Fulfilling a Fantasy (m/f)

Last time I told about how my apparently nymphomaniac girlfriend took my virginity. I'll get back to more stories with her eventually, but for now all that's important is that she broadened my sexual views and desires greatly.

This time, I'm going to cover two other firsts. The first time I cheated, with the first girl I ever lusted after. If you don't want all the back story, just skip to the paragraph starting with "I wrapped my arms around her…"

In my earlier years of high school, I was good friends with a girl named Beth. She was a dancer, which showed in her well toned muscles. Blonde, fair skinned, and an incredible body. She didn't have very much in the way of tits, but she made up for it with an ass that can only be described as bootylicious. She was the first person I knew personally that I masturbated to.

We would hang out a lot and often work on jigsaw puzzles (yeah, we were kinda nerds). Regardless, it was non-threatening enough of an activity that her parents were completely comfortable with me, and didn't bother checking in on us, or making me go home before they went to bed on the occasional evening where I'd join them for dinner.

Gonewild with my father-in-law

Day after my mom-in-law's funeral, my husband's dad comes to stay with us 2 weeks to heal, and for privacy we let him use our ensuite bedroom. Everyone tired that 1st nite, after tucking kids in bed I headed straight to bedroom, undressed, switched off light and snuggled close to hubby. Hubby surprisingly grabs me intimately and we made love, not lasting 3 minutes as we quickly came together. As we lay hugging he whispered: "I knew my son wasn't pleasuring you well, he's never cared much about women." I jumped out of bed as I realized I'd been fucking my dad-in-law, grabbed my clothes and ran to the guest bathroom to put them on before going to the guest bedroom where my husband was already sleeping. It was the longest and most embarrassing fortnight of my life.

How I fucked [M]y pregnant best [F]riend for the first time.

Back story in the comments.

I had a huge job interview coming up in Montreal. Both Zoe and myself love the city so she decided to come with me and make a little vacation out of trip. I booked a place for the week on airbnb, we bought train tickets, and off we went. We spent the first night there eating, dancing, and drinking. Well I drank. She had water and and bought me shots.

I must have been drunker than I thought because I don't remember getting back to the room, or going to bed. I remember waking up to look at the clock around 7am, and became immediately aware of several things. I was only wearing my underwear, I was spooning very closely with Zoe, she was only wearing a tshirt and underwear, and I had some serious morning wood. Pressed hard against her ass.

(M)y (F)irst time cheating

This all happened before I met Beth, but it was the start of everything I believe, after this event is when I started to see prostitutes and massage parlors.

My wife and I have been married for about a year or so, and it kept getting bad with her, arguing all the time, belittling, all the fun stuff. I got to a point where I had a hard time handling the stress from work and from her.

My ex started texting me asking to talk, her bf of 5 years finally broke up, and she needed to talk. I came over one night expecting just to help her through, but we never had a chance to fully finish what we had together.

When I got over there, it only took half an hour for me to lose it and just want her badly. She admitted she wanted the same but she was trying to hold back because I was married now.That night when I went home, she texted me saying she made a mistake, and shouldn't of held back. We set up a meet time the next day after she got off of work, to just talk again.

Dressingroom fuck … (m/f)

Me and my wife went out the other day listening to gone wild audio in the car. We like to get riled up in public, all the way to the store (target) I'm rubbing her off under her skirt while she is stroking my cock over my jeans. We get to the store and we have to make a decision. To go in and shop? or pleasure each other in the parking lot… so we compromise we head into the store. We can't keep our hands to our selves. She grabs some target panties and we head to the changing room. She teases me a while trying on some cheap slutty thongs and then she starts to suck me off. And God she is amazing! being in the dressing room she has to keep the sucking noises to a minimum but she doesn't let that stop me from cumming down her throat. She sucked the cum from my cock until i was drained. She did not want to stop. Of course why should she! She still hasn't gotten hers. I dive down to her pussy and start licking and kissing her lips. She wanted me to keep the panties on during this whole ordeal. She likes when I slowly work my way around her pussy till she starts dripping and her clit comes out play. as I start sucking on her clit I start to get hard again. She sees my cock and starts working with it, rubbing the shaft and going down to suck on my balls. She is getting me ready for a second orgasm. She is still wearing the cheap thong I think it was black but to be honest that was the last thing I was thing about. She climbs on to if me and starts to ride my cock. Pushing the thong to the side as I slide in her dripping pussy. Back and forth she moves grinding her clit on the base of my shaft as I thrust as deep into her as i ca. Again being quiet so no one knows were fucking in a changing room. I love when she gets close, her butt clenched and she starts to shudder as goosebumps over take her body. It is the biggest turn on when she has to hold the moan as she rocks in bliss. At that moment I reposition for my final act I come from behind and by this time it only takes 5 or six slow powerful pumps for me to release my hot load inside of her.

My first time: Jock[m] and skinny nerd [m]

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.

Is that a dick? Yeah.. That’s a dick… So guess I'(m) bi now. (mmfm)

Now I have always been for all things anal. Fingers in my ass during blow jobs etc.

As you may know from my previous story, I dove dick-first into the world of group sex with my fuck buddy Kristi and her friend Kurt. That happened a few more times until they both moved away to do their own things.

Enter Marc and Erika. Marc I met at a bar. He was about five years older than me at the time (I was 21). Marc was a 6'2 and super fit black guy. He had graduated from a college in the area where he played DII football and was now an accountant or something with money. We bonded over sports and shit and I was soon introduced to his wife Erika. A taller and muscular black woman, who played basketball at the same school Marc went to.

Lucky for me, they are swingers! So we messed around a couple of times. I'd bring another girl on occasion for a foursome but there was this one time…

Marc has a friend in town… a former teammate and we all go out drinking (him, Erika, Jason and myself). Jason's a good looking white dude, stereotypical bro with not much going on between the ears.

My Teacher’s a Nudist?! [MF, exh, voy]

A breeze wafted in from the ocean, ruffling the pages of The Demon-Haunted World. I slipped a bookmark in and set it onto the warm, eburnean sands around me. Waves lazily marched towards the shore, only to crash and dissipate once they reached their goal, their rhythmic susurrus a natural lullaby. The scent of the tropical sea surrounded me with a brisk, briny, clean perfume. In the clear, cerulean waters, two young women played a game of their own devising, the object of which, so far as I could tell, was to fail to hit the ball in such a way that you made the biggest splash and the most noise possible. I sighed.

I had to admit, I was surprised that their nudity no longer even registered as something noteworthy to me. After just a few days at the Kutná Hora Resort, I no longer felt any trepidation at being nude. No longer did I fear the other guests would point and laugh. I had even stopped worrying that I was going to walk outside naked, only to realize I had made a huge mistake and this wasn’t a nudist resort after all.

Prostitution and the art of catering for the nouveau riche.

Harold has relatively recently come into quite a lot of money. I don’t know how if it’s changed him as I didn’t know him in his previous financial state.

He’s also become a major user of prostitutes. It annoys our manager that he uses other agencies as well as hers. He does 2 or 3 bookings a week with us spending up to £15000 a month, she just sees the money she’s losing to her competitors.

‘Find out what he’s doing with the other agencies’ she tells us before each booking, she suspects it’s BDSM, and has stressed to us that we’re meant to offer light BDSM as part of our regular services. She’s made sure that all the girls do outcalls with him are taking the BDSM paraphernalia with them.

He likes to watch. While we use toys on ourselves or each other he’ll wank himself. He used to be shy about doing it, but he's pretty blase about it now. He also has a fondness for spanking and anal sex, unfortunately giving rather than receiving.

He’s recently become enamored with lesbian sex, but he insists on mixing and matching women himself rather than letting us pick who we want to work with.