Through high school I had done what most of us do, take what I could get. Oral sex seemed to be a one-way street where I gave it, they tried it, and then told me to just fuck them. The fucking was missionary, them on top, or doggy style as the big finishing move. I was much more open than anyone I was ever with. Me and Ann had sex on the couch once. It was as you would expect, missionary.
This was college. I was lucky enough to live in a large house, with fairly liberal roommates. There was a hot tub in a Gazebo. We lit it with Christmas lights, just the white ones. It was nice enough. The house was out of the way, fairly private, and the usual for parties.
I met Rose on Yahoo Chat. I miss the local section of that chat room. I could chat anonymously with locals. I could private chat, and talk dirty. I met some really fun people in person from the rooms. Rose was the high bar of those.
She was two years older than I was, and had a lot more sexual experience. Things like trying anal, or watching porn and having sex at the same time seemed like bucket list items to me. They were fun to her. She was comfortable. She knew what she was doing. She had done a lot of it before.
Rose was 5’10”. Brown hair. B cup breasts with perfect nipples, but her ass was the star of the show. It formed a heart when she bent over. Her pussy would swell, and she was usually very wet. Speaking of her pussy, it was delicious. She was the first one to ever just sit on my face, something I enjoy to this day.
One day she and I were having the “compatibility talk.” Seeing what each other wanted sexually. We were too young to know the other stuff. Monogamous, open, what we wanted to try. This is a conversation I have always repeated. You learn a lot. I know that I need a certain type to keep me entertained.
Her stuff was easy. Toys. Blindfolds. Handcuffs. Her big thing was that she wanted me to learn to make her squirt. She could do it herself, but no guy had. Easy enough. I always fear the conversation from my side. How do you tell someone that their being spit roasted would be OK. If they wanted to fuck your best friend it is a plus? That you enjoy fucking women in serious relationships.
I started easy, told her that I would love any number of group scenarios. Also, would love to try anal. She chuckled, and asked if that was it. I told her it was. She chuckled, and dropped her pants. “Anal is easy, we need friends for the rest…” Dick instantly hard, throbbing.
I remember getting it in to this day. She puta condom on me, then pulled it off. Lightly coating me in it. She took the condom over her finger, rubbed her ass, then slowly put it in, and pulled it out. “ready, I will lead. You don’t need to just ram that in there…”
My dick is just above normal. Nice head, decent length. I always thought of myself as small. My best friend has a huge dick, and that is really all I had to compare mine to. I knew he was big, but I had no idea being thinner and two inches shorter was good for most women. He is actually just glad when one can take him.
She got on all fours, and guided me in. My favorite feeling is entering for the first time. This time is seared into my mind. A little pressure. I wondered if it would happen as I felt the tiniest pinhole of an opening start. She exhaled, and took me in a little at a time. Just the tip. Pause. Breath. Sliding in another inch. Out a bit, pause, breath, in a little more until it was all the way. I slowly pumped until I was done.
A few weeks later we had some friends over. Brandon was my best friend, Jenn was his eventual wife, and someone I always wanted. She was actually like one of the guys. Cool. We liked her. She could wing man, or talk, hang out, whatever. I was very close with her. Them dating made us all closer.
The night went as usual. Dinner. Hanging out. Movie. Drinking. Hot tub. Brandon forgot their suits. What a dumb fuck.
After a quick debate, we all decided skinny was what was happening. We grabbed full drinks, and departed for the Gazebo. I always had to go first. Take off the top cover keeping the heat in, and all that. This worked to my advantage. Brandon always just stepped over the side. Any girls always used the steps. I always grabbed the lay down spot near the steps. Most jets, best view of them getting in, and jet control.
Tonight, that view was naked. Rose got in, and told me to take a look as Jenn got in. Jen leaned way over making eye contact. Her large breasts hung nicely. She put one leg in, then stood up looking down at me. She said, “what have I done” as she turned around, bent over, and gave me the rear end view of my life. She then just fell forward into her somewhat usual seat in the corner. Brandon got in from the side with minimal incident. He was very drunk.
Rose told me she wanted me to sit on the side. I was a little warm, so I did. She started playing with my dick. Jenn bit her lip. Brandon said OK, and pulled Jenn close. Same room was a fantasy. This was happening.
Rose took me down her throat. Rose gave amazing head. One of the few people I enjoyed it from was her. She slowly raised her hips from the water facing Brandon. Jenn was very sexy, but Rose won the ass department. After a few minutes, I reached back to feel her gorged pussy. This thing was super wet. Dripping.
Jenn had mounted Brandon’s giant cock. I remember watching her position herself high in the water, move a hand down, and slowly sink down. It took about a minute. Once it was in she looked like it was OK, but painful. He looked like he didn’t want to hurt her. I remember Brandon being fixated on Rose’s ass and pussy. She was showing him what I had. I knew it. I loved it.
Rose looked up and asked if I was ready to put on a show. Of fucking course I was. This was my moment. I stood positioning myself behind her swollen, throbbing wet pussy, and guided myself in. She was so wet. It felt like we were using lube. There was no easing in, no slow going. I inserted until I was fully in, and started fucking.
Brandon was just watching at this point. I remember him asking Jenn if he could blow inside her, and her saying no. There was a small, hushed discussion I couldn’t hear, then “Ah, OK…UNNGGGHHH!!!” from him. At this point, He was watching. So was she.
Rose came hard. Her pussy tightened around my cock, and she asked if she was to wet. I learned always say yes to this, because it always leads to anal. She told me to fuck her ass. I had never heard it like that before. She was putting on a show. I remember her saying “for the record, a dick his size will never get my ass” as she pointed at Brandon.
For the first time in my life I was sexually superior to Brandon. I had lasted longer. Not only that, but he was watching me, and Jenn was looking like She was ready for a turn. My smaller dick got anal, his didn’t. His girl wouldn’t even take his cum.
I aligned my head with her asshole. It was pretty well lubed from how wet she was. I rubbed my hand from her pussy to her asshole, it was more than wet enough to spare the necessary lube. As I applied pressure I remember Rose shifting her hips right. I remember wondering what just happened. Did I hurt her? I pulled back a bit.
She leveled her hips. Moved a hand back to her ass cheek, pulling at it. Pushing back on me, and shifting her hips left. I felt her ass open. Left, right, left, right, lef6t, right, then I found myself fully hilted in her ass. “I said fuck my ass” she said. I knew only to start pounding as hard as I could.
I came soon after that. Sitting in the tub she looked pleased. Brandon got out, saying to “carry on” and that he had the spins. Jenn sat for a minute. Rose got out to check on Dan. I remember sitting there with Jenn. I wanted her next. I wanted to cum in every last crevice she could offer, just to come back and use my cum as lube for a second time. I wanted to fuck her like he couldn’t.
She slid over, adjusting the jets to off. Her breast hit my hard cock. She asked what we should do about it…but then I heard Rose. He is sick, where are the blankets…Fuck.
She insisted I get out first. I stood. There was this moment where my hard cock was inches from her face. She smiled, and looked at it, then me. She said she had an idea of how to start with that. Her face said feed me your cock…my conscious said get blankets and a trash can for Brandon.
It later turned out a group sex night had been planned by Rose. Brandon liked fucking drunk, and wanted to be too drunk. Brandon later told me he wished I fucked her, because she kind of held it against him that I hadn’t.
More will follow in later stories.
Tag: Oral
“Breaking” My Girlfriend [MF]
Long time lurker. First time poster.
I’d like to share a story about the best night of sex in my life. It was with my wife (GF at the time). I’m going to try to be as detailed and descriptive is possible.
First a background and description of us. If you want to skip to the good stuff, scroll down to the bold font.
We’ll just call her “Jennifer.” You’ll know why I chose that name in a minute.
We met while I was active duty military and we were long-distance for a while. Within the first year of our relationship, I had to go to Iraq. I ended up there for 5 months (shorter deployments: that’s why you go Air Force).
During my deployment, I was a major gym rat. I went to the gym and lifted 6 days a week, 2 hours (or more sometimes) a day. I was getting pretty cut up. I wanted to look irresistible to Jennifer when I got home. I wanted her to see me and instantly soak her panties. So I absolutely busted my ass for 5 months.
instructions for [m]y wi[f]e
I sent these instructions to my wife last night for when she picks me up at the airport later this week. Tell us what you think!!
I will be driving home from the airport, I’ll explain later.
You have two options for clothing, but with either option you may not wear a bra or panties (you are, however, encouraged to wear pasties) and would prefer heels if possible:
1) You may wear a dress. If you would like to purchase one with my credit card, you may, but are limited to a total of $70.
2) You may wear a shirt, but if you do, a skirt must accompany it. If you need to buy either or both items to accomodate the no-bra rule, the credit card rule from option 1 applies.
You must bring a toy of your choosing. You’ll be pleasuring yourself while I drive us home. At some point during that time, you will provide me oral stimulation.
[m] Finally made her mines after 3 years of standby – GOT CAUGHT [fsub] [oral] [Str8] PART 1
So I liked this girl ever since Freshmen year of high school. Back in the old days she just had this little thing with “sibling friends” which i never understood but somehow i became her “daddy” LOL. I felt lucky asf but also she would always talk to me about her guys and such and eventually i just told her “if you’re gonna be talking bout this all the time, let’s just not talk”… and eventually we faded for about a year until sophomore year. We had french together and i was a fucking class clown LOL, we just made small talks and laughs at time but it was pretty rare. But even though she had a boyfriend i still liked her but was trying to move in and eventually got distracted and found a new girl lols. After a month or 2, they broke up and i was like “ight then”. Last week she hit me up again cause i posted something in facebook and she made small talks about it and it eventually got us ribbons once again. I eventually came out and told her that i’ve been liking her for 3 years and she just asked me to come over to her house. I obliged and went over extremely nervous and excited. She asked me to just talk it through from the beginning to the end with my heart and I did… after that she told me she never saw me that was but that she always wanted me, it’s just that she wouldn’t know how to put it out. After i heard that, i pulled her head and started kissing her and eventually got her on the bed. I then started to take off her shirt BUT THEN she stopped me and told me she was a virgin… i told her “so am i” and proceeded. Once i finally got to take it off, i saw her amazing TITS THAT SHE ALWAYS HID. omg her tits were so amazing but she always hid it :( I then started to suck on it while rubbing my cock against her clit at the same time then took off her bra and her leggings. I turned her around and she was wearing the thing i had a fetish with most… THONGS. I was harder than i ever was my whole life. Her amazing small but perfect ass.. THE GIRL OF MY DREAM WEARING WHAT I HAVE A FETISH WITH :O. I told her that she was fucking amazing and turned her back around and told her to suck my dick. By this time i already had pre cum flowing like crazy. She told me she never sucked dick before and i told her to suck it and play with the head of my dick at the same time because i’m super sensitive down there. She sucked it and hit all the right spots with her tongue! It’s like she was born to do this. She hit all the spots i didn’t even know i was sensitive at. She then started to flick her tongue against my pee hole and i just shot abbot of precum in her mouth. She kept doing this for another 20 minutes. Until we heard….
True Hots of our Lifestyle From the Beginning.
My wife thought it would be cute to start putting stories online about out lifestyle and hookups going back to the day we met. We are now 51/46 and have been “Lifestylers” if you will, for 23+ yrs. Even though we didn’t start swinging regularly until after we were married a few years, we did have some occasional play days prior to then and here is the first of I’m sure more to come.
The First and Second Date
Trying to keep these stories from being too long, I will omit a lot of usual stuff. Everything in these stories is TRUE.
[MF] Fucked the hot crazy girl from my D&D group. [Long, I guess]
Hi hello. 34M here. I am quite the physical specimen. 6’1″, chubby, balding brown hair, brown eyes, thick Drew Carey glasses, thick brown beard. I’m an IT sys admin and I love fantasy and sci-fi stuff. Yes, I’m your classic “neckbeard.”
I do okay on sites like OKCupid, usually with like bookworm chicks or cat ladies, because I’m pretty charming in person somehow, but on a bit of a cold streak. Also, my old D&D group disbanded because one guy moved away, two guys don’t have time because of work/kids, and the rest kind of scattered. So I was looking for a new group when a friend of a friend invited me to join his group. I happily accepted and met Sam!
Sam is a 27M, probably about 5’6, skinny, red hair, green eyes, very hot. Immediately thought she was way too hot to be playing D&D with us basement dwellers. Sat around, got to know everybody. Sam plays a chaotic neutral rogue elf and not really sure if it’s her or “her character” but she 2edgy4me complains about every decision our group makes.
[Fm] Storm [oral] [anal] [fantasy]
“So ye’re really goin’, then?” Storm said with a frown.
“Aye.” Anya said plainly. “Like me father before me, and me brother, and me other brother.”
“And nothin’ I can do can convince ye ta stay?” Storm said, jumping down from the windowsill.
“Nothin’.” Anya said, just as plainly, tossing another pair of boomwool trousers into her sack.
“Are ye sure, nao?” Storm said, slipping up behind her, his breath rolling in like a sea breeze over her back. “There are a lot a’things I do…”
Smiling, Anya could feel his tadger rub against her bare buttocks as his hands wandered up over her toned abs and found their way to her firm tits. He wasn’t the biggest she’d had, but by far the hardest and most eager; certainly the most consistently available.
“If I stayed, what’d we even do?” she said, placing her hand on his. “It innae as if I could shack up with a wharf rat.”
“Why cannae ye?” Storm said, slim fingers circling her nipples.
“Me father tolerates ye because he knows I’m goin’ off to th’Academy.” she explained. “If’n thought fer a moment ye’d have me stay, n’d burn ye to a crisp.”
[FM] Getting fucked by my friend’s childhood friend, with another friend in the same room…[25F/26M]
Quick details: This happened around a year ago. I’m East Asian, about 5’4, petite, small boobs but fairly decent ass for my size. ‘Matt’ is Caucasian, probably around 6’, fairly buff but not intimidatingly muscley.
I met ‘Matt’ on a night out with a group of old-time friends on a warm summer’s evening. We were all drinking in a little alcove area of a bar, and all of us were pretty jolly by the time it was reaching about 10pm, since the bar had a very generous happy hour deal going on.
This was when Matt arrived to join us. Matt was a childhood friend of my friend ‘Daniel’, but that night was the first time I’d ever heard of him, let alone met him in person. He was sitting in the same spot I’d originally been sitting before I’d popped to the bathroom to freshen up a little, and that’s how we got talking. Matt explained that he only knew Daniel and one other person there (there were probably about 10 of us in total), mostly because he had studied outside of the city for university, and had been working abroad in East Asia for 3 years too. He’d only recently arrived back to the city and was finding his feet again as a result.
Enjoyed BBC so much that I can’t [F]uck white men anymore. [MF] [long]
Enjoyed BBC so much that I can’t [F]uck white men anymore. [MF]
This happened in last month. It feels like long time ago but my mind can’t stop thinking the first time I tried BBC. I’m a curvy yet sexy and attractive Asian lady. He is a very young good looking sexy black American guy who recently lost his virginity. I thought he was lying that he lost his virginity over a year ago since he knows ways around women extremely well. He’s a lot younger that I am and I couldn’t help thinking that I could teach him the real fucking experiences were.
I replied his ad on Craiglist looking for unshaved pussy to lick. I sent him my sexy and naked photos. Having sex with huge black cock is my ultimate fantasy. He sent the picture of his hot body and his beautiful huge black cock. When I first saw the photo of his cock, I got wet. I set up our meeting immediately. He was a visitor and he was free that night. I wore mini black skirt and black blouse without bras and panties all day working. When he replied, I was on the way home but decided to go for it. My heart was pounding while driving to his place. I felt like I completely naked when I didn’t wear any underwear. My juice dripped on the seat of my car fantasizing my tight pussy got pounded with that big black cock. How tight and how great I would feel.
Opening Kelly’s Marriage, Part 1 (MF) (Cheat)
Kelly knew it was going to be a long, lonely weekend. Her husband, Darryl, would be away for a weekend conference and would be gone until late Sunday night. She was getting ready for her usual Friday girls night out but even that wouldn’t be the same. Most times she would get home a little inebriated, stumble upstairs, and climb in bed next to him. He would usually be fast asleep by then so she would just snuggle next to his warm body and fall dreamily to sleep.
Tonight, she would come home to an empty house and an empty bed.
She looked forward to going out although she didn’t know the others all that well. Darryl had moved here eighteen months ago for a job opportunity. She had just joined him after the wedding a little over six months ago. The girls were mostly co-workers of Darryl’s that he had introduced her to. This would be her fourth time meeting them at a local bar. Her favorites, Janine and Karen, were about her age, twenty-six, and were single as far as she knew. That had not caused any issues to this point.