[MFF] The time I was fucking a girl, who was wearing a strap-on, and using it to fuck another girl

Long post, been typing this up over quarantine for a while now. Long time reader of the sub but first time posting. Apologies if the story telling is a bit… basic, but it’s the one I want to share.

Back story: I work in IT and travel a lot with work. My job means I’m usually with our companies’ customers for a few days while we get them up and running. I can visit them 3-4 times during the start of a project. Normally I stay in fairly simple hotels and either play games, watch Netflix, or work because IT never works right the first time. Sometimes if I know I have a lot of down time I’ll go on Tinder and I’ve had a few hookups from it but this story is very different.

How I [M] (46) started fucking my teenage daughter’s friend [F] (19)

So my ex-wife and I split years ago after she got busted cheating. Since then, I’ve enjoyed being a single guy who’s comfortable financially and in shape, with a very healthy dating life. My daughter, “Sara,” has always been very supportive (she sorta took my “side” after the divorce).

Sara has this close friend I’ll call “Kristen.” She’s a little on the wild side – dyed hair, elaborate makeup, outfits that I would call “daring.” She’s a sweet girl, not exactly a bad influence, just very uninhibited. Very pretty. They’ve been friends since middle school. Kristen is over at our place a lot, and has always been very friendly with me. I mostly leave the girls to do their thing, unless I’m making dinner (or they do, for all of us) or something.

Last year, I started getting new vibes from Kristen. She got a lot more handsy with me, all giggly and smiley. Asked about who I was dating. When Sara wasn’t looking, I’d catch her giving me lingering looks. Stuff like that. I appreciated but ignored it. She and Sara had just turned 18 a few months prior to that, and I figured they were being silly teenage girls. (Which they were, but still.) That said, I definitely fantasized about Kristen. You would too, if you saw her.

[MFF][M] – Kate and I find out the neighbor’s daughter is a pothead and ran out of weed because of quarantine

As per usual, for new people Kate is 23 and I am 37. We met last year and have been pretty much inseparable since. Kate is very much bi, but I am not. She doesn’t mind finding as many unicorns as she can. Kate is brunette, freckly, with green eyes. Kinda that Evangeline Liliy looks, but slightly bigger breasts. I’ve been documenting our most interesting trysts on this account, so have at ’em.

Except for the buildup, most of the following happened last Wednesday and Thursday…
Kate and I were out for a jog and we ran into our neighbors about six houses down. An older couple in their late 50s, they had a teenage some still at home and a daughter that was supposed to be off at college. The daughter’s name was Rebecca, but the parents called her Becky. She has gone by Bex since going off to college. Bex was home for quarantine, as it was a 2-3 hour drive from the college, but her parents said she’s spent most of that time with her ex-high school bf. The dad really winced at that.

[MM] sleepover gone wild

My sister has many friends in school. She is nice and friendly person. I am in highschool junior . I was 18 . The sister’s friend lets call him sf is a very feminine guy. He hadn’t come out yet and neither had I . He is 19.SF was always sigh and awkward especially around me , i thought he was incredibly sexy as i am mostly into fem guys and girls . He had an incredibly round and a good sized butt , he was a very fair skinned guy and was just a little bit shorter than me. I really didn’t think much of it that time because he was a grade bigger than me and I really didn’t care much.

[mf] Losing my (20) virginity to my friend from high school (21) thanks to quarantine

Quarantine has brought me something good! Sorry its a bit long but the whole experience is engraved in my mind right now! Emmi and I have been good friends since high school. We met through some friends but never got to see each other much since we went to different schools. I always had a bit of a crush on her but never found an opportunity to move forward. She isn’t your typically “hot” girl but she is super cute, a little short, and with strawberry blonde hair cut to her neck. Meanwhile, I’m a taller 5’11, slim, with darker hair (I have plenty of pics on here if you are interested!).

The secret chamber [FFM; BDSM; orgasm control; oral]

“Come on Celine!”, my best friend Elle bragged me, “you have been fucking him with your eyes the whole night. Go ask him!”

She was right, I was undressing him with my eyes all night. Him… Gus…

Gus was my secret, or probably not so secret crush for two months now. I didn’t really know much about him, I knew that he was 29 years old and was a regular at the night club we were in. He always wore black clothes, I had never seen him wear anything else. His black hair and very dark eyes made him even more intimidating. It was probably on purpose to seem unapproachable, as he was alone at the bar today again.

Just as this moment a tall blonde, very hot woman sat beside him, started flirting with him. But she didn’t even stay longer than 20 seconds before dashing off, her cheeks bright pink.

“He doesn’t seem to like company today”, I said and looked at her.

Our friends Martha and Karin looked at us.

“But you wanted to know about his secret chamber!”

FWB Who Turned Out To Be Doing Porn [MF]

Random story: when I was about 23, I used to hang out with this single mom in her early 30s, nasty divorce in progress where he had been banging his secretary and ran off with her. She was broke, delivered packages part-time and juggling child care, but when her daughter was with her husband every other weekend, I’d bring a pizza over and we’d hang out.

She was very pretty, but we didn’t have much of a connection. Nice soccer mom type blond with C or D cups, but she was very vanilla and church-oriented, and honestly, not the brightest bulb in the chandelier. She didn’t want to get emotional anyway, so it worked as a FWB situation. Catch up, watch a movie over pizza and beer, fuck, and go our separate ways.

One weekend, I can tell things are a little different with her, and while we’re hanging out she mentions that she’s been getting hassled by debt collectors. She’s $3,000 in the hole from shopping online too much and her only credit card is maxed out, and it’s true, she’s bought some frivolous crap around the house, but that’s none of my business. It was really indirect and circuitous, but I can see the writing on the wall I’m about to get hit up to help her with money.

[M] [27] [Bi] A New Pleasure

Alright, this was a first for me and it’s pretty short. On mobile and formatting might be off a bit.

Setup: I’m an anal virgin. But for the last couple of years I have slowly started to try some anal play but all I’ve ever done was finger myself in the shower. I have a very sensitive hole and always wanted to go deeper. I have only once massaged my prostate and my breath got quick and I came quickly. I also have a few anal toys never used.

So earlier tonight as I’m showering I do a finger clean, just for some extra cleanliness. It still felt great but I didnt get off as I was pretty tired. After I’m out of the shower and in my room I’m getting pretty excited and decide to get a little dirty. I put on some fetish porn, grab my lube and a cock sleeve and a prostate vibrator.

My thought immediately was that I loosened myself enough that I could get it in me. With a smile I grab a glove and my lube, head down, ass up and I rub the lube on my hole, my finger goes in easily and my cock twitches. It takes a moment but I grab my pspot vibe and I manage to actually get it inside me, making me grin uncontrollably.

[M]y girl[f]riend loves anal now. This is the story of how I turned her into an anal whore.

My name is John and my girlfriends name is Joan, this story is co-written. We’ve been dating for six months and I’ve always wanted to try anal. This is a true story of how I turned my girlfriend into an anal loving whore.
When I first introduced the idea to her, she wasn’t really open to it. I didn’t push for it much after that, but one day she was sold into wanting me to fuck her in the ass.
We were both in her dorm room when it happened. Luckily, her housemates were downstairs.
I started with grinding against her round, tanned ass while reaching around with my hand fingering her pussy. I could tell that she was a little nervous by the way her muscles tensed. I wanted to calm her down by fingering her and sucking her tits. She loves it when I do so, and that is how I get her soaking wet. Once she was soaking wet, I rubbed my cock on her pussy to get her even wetter. But I primarily did this for a lubricant to fuck her ass. Once she was ready and had calmed down, I spit on her asshole and slowly shoved my cock up her ass. She instantly moaned and stated that it was a little bit painful, but felt good. I was surprised because I was expecting her to not like anal at all, but she didn’t just love the sensation, she craved it. After a few minutes passed her pussy was soaking and I had three fingers down her throat choking her. She begged me to go harder, faster, to fuck her asshole as hard as I could. I asked her numerous times if she was okay and if she needed a break, but she was a champ, and wanted me to keep going until I came in her ass.
As time went by, I started to go soft because her asshole was so tight it hurt my cock. I pulled out and started jacking myself off. Joan immediately jumped to the rescue and gave me head! I just about came right there; it was so hot to see my girlfriend sucking my cock after it had just been up her ass. It was like I was living in a dream or experiencing a porno in real life.
As she was sucking me, she looked me in the eye and gave me a look that screamed, “I want more.” So, without even asking her, I spun her around and pushed her facedown into the bed and stuck my cock in her ass again, prone bone.
She was mewling like a cat in heat, and every time I filled her deep with my cock, I could feel that my pelvis was slick with her pussy juice. God damn, it was like a fucking swimming pool down there. I thrust my hips, and each time had her gasping. I could feel her asshole muscles tightening around my cock.
On a whim I told her to turn over onto her back and I continued to fuck her ass in missionary with her ankles propped on my shoulders. She kept moaning “harder” “faster” “All the way in daddy”– I didn’t believe my fucking ears until she reached her hand around and grabbed my ass in a death grip, pulling my hips into her. “Like an animal” she panted. “Fuck my ass like you’re an animal.”
We were going about 15 minutes until I was about ready to come. I told Joan that I was about to come, and she begged me, “Come in my ass, I want to be your little cum dumpster.” I wanted to keep fucking her ass but the thought of coming inside her asshole was too tempting. After bucking my hips a few more times, I shot rope after rope of come up Joan’s asshole. As I pulled out, so did my come and it dripped down her pussy as well.
She collapsed into the mattress, a little embarrassed that it could’ve been dirty down there. Luckily, for the both of us, it wasn’t. After she caught her breath, she turned around, gave me a kiss and said, “Want to go again?”

The Roommates, Part 5 [NSFW]

Our game continued but it was a lot harder for me to talk about where I was from and my favorite foods while Kelly was between my legs with my dick lodged into her throat. After I finished we decided we’d go onto the balcony and have some more mojitos and just enjoy the sunlight. It was day four now of shelter in place and though we were in a salacious sex bubble of our own, we were both starting to feel like we could use some fresh air and vitamin D. Although I was originally the reluctant one between the two of us, I found myself now hoping that Kelly wouldn’t wake up one morning with a change of heart. I didn’t know her well enough yet to know if that was a real possibility.