Well, it finally happened. At 27 years old and after years of having the urge to mess around with another guy, I finally worked up the courage to see it through last weekend. My first time wasn't your traditional first time. I was looking for a something specific. I am an athletic and muscular… in short, I am a jock. Very straight acting with a girlfriend, and you would never guess I had this side to me. When it comes to guys, I am not attracted to other guys like me. I am attracted to skinny nerds who are shy and timid. Now, you're probably thinking this is because I'm a jock and I want to manhandle and have my way with a guy smaller than me, but that assumption would be wrong. In fact it's quite the opposite. I had a strong desire to be fucked, manhandled and humiliated by a scrawny guy. I had fucked myself with toys many times but obviously never experienced a real cock. On to the story. After many hours on Grindr, I wasn't finding what I was looking for so I reluctantly created an ad on Craiglist. I said I was looking for a" skinny nerd type" who may have gotten picked on in high school and wanted to take it out on a jock. I posted a picture of my athletic body and muscular bubble butt. I obviously received a TON of responses from interested guys, but only two that really fit what I was looking for. They both sent me some pics and I emailed back and forth a bit with both of them and eventually we chatted on the phone. They both seemed like normal guys but one really interested me more than the other. When I talked to him on the phone he was very quiet and reserved. He was a pre-med student at the local university an said he tutored other students in his classes. He also said he was on a "math team" in high school. Bingo. This was the guy. He said he lived by himself so I could come over there. Obviously it's pretty sketchy to meet someone from craigslist at their place, but this guy really didn't seem threatening or dangerous so I agreed. Like I said, I've never been with a guy before so I quickly cleaned out my asshole as best as I could, grabbed some condoms and flew out the door. I didn't know if he would actually fuck me but I wanted to be prepared. He lived in a typical university apartment complex with a bunch of drunk kids running around. I knocked on the door and the cutest, nerdy looking guy I've ever seen answered the door. He was short and looked to be only about 5'4'' or so. He had on glasses, which is a major weakness for me. I could see how this kid may have gotten picked on quite a bit by guys like me. We sat down on his couch had a some beers and chatted for about 15 minutes to warm up to each other. He had a PS4 so we played Halo for a bit (he was good). I could tell he was getting fidgety and my cock was hard the moment I walked in the door, so I scooted over to him on the couch and started to kiss his neck. Remember, this was my first time so I was pretty clueless about what I was doing, I just knew I had to do something because he was to shy to get it started. I never had the desire to actually kiss a guy, but we began passionately kissing and all those thoughts went out the door. He stopped kissing me and quietly said, "suck my cock." I didn't say a word. I just dropped to my knees in front of him, unzipped his pants and released his cock. Now, I've seen a lot of dicks in gym showers throughout my life but this was the biggest one I had ever seen. It was really disproportionate with the rest of his body and had to have been about 9 inches long. I muttered "fuck…" under my breath and he let out a giggle. I took the dive and put him in my mouth, tasting the sweet pre-cum oozing out. Being my first time sucking a dick, I gagged more than I thought was possible. He didn't seem to care and began to forcefully shove his dick down my throat. I was vomiting on his dick but he kept it going. I thought, "is this a dream?" He was really taking his aggression out on me. He slipped his dick out of my mouth and walked to the middle of his living room. He stripped off his clothes and beckoned me over. I told him I was having second thoughts because he was so big and I had never taken anything that big inside of me He just said "get over here and lay on your back" in his tiny high pitched voice. I obliged. I took off my clothes and laid on the floor in front of him. I told him I had condoms but he said he was clean and didn't want to use those. I believed him (and the condoms wouldn't have fit him anyways). He lubed up his dick and my asshole and lifted my legs in the air. I thought with the aggression he was exhibiting he was going to ram it in as hard as he could so I braced myself. Instead he eased inside of me until my hole was relaxed and ready to take it all. After a few minutes he began to work it faster and faster until he was pounding me real good. I was already loving what was happening to me so wasn't expecting much more, but all of a sudden I saw some rage come over him and he started to slap my face and chest. I exclaimed "fuck yeah" and he told me "you're not supposed to enjoy this you asshole." He spit in my face and slapped me again. I was in heaven. He fucked me good for another 10 minutes or so before blowing his load inside of me. I had never felt that sensation before but now I think I'm addicted. He pulled out and laid beside me exhausted. I was jerking off this entire time and blew my load all over my stomach not long after he finished. He was suddenly back to his shy self and quickly put on his clothes and said, "thanks." I followed his lead and put on my clothes. He said, "thanks for coming over. We'll have to do it some other time." I just nodded and walked out the door a happy man. Pretty good for my first time.
Tag: Straight
Sayonara Sweetheart!
So I am in this public restroom at an interstate gas station, taking a leak, when I read the following handwritten note on the wall: "Lonely, hot Asian Waif willing to suck big American white guy dry! Just text me at xxx-xxx-xxxx and I will be there in 30 minutes driving a yellow Mustang. /s/ Sayonara Sweetheart". I omitted the real number for obvious reasons.
"Shit, I got some time to kill. Why not?", I thought. It was already late and I was on a long trip and about ready to check into a little hotel down the road for the night. So I sent a text to the number saying I was interested. In about 5 minutes I got my reply! "On my way, big guy! Get ready to have your mind blown!", was the reply. Hot damn!
30 minutes passed. I was on my 3rd smoke in the parking lot and getting ready to leave. What the fuck was I doing? This is crazy! Then as I was ready to leave a bright yellow Mustang wheeled into the parking lot. "Alrighty-oh! Here we go!", I thought!
Daughter’s bff and I
I’m Bruce, I am 36 and work as a General Building Contractor. I was married to my high-school sweetheart. We married in high school. It takes about 6 months for a divorce to finalize and today is 6 months. Marriage is hard. Our twins are in 'The city' at 1st year college. We were renting and had a beat-up old car. My wife (x-wife?) has a nice job so she didn’t ask for anything. I moved out and rented a small 2 bedroom house about 6 blocks away. I let the twins know that they could come any time no matter what. I really didn’t have much to move so the house is for the most part empty. It had been a few weeks since I moved into the house. It was about 1am and I was having vivid dreams of my now X-wife. I got up, walked to the bathroom and was about to take things in hand (you know what I mean) when I heard girls laughter from my back yard. I opened the sliding glass door and saw Xiu my daughter's best friend and Emily swimming in my pool. Xiu is a Chinese immigrant and like my daughter she is 18. Xiu is a small and petite girl. When you first see her you would think she was in high-school rather than a freshman in college. Xiu has a golden skin tone with long black hair. Emily is a mutual friend of Xiu and my daughter KC. I somehow got lost in looking at the two girls together wrapped in each others arms. Xiu: “Mr. Brown?” It was like coming out of some type of fog but finally I managed: “Hi Xiu.” Xiu relaxed a little but Emily was still petrified. Xiu has been to my old house a few times to visit my daughter KC. I'm a nudist and I sometimes forget to put clothes on. Xiu: “I didn't know someone lived here, but I am happy that it's you.” “Yea a few weeks now.” Xiu moved to get out of the pool but Emily squealed. Xiu kissed her on the cheek, gave her a reassuring smile and pried herself out of Emily's embrace. As Xiu came towards the ladder Emily moved to bury herself into the edge of the pool. Xiu rose up from the water and that's when I realized that she was nude. I heard an audible gasp and then realized it was me. Xiu was beautiful. I took a good long look at her youthful charms. From her pretty face and beautiful black hair. I let my eyes travel down to her tiny breasts. The sight of tiny cone shaped breasts, centered with tiny dark brown nipples made my breath catch in my throat. Small, high and perfect, they jut out from her small rib cage like two miniature balls topped with lovely dark brown nipples. And then my eyes traveled down to her flat and taut stomach, and her cute belly button; to her slender hips and to her most personal and intimate place. Her Venus mound was small and shaved into hairless smoothness. Somehow I managed to pull myself out of the trance. “Aren't you supposed to be away at school?” Xiu: “I still live at home and go to MLK Jr College. It was so hot today. Emily and I decided to go swimming” “At 1AM?” Xiu: “We've been swimming here for a long time. This house has not had a renter in ages.” I looked at her and she had this coy little smile on her cute face. I could see she was no longer looking at my face. I looked downward to see my erect phallus pointing straight at her dancing up and down with the beating of my heart. Xiu: “Please come closer so I can see you better.” With great trepidation I walked closer and before I knew it Xiu had a hand on my cock and I felt her breath on my testicles. She pulled, I came. Long ropes of jism splattered the deck. With the last spurts I couldn't stand and sat. My head was in a fog again until I noticed Xiu was pressing her body against mine. I felt her tiny firm breasts pressing against the side of my arm. Her tiny nipples were like fingernails poking into my biceps. I felt her small hips press against my wrist. I felt the warmth of her tiny pubic mound pressing and grinding on my leg. Her tiny body was on mine and she was kissing my cheek. She whispered: “Oh Mr Brown that was wonderful” as she nibbled my ear. As the fog was lifting from me she scampered in-front of me. Then she slid down and began to rub her vaginal slit on my fully erect phallus. How I got erect so fast I could not tell you but the feel of her smooth vulva sliding around my sensitive shaft. The tight pressure of her love box wrapping around the head of my cock. My phallic had taken over my brain. Xiu was rubbing her tiny titties on my chest, she gave a grunt and with a slight downward push of her hips my cock went inside her. Xiu: “OH YES” She pulled my head down and kissed me full on the lips and pressed my cock further into her vise like pussy. She jammed her tongue into my mouth and deepened the kiss. There comes a time in a man's life when things just happen. Can you blame me? A cute, young girl is passionately kissing me, she's riding my cock and rubbing herself all over me. I gave in and ground my cock as deep as I could into her. I kissed her back and started toying with those lovely tiny little titties. An orgasm rocked her body. Her little pussy put a strangle hold on my cock and I almost lost it but I held on. As the waves of her orgasm subsided I started to piston my cock in and out of her to deepen her orgasm. Soon she was as limp as a rag-doll in my arms. I lay her down, got on top of her and kissed her with my cock sill inside her tiny pussy. Slowly she opened her eyes and smiled. Xiu: “Oh that was wonderful.” I lightly kissed her lips and then trailed kisses down to her tiny titties. She took a sharp breath as I sucked a dart like nipple into my mouth. With no effort I sucked her entire golden globe into my mouth. I wrapped my tongue around her taunt little nipple. I sucked and pulled at the breast enjoying her texture and taste. With one last flick of my tongue I moved to the other breast and did the same. By this time Xiu was breathing hard and moaning sweetly. This time as I drew her breast into my mouth I plunged my cock into her pussy up to its base. Xiu came unglued with several hard orgasms. This time I couldn't hold back. As orgasmic waves flowed over her I shot loads of spunk deep into her. As our orgasms subsided I rolled Xiu on top of me and caught a gimps of Emily still in the pool. Her eyes were wide open and as big as saucers, her jaw hung open and it looked like she was in shock. I gave her a halfhearted smile and hugged Xiu close to me. I don't think my cock ever came out of her pussy as we lay there. We slept. Emily: “Xiu, Xiu it's time for school, we have to go.” Me: “What?” Emily: “Mr. Brown we have an early class.” Me: “Ah, understand. Xiu, Xiu, wake up sweetheart.” I gave her butt a nice hard squeeze and shook her shoulder. With a pop my cock came out of her. Her eyes opened slowly. Xiu: “Where am I? Oh I remember. Good morning.” Me: “Xiu we have no time, come on sweetheart you need to go.” Xiu: “Oh, OH NO! We have to go!” Emily was dressed already and Xiu's clothes were folded neatly beside us. Frantically Xiu was trying to wake up and get dressed. I helped her as best I could. Before they left I said: “You both can come swim anytime.” Both girls nodded and then rushed out the side gate. I lay there for a few minutes clearing my head before finally getting up to take a shower. The first thing I noticed was that my knees were bleeding from the rough concrete that surrounds the pool.
[F/M] She Let Me Cum on Her Panties
Note: Another in an ongoing series documenting my (sometimes) interesting sex life.
I arrived at the bar early, uncharacteristic for me on first dates. Its always best to keep the girl waiting, give the impression that you have something more important to do. However, for reasons of work, boredom, and my consistent desire to make rules, and then bend and eventually break them – I showed up early and started with whiskey.
She and I had messaged back and forth a few times about standard topics, and agreed to meet. I picked her mostly because she had a bit more edge to her in photographs than other girls. If you're looking for what I'm looking for, small details in the picture – tattoos, booze – are a dead giveaway that she won't be the type of girl occupying a spot at my family's thanksgiving table. We messaged briefly about work – she was a recent grad working at a design firm. A few terse messages later I suggested drinks at a bar in Hell's Kitchen, about halfway between my office and my apartment.
I'd just ordered my second whiskey when she tapped me on the shoulder.
Ex-girlfriend as a schoolgirl [M/F]
This is a recap of an encounter with an ex from several years ago, but is still one of the hottest encounters I have ever had.
My hands were gripping the steering wheel with final relief in anticipation of what was soon to come. It had been a long day, and relief was finally in sight. The only thing was that time was my worst enemy right now, and I had to get to the airport fast so that one of my fantasies could be fulfilled.
That One Time [MF/MM, strippers, mast, nogaysex]
This is the first erotic story I've ever written. Any comments, positive or negative, would be appreciated.
The six of us pulled up to the club around 10 on Saturday night in our minivan taxi, paid the driver $30 and hopped out. Outside of the club were a couple of guys smoking cigarettes and laughing. You could hear the low thump of music through the entrance and smell years of smoke build-up. This wasn't any of our first times to a strip club but it was our first time being to the Moonshine, a club known for "full nude full friction" $20 lap dances. Sure, it was Ryan's bachelor party, but we were all there for our own entertainment just as much. We are all in our mid twenties, average build, just out of college type guys working your typical entry level office and IT jobs. We all had girlfriends (or fiances!) and were just getting used to getting real paycheques every month. We all pretty much decided that this weekend we'd be putting that disposable income to use with fine scotch and lap dances.
Double dip on the weekend (m/f, m/f)
Chrissy had been sending flirty texts since our last date. She clearly enjoyed the makeout session in my car and wanted to go further. She wanted me to come down to her high rise to use the pool and enjoy the views that weekend. So on Saturday, I packed a swimsuit and took the el downtown to avoid the traffic. We went up to the sun deck to eat a quick picnic, before jumping in the pool. We didn't wait 30 minutes, living dangerously.
Chrissy was in a striped bikini. She has an athletic build with a bit of bubble butt. Her shoulders and arms have some muscles on them from her daily exercising. In the pool, she purposefully rubbed her ass against my crotch several times. Or maybe I was pulling her into myself. Either way, she knew she was getting me hard. She even confirmed it by grabbing at my cock underwater. I could only take so much before suggesting we head back down to her apartment.
Affairs of a Lifetime – Martinique
Lis (short for Lisolette) tightly squeezed my right hand with her left, her eyes wide open as her hips bucked wildly, screaming "don't stop, please don't stop!" Pulling her hips to him tightly, he kept fucking her through her first orgasm in over six months, ready to take her over the top again.
Lis had been divorced for three months. A former client of mine, we had become rather close friends over the past couple of years. She had called me just three days ago when she found out that friends of hers had to give up a short trip they had planned to Martinique and offered her two seats on the plane and use of a small cottage on the island. Lis really wanted to get away for a couple of days, her divorce being finalized, and truthfully, I also needed a short break. The next thing I know, I'm looking out the window of a Gulfstream IV and the island of Martinique, beautifully surrounded by the blue/green water.
Vacation Experience [M/F]
Well this isn't nearly as exciting as some of the stories I read here but I can promise that this one is 100% true.
My family always goes on vacation upstate to one of the great lakes. This is usually during mid-summer, about a week long, and has always been a chance to catch-up with family; mostly our out-of-state-cousins. We don't get to see them often, and for this reason, we usually only spend time with them and generally ignore any non-family.
Well a few summers ago this was not the case. Schedules didn't match and they couldn't come up at the same time as us. There is not much to do up there and to pass time I started to make friends with some of the other vacationers.
Unfortunately at the time of this story I am 22. I say "unfortunately" because I there is literally nobody else there in their early 20's, so there were not a lot of potential friends to be made.
(M)(F) she saw my post and sucked my cock.
So today while at work I received a message from Kari, the young lady from my previous story. It was a picture of her tight shaved hole with a caption "saw your story on Reddit and now I'm wet." I returned the favor with previously taken dick pic and offered to help satisfy her.
We agreed to meet during my lunch break at her apartment nearby. I practically ran up the two floors to her place and she opened the door half topless wearing only jeans. I expected there to be some making out but she grabbed my belt pulled me inside and went straight to her knees. She undid my pants as I threw my shirt and tie to the side and my erect dick popped out onto her cheek.