29 [M4M] Any Straight Alpha Males Down To Chat/Roleplay?

I have lots of roles I’d like to try:

You: Str8, Cocky, Arrogant, Tough Alpha Male. 6’5 tall, muscular (I have pics of guys you can play as), packing a beautiful 8×6.5 dick. You know you’re sexy and can get any chick you want. You’re all about your pleasure and love to fuck rough.

Me: Gay Beta. Shy, maybe a little odd. 5’5, skinny, black hair. Brown eyes.

I like my roleplay partners to play hard to get-be annoyed by my character at first or weirded out. I also like things to play by ear.

1A. Alpha Male at The Bar
You’re out at the bar checking out chicks. You see one you like, convince her to give you head out in the alley/in your car. I follow to watch the show.
1B. You’re a business guy out with a female client. Maybe you’re married, maybe not. I watch you guys flirting all night and offer a proposition…
2. My Straight Roommate
You come home late from a night out with the boys and brought a “friend” with. Hearing the noises from your room, I get a little curious
3. My Boss’s Bachelor Party
I’m brand new to the company and to be nice, you invite me to your bachelor party. A night of drinks and strippers-this oughta be good…

He wanted to be with an asian girl. I wanted to try BBC. My boyfriend wanted to watch. It was a match made in heaven [MF]

So girls talk. To my closest friends, I’ve admitted and discussed my open relationship with my boyfriend. We were a small group and there were very little secrets between us. I’ve had a few adventures (you can see a few stories I’ve posted here) and they’ve always been curious about what it’s like and how it’s been. I don’t tell them all the naughty details but just more the emotional aspect and how it felt when I was able to break out of my previous shell.
I knew my friends since High School and I definitely was not the same confident woman I try to be (or at least show in my writing). I was awkward and shy but my friends were not so they always tried to help me realize my potential? Truly, I was not a very cool person to hang out with but I did have great friends. It wasn’t until university where I really had my glow up and started finding my style, embracing being cute or sexy when needed and accepting my awkwardness. So for them to hear about all the fun I’d been having was a complete culture shock and one where they had so many questions about.
It inevitably became a conversation about what is “left” on our lists in terms of what we wanted to try. Now all of us were in long term relationships and I was the only one who was in an open relationship so a lot of the kinks were not so unique. Anal, BDSM, roleplay. I felt like I was the only one who had the opportunity to explore more so I quickly threw out one that my boyfriend and I were always curious about. Big black cock.
We all laughed and joked about how “if you go black, you can never go back”. It wasn’t an experience they have had either and with the wine flowing, we just joked around and I thought that was the end of it. It wasn’t until the end of the night, my friend Rachel kind of pulled me aside and talked to me in the kitchen as we began cleaning up.
“You know, I’ve heard that Christian might be… what you might be looking for” She told me. I gave her a confused look and she quickly made a phallic gesture with her hands. Christian was a mutual friend of ours from High School who also went to the same university as me. We were never close but we were in the same circles so I knew him enough. I can’t say I was ever attracted to him even though he was a good looking guy but I was immediately intrigued. The fantasy was mostly driven by my boyfriend but I’ve quickly learned that when my boyfriend loves something, it became something that I loved too. I talked to Rachel and secretly implied that if Christian were to find out I was in an open relationship, that will be ok with me. I don’t like to advertise this news to people that I don’t trust given the backlash it gets sometimes but he was trustworthy and I wanted to see what he would do with this information.
The night ended and I headed up to tell Harry, my boyfriend, all about it including about Christian. We watched some BBC porn (it soon became one of our many favorites), we played it up in our own personal time and that was that. At least until a couple weeks later when I got a DM on IG from Christian.
“Hey it’s a shame we go to the same school and haven’t hung out in a while. How have you been?”
Now it’s not out of the blue for him to message. We like each other’s photos, we are in the same group chats but in this case, it was clear what was happening. We messaged back and forth and eventually migrated to text before I questioned him about his intentions. He was quick to admit that Rachel had told him something that he wasn’t sure he was supposed to hear.
“It’s true. Harry and I are in an open relationship.” I confirmed his suspicions and the conversation immediately took a turn. From the very casual how are things, reunions are hard to come by, people we know are getting married shock to the now dirty talk, everything was on the table. I admit the texts are gone now so I’m just basing this on memory but we talked about my previous experiences and how he was single but enjoying that part of life. At one point, we talked about porn and how we’ve wanted to explore more fantasies which inevitably led to us talking about BBC.
Harry was watching the conversation and we both were turned on just seeing the ramp up to what we felt was inevitable. He insisted I send him a picture of myself just to move the conversation along since in his mind, we were dancing around the idea of us fucking each other’s brains out. So I sent a very suggestive picture of me entering the shower. It took many efforts before Harry and I were happy with the shot. I entered the shower and immediately was responded back with what was probably one of my favorite dick pics. I remember being in the shower, water running down my back as we began texting back and forth.
“Fuck me that cock is gorgeous”. It immediately got steamy and I sent more photos while he sent videos of him stroking himself. At one point, he tried to facetime me but I couldn’t just keep wasting hot water like that.
We would continue to sext for weeks, for some reason never wanting to meet up. I think part of me had that reluctance of actually indulging into this fantasy, worrying that maybe if I do go black, I can’t go back. Harry was happily enjoying the texting and seeing all the sexting we were doing. We knew that there was a moment where we’d both be in the same place and that was at our mutual friend’s wedding. There was never any discussion over it, never any planning. We both knew we were going and we both knew that all of this was foreplay towards that evening.
I remember not meeting up with any other men during those few weeks. Again, I don’t really remember my mindset around that time beyond just feeling immensely satisfied with my boyfriend and with sexting Christian. Christian and I would send each other porn and gifs to watch and he would continue to mention how he’s never been with an asian women. Yellow fever never really did it for me but for some reason, the fantasy and taboo of it just made it incredibly hot in the moment.
By the time the wedding weekend was here, Harry told me he didn’t want to go to the wedding but instead, just wanted to wait in the hotel room for when I would finally bring Christian back to our room. He wanted me to text him throughout the night and just be ready to watch all of it unfold in front of him. I was confused and honestly a little upset. I had RSVP’d with him and it felt rude to not go but I could tell that this was a fantasy he really wanted so I obliged.
I went to the wedding in a somewhat figure hugging olive green dress with my hair curled and my makeup done. I remember entering the wedding ceremony and nervously looking around to find Christian but not seeing him. Rachel even gave me concerned looks wondering if I was worried somebody was after me. I told her no no, everything is ok. The ceremony ended and it was absolutely beautiful but Christian was nowhere to be seen.
We went to reception and I mingled with a lot of my old classmates and the classic talk about how Grad school was, how my boyfriend was, was I enjoying where I lived and did I miss my hometown. I remember stuffing my face with some hors d’oeuvres before a deep voice behind me said “You look gorgeous Trish” only for me to turn around and be almost speechless. Christian stood in front of me and I don’t know if it was just his outfit or the weeks of foreplay but I was just mindblown attracted to him at that point.
We flirted and talked throughout the night and even though we sat at different tables for dinner, we found ourselves back to each other afterwards. We danced, laughed, and drank a lot but all relatively PG around our friends. But every quiet moment alone, he’d almost always find a way to tell me something dirty. “Call me daddy tonight” he’d say as he’d gently brush his hand over my ass. A few times, when we thought we had some privacy, I could tell he wanted to kiss me but I told him that I wanted all of what we do to be in the hotel room for Harry to see. He understood the fantasy and was ready to play it up.
The night slowly ended and we opted to take an uber together back to the hotel. Our mutual friend joined us (just to minimize suspicion) so the sexual tension in the uber was palpatable. His leg pressed against mine, it felt like we were trying to break the fabric between us. We reached the hotel and awkwardly our friend was also on the same floor as us so we went to our separate rooms before I texted him my room number.
Harry sat quietly in the corner of the room watching as I opened the door only to be met with force as Christian pulled me close by my waist and kissed me as the door closed behind him. It was pure lust as we’d be gasping for air before our lips met again, me doing my best to rip off his clothes and undo his belt. I knew what I was after. When it finally was just his underwear left, I ripped it off and immediately was met with the largest cock I’d ever been with. I remember putting both my hands on it and saying “Holy fuck, what am I supposed to do with this”. I kissed the shaft and licked it, doing my best to get a reaction out of Christian and Harry. Harry sat, cock in hand as he slowly stroked matching my rhythm before I did my best to wrap my lips around this big black cock.
My jaw was not enjoying it but my body knew that I needed to conquer this. I took many breaks, stroking it with my hands, kissing it, teasing his full balls but I knew that it wasn’t my mouth that was going to win. I looked up and begged for him to fuck me. “Daddy, please just fuck me” I said as he positioned himself over me. I was so wet at that point as he fingered me, continuing to make me beg for his cock. I remembered closing my eyes, my head tilted back as I was in heaven but still wasn’t given what I was after. I told him again and again “Please give me your cock”, only for him to tease the entrance of my pussy with his cock until finally, he pushed in.
It was a wild feeling, him thrusting slowly into me. I felt my body almost adjust for him as I took deep breaths watching it impale me. I had my hands on his chest, doing my best to pace him as my body slowly warmed up to it, me almost wincing every time he pushed deeper. But he had his own pace and he started to push more and more as I told him to please slow down. My legs pulled him in, doing my best to control the rhythm but he fucked me his own way. Harry watched and later on described me as “fighting for my life”. Apparently my eyes were wide open doing my best to focus but in my mind, all I remember was being completely lost in the moment and feeling incredible as I came onto his cock.
I pulled his face into mine and told him I wanted to be on top as we made out, him slowly rolling us over. I began to slowly push myself down and up, quickly learning that he was my favorite cock to ride. It was incredible, being able to just ride him with complete control given his size and every movement was so pleasurable. His hands ventured to my nipples as he pulled them, almost making me scream in pleasure. But he wanted control again and he held my waist and started fucking me from underneath as I rested my hands on his shoulders. I could tell he was getting close to cumming and I was just a toy for him to use. He pulled out just before he came, took off the condom and started stroking his cock right in front of my face as my body was shaking from the fucking I received. He came all over me as I sat there in shock of what I had just experienced.
I pulled his cock and slowly began licking him and blowing him again. I was his slut that night and I wanted him to know. I cleaned his cock up with my mouth before we went to clean ourselves up in the shower. Harry came in after us, completely in a mess as we talked about how that was one of his favorite experiences he’s ever had. The alcohol was at that point too much and after our shower, we all collapsed on the bed, with Christian spooning me naked in bed.
We woke up early in the morning (I never sleep well when I had many drinks) cleaned up and laid in bed, me stroking his cock awake. We talked about last night, casually joking around while I stroked him and him telling me how gorgeous I looked holding his cock. He would later fuck me from behind against the hotel window, telling Harry that “everybody needs to see how much this slut loves my cock”.
Christian and I after that night spent a lot more time together. We realized that we had a lot of mutual interests and obviously enjoyed fucking each other like animals. There was so little judgment that we almost used each other to fulfill each other’s secret fantasies. We would do all kinds of roleplays, he’d tell me his favorite lingeries or outfits, I’d be wearing wigs and costumes, he’d tie me up and make me his sex toy. It was incredibly enjoyable and satisfying.
It did create some unhealthy jealousy between my boyfriend and him so our sexual relationship had to eventually stop but we remained good friends. I don’t miss the sex but I do look back at the memories and think about how good some of those moments were. I might talk about our last encounter and dive more into the jealousy in a future story. We are quite open about talking about these things and really want to promote healthy communication! Hope you all enjoyed the story and again feel free to let me know what you enjoyed!!!

The Princesses in the Tower – Chapter 5, Part 6 – Agatha [Maledom] [Male supremacy] [Humiliation] [BDSM] [Spanking] [Les][Dubcon] [Plot heavy]

**Agatha**

Harlots are new ladies. According to that motto, I proudly exposed my tits and made a way to my cunt. The new age was lenient towards me, but some gentlemanly demands rose. That is how it came that I alternate between being a teacher and a student. As soon as I explained to the group of inmates, completely pale with fear, how they could improve their results in Lovemaking, I put on a green evening dress in my room. It covered my legs, but the neckline didn’t leave much to the imagination. I left my underwear and chastity belt in the room. Nowadays, they assume a high-class lady makes concessions to men. I will not by trying to resist any ideas that Beck or Mayson would have when looking at me. Sophia could try something too.

The management slightly changed the hall of the principal’s office into something like a cut-out corner of a restaurant. My lovers and chit-chatter stood at the table with Mayson at the top.

Stiletto high heels heralded my arrival in the carpetless hallway. The principal and the sexologist welcomed me. I wished them good evening, kissing their hands according to the new ritual. The principal gave us his blessing, and we took our seats.

The MILF Saga. The Education of Will. Chapter 1 – The Seduction of a Young Man Behind the bar, Will

The MILF Saga. The Education of Will.
Chapter 1 – The Seduction of a Young Man

Behind the bar, Will was a pleasant figure. A nice young man of 22 with a quick wit, earnest attention and the gift of easy conversation. He smiled easily laughed pleasantly. He looked like an athlete with broader shoulders than most young men his age with strong, muscular arms that peeked from beneath his well fit polo shirt. His shoulders narrowed in a V down to a size 32 waist. As a former collegiate athlete, a pole vaulter, he came by it naturally.

Women liked him, college coeds and young working women found him desirable. They patronized the popular bar and restaurant where he worked, by the dozens. As a group they all dressed the same, similar styles of the day. Dating them or finding a sex partner came fairly easy almost too easy. To him it was like eating vanilla ice cream, each bite tasted delicious, but in the end it was still vanilla.

Strip Cards [M35/F35, M30/F28]

“How do I look?” Adriana asked her husband

“Fucking hot as always.” He replied.

Adriana was a 5’6” 35 year old brunette. She loved to lift weights and had the curves to show it with an ass that filled her tight fitting jeans nicely. Tonight she and her husband Bradley were meeting some friends for dinner.

Bradley was looking her up and down. The top of her perfectly round breasts spilled out of the top of her blue lacey tank top. All he could think about was having her perfectly pink erect nipples in his mouth.

“I would like to fuck you right now.” Bradley added.

Adriana’s pussy tingled at Bradley’s words. She absolutely loved fucking her husband. His 6’2” frame was in amazing shape. He kept his head shaved and had a nice trimmed beard. He had biceps to squeeze her, abs that showed through his shirts and a rock hard ass that filled in even his loosest fitting pants. Tonight though, they had dinner plans and they were running late.

“I would like that too, but we better get going.” She responded.

[MFM] A Mask for the Camera

I love living in Portland. There is nothing special about the neighbourhood that we live in, but downtown offers so much variety in such a small space that it’s an easy way to have a quick vacation and pretend that we have gone somewhere far away. We love to go down to a hotel in the Pearl district and then just go walking.

There is a seedy little sex shop right by Powell’s bookstore that my wife, Anne, loves to go in and browse. The very first time we went in the clerk was this very cute manic pixel girl type who flirted shamelessly with my wife and offered to help her try on a corset. My wife has always regretted turning her down. So, every time we are there we visit the same shop. Mostly due to fond memories, with a tiny little hope that the manic pixie girl will be there again. She never has been.

The last time we were there was a bit strange. Things were lifting from the worst of the pandemic and we were out again. But everything still felt very subdued. Everyone seemed to be on eggshells. The area wasn’t as lively as we remembered either. Dirtier, grittier. Everything felt like there was a pall of sadness hanging over it.

I [F] spent the night with my boyfriend, but all we did was behave like a bunch of bunnies. [24F]

I’ve already discussed how college is subtly brainwashing me into loosening up, making new friends, and exploring my sexuality despite coming from a traditional and conservative background. So a few months ago, I started a small friendship group with six men and six women.

I currently share a home with a successful, gorgeous, smart, and popular man who went to the same university as myself. Since I truly want to have sex, I quickly realized that he was only there for the sex. It wasn’t long before we were having as much sex as we could, usually skipping lectures or other classes in the process. Even though we didn’t always get the chance to get together and fuck as much as we wanted, it was still pleasurable. My family prevents me from being out till rather late at night.

I’m pretty sure [M]y friend is a sugar baby, and I did an embarrassing amount of detective work

I’ve known this friend for about a year, we’re in grad school together. I knew of her through some mutuals in undergrad but didn’t really know her that well. What I did know was she was fun, outgoing, too flirty for her own good, and a body count in the low thirties.

When we got into the same grad program, we started hanging out more and I got to know her better. She definitely lived up to her reputation, telling our friend group about all the hinge “husbands” she was juggling. I also learned she has very expensive taste. They were taking her to NHL games every week, to nice restaurants, nicer bars, the works. She definitely had a certain taste.

She was also working part time at a country club to earn some extra cash. Not that she needed it, she just liked having it to go shopping. She’d drop a casual $100 on candles, online shop during almost every class, and go out for lunch most days. She was definitely making enough off tips to support that, even if that meant no savings.

I finally did it! I secretly met a fan and WOW… what GREAT sex it was! I have a feeling I might do this a bit more often! [M29/F39] (cheat)

So while I (30’s) have sneaky cheats, up until this point I haven’t met any actual fans of mine – I just had random encounters with people while out by myself, a group of friends, or whenever it clicks and the timing is right.

While traveling with my partner and visiting friends in another city one weekend, I decided to see if one of my fans (late 20’s / early 30’s) wanted to meet since we’ve been having pretty consistent, and decent exchange of messages.

He had a partner too, and was located about 3-4 hours away from where we were visiting.

Needless to say, he made the drive (I don’t know what he told her) and we decided to meet one day. I told my partner I was going shopping to a few sales to see what was on offer, and borrowed one of my friend’s cars.

We met up over drinks in a pub with some food. Everything went great. He was charming, chatty, and not too forward or vulgar. Things just clicked.

So we got us a room and for like the next 2-3 hours we f*cked like lovers in heat to extremely slow passionate sex.

My Rebound was a Squirter [MF]

I was a few years out of college and into the corporate world. No more parties, no more available women at every corner, it was depressing. What made it even worse was being recently single, long distance almost never works out. I was determined to enjoy the single life however, and made use of all the newly available dating apps. I have a few stories from those another time.

I managed to meet this girl at a buddies party. She was younger than me by a few years, just out of college. Jessica was about 5’6” with straight blonde hair down to her shoulders and dark brown eyes. Her body was tight from years of competitive dance, with an ass every guy at the party stared at when she turned around. Her tits were smaller, about a handful, but incredibly perky. Especially when she bounced around the room flirting with different people. She was nice, but I could tell she was a little crazy. If I only knew.