Tag: Anal

My third time with Gwen and Steve. [MMF] [MFM]

It's been two years since I've been with them, but I realized I never documented our third and final time together, and I wanted to be sure to do that before the memories were lost for good. See my submission history for the rest of the saga.

Our third and final encounter took place one week after the second time. We were all really enjoying each other, and couldn't wait for more. Gwen had been texting me all week, sending naughty pictures and doing everything she could to get me into a frenzy. This proved to be very successful. She told me she had something special planned, but would say nothing more, nor offer any hint. My senses were on high alert.

When she opened the door to let me in that night, she was wearing nothing but a black lace bra and matching panties. She pulled me inside by my jacket without a word and dropped to her knees. Without a sound she worked my jeans down to my ankles and swallowed my cock to the hilt. This was a new form of greeting that I could get used to. She cupped my balls in her hand and slowly bobbed her head up and down on my shaft, soaking it. One by one she gently sucked each testicle into her soft warm mouth and rolled her tongue over it, swirling. Then without warning she stood up, gave me a sexy grin, grabbed my cock firmly in her hand and led me into the bedroom. Read more »

Lunch Break Fun

Long time lurker here. I enjoy reading all your stories and decided today is a day if any to tell you my story. This literally happened yesterday, but to start off a little about myself. I'm a 26 year old black male, about 5'10, athletic- lean build. I'm avid gym-goer, Crossfit being my torture of choice. I've been told I'm blessed below the belt (surprise, surprise!). Not for my length though, it’s for my girth. I would assume I’m about 6"-7" but I can get pretty thick when blood rushes to my member.

Anyway, I've been talking to this girl from FetLife for a couple of months now, let’s call her Kay. She’s Caucasian, about 5'3", short blonde hair, with a tint of Lavender. She has a full figure which she holds very well, D or Double D tits with a nice bubble butt which is held up by a gorgeous set of thighs that I have ever seen.

I don't know if anyone else has noticed but lately white girls have been giving ethnic girls a run for their money. Read more »

The first time I lost my anal virginity on a sketchy craigslist hookup [m/m]

I'm bisexual. But in the weird way where I only want to date girls, but occasionally I really want to be fucked by a guy. And by that I mean I want to have a guy rip of my clothes, call me a slut, throw me on the bed after forcing my mouth on his cock, and plunge himself right into my ass without asking anything about what I want. When it comes to men, I just want to submit, get fucked, and be abused.

I had this itch a few months ago, which led to me going on Craigslist and responding to someone's ad. He was tall, athletic, half asian, and looking for someone to drop a hot load in. As for me, I'm half Korean/Caucasian, athletic build, long dark hair, with a nice smile. People tell me I'm really good looking, so let's just go with that. Read more »

The first ti(M)e I (F)ucked a married girl. And some anal! Detailed, true.

This was many years ago so please understand as it will hard to be as detailed as I usually like to be. Also this incident takes place about two years after my sexcapades with a very hot older lady, which I've written down for you arousal HERE. The married woman is Amber, my friend Kevin's wife…

Her husband overseas at work for an extended period, Amber had just moved into a rental home. Since there was no real male figure in her immediate life to help, it fell on me to be a good friend and do what I could for her. It was also a bonus that there was an abundance of Jack Daniels and good bud to be had in exchange for me just helping unpack, move furniture, yard care, stuff like that. Plus we were good friends and had a lot of fun and goofiness together. Read more »

Beach meet [M] [CD/Trans] [oral] [anal]

First post here. I'm using one of my stories penned under my tranny email address. Comments welcome.

Penny loved the cool summer breeze coming in off the shore as she walked along the French beach, back to her apartment; her open toed shoes in hand, her feet immersed in the golden sand. She was to leave here tomorrow, and started to think about what a great holiday she'd had — no life romances, but certainly no shortage of hot studs. This was a beach that had given her a number of those studs, and she wanted one final holiday fling before the reality of home and real life inevitably returned.

As she walked along, Penny could hear muffled moans of pleasure from behind some of the dunes at the edge of the beach; not terribly discreet perhaps, but everyone knew the kind of action to expect on this beach. As she continued along, towards the apartment complex, she noticed him coming out of the water in front of her . Read more »

First time anal play [f]

The door closed and he pulled me in closer. He smells incredible -the scent is soft, like a bar of milk-white soap, but with the undertone of his musk. I inhale and crave him. His fingers run up through my dark hair near the nape of my neck. I grasp his shirt. All I want is him. I can't help that my hands run down to his belt. I notice my breath becomes deeper as his lips graze mine. His hands travel down my back and to my plumb firm butt, (I pride myself on my squats), and he simultaneously squeezes and pulls me into his hips.

Both of us are in jeans, and his pants are haphazardly undone -belt, button and zipper. Shirts have been done away with by now. My eyes are drawn to the contours of his arms and shoulders. Before you know it, we're in bed. I'm sitting on top of him in my lacy bra I lean over and kiss him. His stubble from the day is rough on my skin, but I find it oddly invigorating. I tease his earlobe in my mouth. Between my lips and licks I'm sure he can hear my satisfactory exhale. He grabs onto my thighs in affirmation. Kissing becomes intense and I feel my face start to flush. My panties are beyond wet. Read more »

More with James

James and I pretended like nothing happened for a week or so. He did mention he wanted to have more sex with chicks. I figured the mutual oral while fun was a one time deal. One night finds us both off work and insanely bored. He invites me to his dorm to hang out and likely play some games. Im quite inebriated and horny when I make my way to his room. Hes laying on the bed in just shorts watching a movie. I sit in the desk chair. A very awkward 15 or so minutes go by. We both know we want to fool around. I decide to make the move first and lay down next to him in the bed. Im in shorts, tee, and socks. Within moments we are intertwined on the bed watching the movie. He takes it further and slides a hand under my shorts and boxers to slowly jerk my cock. Our shorts and boxers are both off shortly after that as we furiously kiss and our hands jerk each other. James climbs on top of me and starts thrusting his dick against mine. I get him to stop by motioning for him to bring his cock to my mouth. He slides it in and I start sucking him off. He really seems to be enjoying this. I start playing with his smooth nutsacks. He goes crazy for it so I decide to take it further. I suck on one ball before moving to the other as I stroke his cock. James really gets into it. Debating my next move, I decided to just get him to cum. He had other ideas. He moves off my chest and begins rubbing his hands around my crotch. He gets me even more turned on. He takes a lot of my cock at once into his mouth while staring into my eyes. I begin to fuck his mouth as he tries his hardest to do a lot better than his pretty good first time. This goes on for a few very passionate moments. He gives me a definate look. I stop. "Are you-" "Yes. Im sure." I had never done anal, either with a guy or girl. I had never recieved, either. Now, James wants me to do it to him? Or was he wanting to fuck me? James grabbed a box of condoms from his nightstand. He pulled one out. This was the moment of truth. He smiles as he opens it. He starts sucking my cock head again. I close my eyes to enjoy the moment more. I feel a rubbery finger at my hole. It presses in. He slowly gets his finger in and presses it in further. It feels so weird to me. James starts focusing on the anal pen and moves his finger in and out. He puts a second finger in the condom after about five minutes and gets it situated as well. Im not hating this nor loving it. Its ok. A few moments more sees a third finger. Then I feel him hit a great spot just right. I had heard of someone talk about the prostate before. Experience is much better. I let him know hes at a good spot. He keeps hitting it just right as I feel an intense orgasm brewing. James figured this out and stopped. Grabbing a new condom, he places it on his cock, lubes it, and pushes his head right against my hole. The angle is weird so I get on all fours. This works much better as I feel him enter me. It took about a minute for him to get in and start to pound away. It felt really weird to feel a cock in me but not bad. James goes wild and doesnt last overly long. He collapses on my back. I really want to fuck something and James seems out of it now. He falls onto the bed and passes out. I grab the nearest set of shorts and boxers and head towards this girls room. I obnoxiously knock on the door till she opens up. She refuses to let me in since her roommates hated me. I tell her I just want to fuck. Meg says fine lets go. I reach in the pocket to grab the room key. Its not in the right pocket. I find it in the left with James ID. She laughs as she figures out Im in his shorts somehow. We go to James room and start kissing and stripping. Hes passed out on the bed still naked. We wake him up and he just goes to chair. He watches as Meg starts blowing the same dick he had earlier. She gets me nice and hard then sits on my face. I loved her taste. Meg is the best tasting chick Ive ever been with. She slides onto my dick and we start fucking hard. Everytime she goes down I slam up. We go for a while until I flip her over and start fucking her doggy. For some reason having James as an audience made us really go at it. We switch to missionary when her knees started aching from the super uncomfy dorm bed. I didnt last long in the new position and cum hard. It was an amazing orgasm after the work up earlier and the amazing sex. Meg asks James if he wants a turn. He jumps at the chance almost literally. He hurries into the now crowded bed and slides his cock right in her. He looks estatic as he is in a vagina again but with no condom this time. He doesnt even seem bothered by the fact I dumped gallons of my own cum in her. I cheer him on as he fucks her missionary. He is still unpracticed and it shows as he goes for the gold in the fuck race. She tells him to calm down and focus on deep thrusts and not a lot of quick ones. He is in a different world as he keeps fucking her hard and quick. I had gotten her to a decent, not mindblowing, orgasm. James had no concern for her pleasure as he humped for his life. She gets him to lay down now next to me instead of her. She begins to ride him to her pace. She stops him from thrusting up with each down thrust on her part. Im rockhard again watching. Meg begins jerking me as she rides James. "Id love to see two guys kiss. Itd be like guys seeing lesbians kiss." This was beyond anything he and I had done and seemed like a weird barrier. We pressed in close towards each other. His blue eyes are inviting as our lips awkwardly touched. Soon we were kissing passionately. Meg is riding him with enthusiasm and cheering us on. "Oh fuck!" Shes really surprised by his joining in of jerking my cock. She watches and rides him as he and I kiss as he jerks me. Her face twists into an orgasm as she stops paying attention to anything but her pleasure. James groans as she cums. He also loses attention and once again seems board stiff. She lays on top of us smiling. "Both of you jizzed in me. Nasty boys." We all curl up and fall asleep. Read more »

My [F]riend’s first gangbang [MMMMMMMM] during spring break as told to me.

This was told to me by a lover of a gangbang she had when she was younger. Please take into account this was told to me about 10 yrs ago of an event that happened 10 years previously. I'm straining my excellent memory to remember the details and questions I asked about that day. For science of course.

where did this conversation take place? our first meeting at a gangbang i was hosting from Craigslist. go fig.

my friend at the time was a fairly curvy 19 yr old of Philippino decent with big, DD tits and was mentioned prominently in an entry on my blog.

she went on spring break with a few friends and somehow got separated at a hotel they were staying at. From what she told me she was perpetually horny at this age and was basically a slut in college, and obviously later in life.

Anyway, she wound up in a room with about 8 guys or so playing drinking games. The conversation eventually turned towards sex and there were a number of guys she was interested in, and considering she didn't like to drink much, she was quite sober in her decisions, but drank just enough to blame it on being drunk. Read more »

My very own MILF (M/F) (long)

I enjoyed writing about my 1st m/m experience yesterday, but here's something more recent with a MILF that is definitely one of the sexiest life experiences I've had the joy of taking part in.

This story took place late last June. I work in a pretty typical office, a 9-5 job, but on this particular Friday evening last June I was working a bit late. We had a fairly large project that needed to be wrapped up, and it was almost 7pm by the time my workday ended. My friend Tom also works there, and after we finished up for the day we decided to head down the street to our regular pub to wind down.

The pub isn't anything fancy, but is where those that enjoy a pint or 2 in my office go to get their fill. It has barstools, tables along the wall, and a fair sized open floor that is either filled with tables or cleared as a dance floor. There are also some dart boards along one wall, and a back patio. On a typical Friday evening it would be half full, mostly filled with locals that live or work nearby. On this particular night, though, it was packed and the place was hopping! Tom and I arrived around 7pm expecting it to be a typical evening, but it turned out to be anything but. Read more »

My Mexican (F)riend is a sub (LONG)

This is my first story, so please offer criticisms. I am a white, blue-eyed guy with a great smile. I am 22, 5'11 and weigh 170 lbs, at 14% body fat.

The first day of my Religions class (middle of January) I walk in and see her. An old friend I used to party with, but hadn't heard from in two years. Jessica's black, around my height, with a phenomenal ass. The kind that is just big enough without reaching gargantuan proportions. I sit next to her and we catch up over the course of the next couple class periods. After reigniting our friendship I notice someone else.

She is 5'1, 105 lbs, of pure Mexican beauty. Her beautiful brown hair looks as if it were finessed by the people who assist models. Her luscious lips accentuated by her red lipstick, standing in contrast to her light brown skin. In the beginning of February I sit next to her. My heart is beating rapidly. This is something new. Somehow, even though my heart was acting as a snare drum inside my chest, I play it cool and get her number and name, Selena. Read more »