is what happened about two or three months after…

Molly and I ended up dating & we had a good relationship, lots of fun and incredible sex. We developed a cool routine of me going over to her side of town, going to the bar I met her & Sarah at and going back to her place for the incredible sex. She was the first woman I had ever successfully had anal sex with; my ex-wife & I tried but failed because of my size (8.3 inches long and pretty thick, which every woman I’ve ever been with has fuckin LOVED because I can hit spots that have never been hit before. I say this with confidence not cockiness).

Sarah would come up to the bar sometimes & hang out with us and thankfully there was no awkwardness after I had sex with them both at the same time & then individually because of how close the two of them were; they grew up together and shit & were like sisters. It just worked out that way; occasionally, we’d flirt & talk about it but nothing too serious and nothing that would compromise my relationship with Molly. Read more »

My first threesome [MFF]

My first threesome (years ago) was not the blessed experience I was hoping for.

I made the mistake of moving a fwb (PJ) into my apartment. I had a two bedroom, my only roommate just moved and I was just 20 years old. In a year things went a bit sideways and the end of the relationship was visible. She lost her job and was a couple months behind on her half of rent and showing no signs of looking for work. I think she had over evaluated the worth of her cocksucking skills. Not that they were bad, but she was a touch pear shaped, nice breasts but wider hips that she grew in that year. A pale skinned red head ahe had just an average face. She said she loved to please and I took advantage… playing my Sega Genesis, blowjob… home from work, blow job… friends taking too long with their turn on a boardgame, go to her room for a blow job… Read more »