Tag: Anal

Sharing is Caring [MFM]

Since my story from last night is doing well on here, I'll share one from a few months back.

My roommate, we'll call him Joe gets around pretty well. He usually has a girlfriend or a friend with benefits for a couple months then ends it and has another girl within a few months. He's probably had 3-4 of these relationships in the 18 months we've roomed together and just as many one night stands. He has the looks to back it up, most women think he is attractive, slim muscular and puts effort into his clothes and appearance. I call him a man whore just to give him shit. I'm the opposite, when I am with a girl its for a few months but, when it ends, it takes me some time find a new FWB or GF. (Sorry if we sound like we are just using women, I actually look for relationship material, he looks for a wet spot.) I have had 4 girlfriends (one would say we were never dating and just FWB but we were a couple), a FWB and as of now 2 hookups (lifetime at 23), on top of that there was this one afternoon, which I don't know how to classify. Read more »

4 MILFs, 12 Holes (The Finale) [Str8, mFFFF, anal, bukkake, oral]

“It’s my last day here” I thought to myself.

I put on my swim trunks and walked to the pool. When I got there, I noticed familiar mounds swimming near the edge of the pool. The women submerged and then came back up, causing the bikini top to clasp around her breasts and nipples, then grabbed her hair to wring out the excess water. This was obviously Mrs. Blondy. I power walked to the side of the pool where she was and jumped into the water. Once under, I swam under her and admired her lower body. Mrs. Blondy’s bikini was so fucking tight. She was practically wearing a g-string with how much her bikini bottom was hugging into her ass crack. She stuck her hand into the back to dig it out but proved ineffective. I rose up behind her when she was about to post up against a side of the pool. I wrapped my body around her and grabbed her breasts from under her bikini top; my cock was poking into her ass crack.

“Oh, my! I know this cock from anywhere!” Mrs. Blondy said with a gasp then changed to a seductive demeanor. “But I don’t think we should do this here. There are too many people” Mrs. Blondy said while looking around. Read more »

My favourite Hookup Part I (M/M) [x/post from /r/bigonewildstories]

By this point I've had a little experience with guys, no anal and hadn't even sucked a cock yet. I met Shawn on gay.com (before it sucked). We hooked up twice, this is the first time. He was 18 and I was around 20.

I won't bore you with the predictable back and forth from messaging back and forth. I will note that Shawn was "curious" and had no experience. He was about 5'9" (inch or so shorter than me), a bit of a husky build and about 5" uncut. [I've given my stat line in other stories but at this point in my life I was a bit shy of 5'11", 175lbs, athletic and 7 1/2" cut]

Anyhow, when it's all said and done Shawn invites me over to his place. It's about 20 minutes or so. When I get there it turns out he's got a basement apartment thing going on and silence is key. We make a little small talk, both of us clearly nervous.

I don't remember who instigated it but we started to kiss. Almost instantly we had our hands on each others package through our pants rubbing what were really already rock hard erections. Read more »

[M/F] Anal play exploration

I asked if she was up for something different and she said yes. I undressed her down to just her panties then went to the closet, bringing a piece of cloth I tied around her eyes. I shoved her on to the bed and pinned her arms down. I tied the rope I already had around a bed post to each wrist and gave each a tug to make sure they were taut. Looking over my work, I saw that she had a smile on her face, inches away from my hard dick, as she tested out the rope.

I climbed down her body with tiny kisses and streaks of my tongue across her body. Biting a shoulder, circling a nipple, and kissing upon each rib. Down, down, down until I felt lace against my tongue. I hooked a couple of into her panties underneath her and pulled them down along with my teeth. She pulled her legs together so that they came off with ease. I pulled them a part hungrily and brought my lips within inches, watching her face as I breathed heavily on her slick pussy. Gliding a finger down from her belly over her clit and down between her lips she quivered and arched into the light pressure, into nothing as I lifted my finger away. Read more »

I am going to perform again at private Vegas sex club

In early September I performed in a live sex show at a private Vegas sex club. I needed money for college and I have to admit, I was curious and cautiously excited about the sex.

You can read about my experience here. https://www.reddit.com/r/gonewildstories/comments/3mwaty/performed_live_porn_at_a_vegas_sex_club_for/

I've been invited back and here was the invite I received from one of the owners at the club. This is happening at the end of the month.

We have an opening for you if you want it. Saturday October 31 $5000 plus tips. We pay for airfare and expenses like before.

Situation: This is in the small room. Father daughter show. You and two men. One is 51, the other is 48. Both fit. You met Joe according to him. He was in the after care room and talked to you about your show. Remember? Mike is the other guy. He's a nice guy. You will like him. Hung like a horse if that matters to you. Internal cum shots required. Anal and DP required. Blow jobs required. Light spanking and hair pulling required. Daddy talk and name calling required. Light bondage possible. Toys possible. We can talk about limits when you get here. Duration 60 – 75 minutes. Read more »

Accidental anal (m/f)

I've been with my girl for more than ten years and had always been disappointed at her unwillingness to take my cock in her ass. I've always been an ass enthusiast and hers is a particularly lovely, big round firm one with a cute rosebud so you can imagine my disappointment. It was an ass that needed my cock in it.

The most I was allowed to do was rub my cock against her rosebud a little to get myself excited before fucking her pussy.

One night we were playing with massages and I was enjoying the view of her on her stomach with that amazing ass tempting me. As I applied more and more massage oil, I cheekily let some ooze between her ass cheeks each time. I saw her move her ass a little as the oil dribbled onto her rosebud but she said nothing; obviously enjoying having her back, neck and shoulders massaged.

I alternated between rubbing oil into her back, and massaging her neck and shoulders while cheekily also rubbing my cock between her ass cheeks. I'd been sneakily oiling my cock as well while oiling my hands so it was gliding between her cheeks nicely. Read more »

4 MILFs, 12 Holes (Part. 2) [Str8, mFF, anal, cuck, oral]

I walked out of my hotel room holding Mrs. Done's room key. The comfort level in my pants were dropping the more and more I thought about the things I was going to do with her. Her room was the same one that all of the MILfs met me in, so I already knew where I was headed. The keypad lit up green as the door un-locked and I let myself in. I was greeted to the beautiful sight of Mrs. Done with her legs spread apart and completely naked; she must have fallen asleep like this. A purple dildo laid near the bed, it probably fell off. Mrs. Done shifted around on her bed, spreading her legs even further apart making her pose look like a frog ready to jump. I walked over to her and stood over her sleeping body. She writhed in a little pleasure after I poked her left breast. Her suitcase that was across the room suddenly fell over. As I picked it up, I noticed rope in her suitcase. Mrs. Done must have really wanted to get freaky on this fuckcation. I grabbed the ropes and began to tie Mrs. Done's wrists and ankles to the bed frame pillars. Mrs. Done woke up after I was done tying her up. Read more »

The Camp Counselor Gets Gangbanged [fmmmmm][oral][anal][blkmail][Str8]

It was the summer after my sophomore year in college and I decided that I wanted to spend it helping out at a local camp. I always loved summer camp when I was younger. I had gone for years until I graduated from high school and I really missed the atmosphere of it all. A friend of the family said he knew of a camp close to home that was looking for one more counselor and he would have them give me a call. I answered the phone that evening and found myself in an unplanned phone interview. Because our family friend had recommended me, and they were pretty desperate since camp was about to start, I was hired. Camp started the following Monday. When I showed up that morning I was a little surprised. I guess I should have inquired more about the type of camp that I would be working for, but I was so excited to get the position, I completely forgot to ask. There were guys everywhere. Not just guys, but football players. I enjoyed watching football, but I didn’t know enough to do any kind of counseling on it. I told this to my boss as he introduced himself. He said that it would be okay, I wasn’t needed for that. I was in charge of just keeping everyone quiet and in line when necessary and if there was any kind of issues that arose, they may need a female to talk to. I guess that made sense, so I stopped worrying. Read more »

4 MILFs, 12 holes (Part. 1) [Str8, mF, anal, oral]

"This is going to be fun", I thought to myself while looking around the check-in area at the hotel. The door to the lobby swung open and four very shapely women walked in with suitcases. I recognized all of them except one.

  • Mrs. Blondy: an extremely busty, blonde, round tight assed, in her early thirties, 5'7'' stay at home mom with her kids already in college. She was wearing an elegant tight white dress that hugged every crevice of her body with heels.

  • Mrs. Done: a MILF in her early thirties, standing 5'3'' with watermelon sized breasts, an ass the size of two medicine balls, black hair that went down to her shoulders, and a very thick Chinese accent. She was wearing a tight green dress and heels. Her panty outline made it look like her dress was a plastic bag vacuumed around two basketballs with half of an hourglass in the middle. Read more »

What it’s like to have your best friend help you out of jeans two-sizes-too-small and fuck him right after. (F/M)

Another week-late post and I don’t even know if my grammar is right in most of the parts but brace yourselves for another long one!!

Mark's grandma died Wednesday, September 30, and he's been feeling pretty down about it all. It hurts to see him that way. The guy's my best friend. He's always, always laughing; he laughs when he's making fun of himself, he laughs when he runs, he laughs when he's in class, he laughs even during sex. When you listen to his voice it's like he has a permanent laugh in it. But he wasn't like that this week.

Here's another thing you should know about Mark: he has (had) only one grandparent left alive, and that was his grandma on his dad's side. He never met the other three. Both his parents are doctors. Both surgeons. Both still working despite their old age. Mark has five older brothers and one younger sister – all of them were pretty much raised by his grandma. If you check his phone, most of the time he’s texting his family, his grandma especially. Read more »