u/whatever_trev0r

Bi discreet with casual flirtations who wanted to experiment and explore before i got too old and had regrets.

Eventually found a site with trans escorts in my city who was close to office.

She described herself as a top only, Thai, 5 ft 9 and well hung. She was very good looking. I left work early after exchanging texts, excited and nervous. Have a shower and waited in bed.

I spent a good 20 minutes getting a relaxing massage as I could feel her warmth resting on my back. I flipped around and was obviously showing my excitement. She massaged my full body which took stress away and then flipped her body around in 69 position and started pumping her girthy monster in n out my mouth while i challenged myself not to
Let her down.

She would often hold it down in my throat to my delight , taking ownership of what was rightfully hers. Instructing me, to lick her balls which she loved to no end in addition to asking me lick the head and shaft and then ramming it in my throat again and again.

She was jerking me off at same time but my main focus was servicing her. Pulls out just at last second and cums all over my already soaked face, lips, cheeks. It was degrading and wonderful.

She sits back and lies down and i ask for permission to jerk off. She tells me she can wait but not to clean up my mess.

She dripping on my face and with her steady hand eventually cum all over myself after right at climax she sticks her tongue and tastes herself on edge of my lips and says dirtiest things ever.

Continue to see her since :)

I was in my late 20s at time , we had been getting roasted at beach during a European summer. It was the end of the day. For record i am Discreet bi with casual experiences but nothing more serious. Preferring women for most part.

Walking past a fruit stand after fruit stand trailing my friends and this old man definitely early 70s looked at me and made this comment in native tongue which i understood which was pretty much " I would love a piece of you" while biting his lower lip as i walked by.

Initially i doubted there was a group of women behind me but there wasn't. Get back to my hotel room and i cant get it out of mind. I went out that night came home at an ungodly hour and it crossed my mind again, within minutes i was jerking off to the thought of going behind the fruit stand and letting him have his way . Didn't realise i had that kind of kink.

My next day , the second to last day at this destination, curiosity got the best of me , decided to go past again but this time i stopped to buy something from him. Leaving beach early. What had come over me?

He caught onto me quickly " you're back i see, when do you leave?" , paralysed by assertiveness i answered " tomorrow " . He asked where i was staying obviously knew i was a tourist, pointed him to my ground floor apartment and advised him i was staying alone, friends still at beach till sunset had their own room.

He immediately told me he would meet me there and will follow me so noone catches onto us " how considerate i thought " . Open the gate of courtyard and leave door in my room slightly ajar.

Getting a good at him, he was stocky but looked after himself and strong all round , thick forearms , grey moustache matched with chest hair sticking out of his singlet.this wasn't his first time doing this.

Comes in and immediately drops his shorts , no discussion or anything, sensing weakness for older men on my part. I begin to jerk off his girthy looking cock while both of us looking at mirror.

After a good 10 of the filthiest dirty talk i have ever heard , calling me a secret whore who makes advances to old men ,making me very erect in my own beach shorts he lets out loud moan and cums all over the tiled floor. He grabs my head and asks me to get on my knees lick his cock clean and then some of it off the floor and off my hand which i do. Submitting was my thing.

I was expecting something in return but in true fashion he said he was done and needed to get back to his stand. That was it. Never saw him again.

I was in my late 20s at time , we had been getting roasted at beach during a European summer. It was the end of the day. For record i am Discreet bi with casual experiences but nothing more serious. Preferring women for most part.

Walking past a fruit stand after fruit stand trailing my friends and this old man definitely early 70s looked at me and made this comment in native tongue which i understood which was pretty much " I would love a piece of you" while biting his lower lip as i walked by.

Initially i doubted there was a group of women behind me but there wasn't. Get back to my hotel room and i cant get it out of mind. I went out that night came home at an ungodly hour and it crossed my mind again, within minutes i was jerking off to the thought of going behind the fruit stand and letting him have his way . Didn't realise i had that kind of kink.

My next day , the second to last day at this destination, curiosity got the best of me , decided to go past again but this time i stopped to buy something from him. Leaving beach early. What had come over me?

He caught onto me quickly " you're back i see, when do you leave?" , paralysed by assertiveness i answered " tomorrow " . He asked where i was staying obviously knew i was a tourist, pointed him to my ground floor apartment and advised him i was staying alone, friends still at beach till sunset had their own room.

He immediately told me he would meet me there and will follow me so noone catches onto us " how considerate i thought " . Open the gate of courtyard and leave door in my room slightly ajar.

Getting a good at him, he was stocky but looked after himself and strong all round , thick forearms , grey moustache matched with chest hair sticking out of his singlet.this wasn't his first time doing this.

Comes in and immediately drops his shorts , no discussion or anything, sensing weakness for older men on my part. I begin to jerk off his girthy looking cock while both of us looking at mirror.

After a good 10 of the filthiest dirty talk i have ever heard , calling me a secret whore who makes advances to old men ,making me very erect in my own beach shorts he lets out loud moan and cums all over the tiled floor. He grabs my head and asks me to get on my knees lick his cock clean and then some of it off the floor and off my hand which i do. Submitting was my thing.

I was expecting something in return but in true fashion he said he was done and needed to get back to his stand. That was it. Never saw him again.

It was in 2006 during my winter break to see relatives in Europe.
I spent time seeing the sites, seeing grandparents and cousins/uncles/aunts who happened to all live within walking distance of each other which was convenient .
When you meet family for first time you either connect real well and go over often to hangout and others you put them on repeat list.
My cousin Georgia , was very much on my repeat list during day especially as many were working during day. we just clicked.
Best way to describe her , dirty blonde long hair , about 5 ft 11, 41 at time, glasses, lean, who didn't mind a smoke on occasion and sultry in many ways.
She was daughter of my eldest uncle, one of 9 siblings i was son of youngest.
They lived in an apartment like many others and i liked to visit, have coffee and make fun of each other. She would pass her time cleaning house, hanging with neighbours, looking after her two teenagers and shopping. Nothing spectacular.
Often I would go for breakfast
There was nothing to it initially , cramped kitchen making food wearing a long night shirt with her back to us that showed her skinny legs, upper part of her thighs and a couple times reaching for things revealing her silk underwear.
I found it a little confronting but everyone was comfortable and her husband joked that we had a guest once but she quipped " he is one of us" which was correct . Never got the sense they were on the same page but I didn't pay too much attention. He drove a truck and did silly hours. Something my cousin pointed out when he would often not come home until late.
One morning i went over expecting to find everyone there but everyone had left early , she offered to make me breakfast since she slept in and i said sure.
Once again in her night shirt she worked away around kitchen and i will admit with noones watching i did pay more attention to her body and took more than a glimpse.
She was quick to point out that she didn't look like other cousins and was in much better shape despite her odd cigarette, seeking my approval to her question which while uncomfortable i had no choice but to agree, in response she did this wiggle of her butt in laughter with back to me. Impure thoughts started to flood my brain.

We went shopping immediately after that and she was very what's the word "clingy". Hooked my arm while walking, putting her arm around my shoulder leaning while window shopping. Have to admit she smelled great.

Around coffee she would quip never to get married and to enjoy single life. She just enjoyed the attention of barista flirting with her, (one of many ) and i liked being around her and played to it. Simple. She was fun.

Later that week it had been number of days since out last catch up, got off the train and decided to pop in unannounced.

She was frantic cleaning up for upcoming event, stuff everywhere , looking stressed. She was freaking out as she was briefly seated in kitchen taking a break told her i would help her and mocked a playful karate chop massage on her shoulders to relax. It was anything i would even deem anything but my attempt of humour

" i could use more of that "

So i did it again , mockingly of course, lasted about 10 seconds before she said to quickly rub her shoulders as she was stressed. I did so for a good couple of minutes where she got quiet and let out a loud sigh at end. She got up to continue her chores her perky nipples beaming from her heavy metal t shirt (another thing we had in common) from as she stood up rolled her neck around her shoulders it was impossible to ignore . I couldn't help but stare as she continued her chores.

A week later having coffee at theirs , My cousins husband commented in her presence how good a masseuse i was and i got extremely paranoid and worried but he when he saw my face , he laughed it off as did she say " he was better than you" but she was a little flushed by conversation. Well "i am not doing that again " i thought. I made an excuse to skip dinner and didn't go back for close to a fortnight.

We had a broader Sunday lunch at my uncle's and all were invited including my Georgia . Out of everyone she looked kind of overdressed, she came over and joked they thought i went missing. She was saying all this sitting on a hightened kitchen stool , her legs slightly apart wearing this skirt , stockings going up to a point which i was pretending not to see from my position on couch. Between her painted toenails, hair done to one side, faint hint of upper thigh and underwear on occasion and biting her chain looking at me it was hard to ignore. I rubbed one out that night to her and couldn't care less.

A week later, i went there as agreed expecting my other cousin to be there for lunch and it was a little tense and she wasn't talkative due to some inheritance issue with her husband gone wrong, which she frequently referred to him in not positive terms as she felt he botched this situation and would've possibly led to buying a bigger place. She felt "stuck" in her words

she straddled the broad and comfortable arm rest of leather couch in her low key house dress as she lamented the issue , stressing again.

As I consoled her , slightly tapping her shoulder as s matter of empathy she asked for a massage to relieve her stress.

I started my massage and did my best not to stare down her loose fitting dress which revealed something more than i expected.
After a minute or two she got up to get us more wine and i could see imprint of a wet spot on the leather. It changed the dynamic in my mind , blood rushing to my many heads.

I started up again as requested
as she reaches over grabs my left hand to say thanks and taps it , holds it longer , i end up lower where i end grazing her upper chest, it decended further down , i get a good handful and she doesn't let go.

End up seated right behind her also straddling the couch arm holding onto her breast with a firm grip , kissing her neck , letting out a broken English " yes yes" for what seemed like an eternity , she is literally rubbing her hands on her thighs constantly. lift her dress up, grabs my right hand and guides it in the warmest spot you can imagine, i get even closer behind her, and throw her leg over mine opening up even more and lean her further back, she responded to my assertiveness in a remarkable way, asking me to enter her i begin to penetrate her to oblivion making her cum soon after. Georgia blurted out "again"
This time i hold back her arms gently and do it again albeit slowly allowing her to recover and catch her breath and do this for an extended period, going from fast to slow , playing with her clit , even giving her a taste of herself. Couch is soaked and she slides up and down and eventually cums and shakes in this gorgeous way which even after all this time is etched in my memory. Held her for a while which she requested while cooling down. Got up, gave me a long hug and agreed to leave it there.. but made it a point to say "for now"

While I went back another couple of times before I returned home someone was always around , it was a little weird pretending it was normal but topic was never brought up ever again .

I was travelling for work and for life of me even when i woke up and on the flight i couldn't stop fantasising about sucking cock, i had casual flings before but this day it pre occupied to point i couldn't concentrate at work.

Downloaded Tinder on taxi back to hotel and on/off during the evening waited to see if anyone was around.

Eventually i got a hit in hotel, no real description but was mid 20s and away from his own woman. Described what had happened throughout the day and he said he would leave his door slightly ajar using a piece of clothing and waited for me

After a couple of minutes of pacing the room i got in elevator, room was dark , pushed the door open and this chiseled jock was sitting up in his bed stroking his very girthy 9 inch meat.

Took off my work shoes and crawled over still in my business clothes and proceeded to let out my insatiable thirst on this throbbing member for what in my mind felt like an eternity. He couldn't stop moaning directing me to lube his head, lick his balls while I surprised him with my gag reflex while he got brave and forced his head down to my delight multiple times calling me a good slut.

He eventually wanted to release, he stood up quickly and asked me to lie down while he stood over me and let out stream after stream all over my face , to degree he apologised for volume and handed me a towel.

While i thanked him I asked him to sit down and watch me masturbate while face covered eventually blasting my own stomach in process.

He came over semi hard, opportunistic while head hanging over side and throat fucked me for a few minutes before even he got too tired.

Eventually got up cleaned up and marched back to my room with his juices smeared all over me. So turned on I jerked off in shower again.

I was travelling for work and for life of me even when i woke up and on the flight i couldn't stop fantasising about sucking cock, i had casual flings before but this day it pre occupied to point i couldn't concentrate at work.

Downloaded Tinder on taxi back to hotel and on/off during the evening waited to see if anyone was around.

Eventually i got a hit in hotel, no real description but was mid 20s and away from his own woman. Described what had happened throughout the day and he said he would leave his door slightly ajar using a piece of clothing and waited for me

After a couple of minutes of pacing the room i got in elevator, room was dark , pushed the door open and this chiseled jock was sitting up in his bed stroking his very girthy 9 inch meat.

Took off my work shoes and crawled over still in my business clothes and proceeded to let out my insatiable thirst on this throbbing member for what in my mind felt like an eternity. He couldn't stop moaning directing me to lube his head, lick his balls while I surprised him with my gag reflex while he got brave and forced his head down to my delight multiple times calling me a good slut.

He eventually wanted to release, he stood up quickly and asked me to lie down while he stood over me and let out stream after stream all over my face , to degree he apologised for volume and handed me a towel.

While i thanked him I asked him to sit down and watch me masturbate while face covered eventually blasting my own stomach in process.

He came over semi hard, opportunistic while head hanging over side and throat fucked me for a few minutes before even he got too tired.

Eventually got up cleaned up and marched back to my room with his juices smeared all over me. So turned on I jerked off in shower again.

I was travelling for work and for life of me even when i woke up and on the flight i couldn't stop fantasising about sucking cock, i had casual flings before but this day it pre occupied to point i couldn't concentrate at work.

Downloaded Tinder on taxi back to hotel and on/off during the evening waited to see if anyone was around.

Eventually i got a hit in hotel, no real description but was mid 20s and away from his own woman. Described what had happened throughout the day and he said he would leave his door slightly ajar using a piece of clothing and waited for me

After a couple of minutes of pacing the room i got in elevator, room was dark , pushed the door open and this chiseled jock was sitting up in his bed stroking his very girthy 9 inch meat.

Took off my work shoes and crawled over still in my business clothes and proceeded to let out my insatiable thirst on this throbbing member for what in my mind felt like an eternity. He couldn't stop moaning directing me to lube his head, lick his balls while I surprised him with my gag reflex while he got brave and forced his head down to my delight multiple times calling me a good slut.

He eventually wanted to release, he stood up quickly and asked me to lie down while he stood over me and let out stream after stream all over my face , to degree he apologised for volume and handed me a towel.

While i thanked him I asked him to sit down and watch me masturbate while face covered eventually blasting my own stomach in process.

He came over semi hard, opportunistic while head hanging over side and throat fucked me for a few minutes before even he got too tired.

Eventually got up cleaned up and marched back to my room with his juices smeared all over me. So turned on I jerked off in shower again.

I was travelling for work and for life of me even when i woke up and on the flight i couldn't stop fantasising about sucking cock, i had casual flings before but this day it pre occupied to point i couldn't concentrate at work.

Downloaded Tinder on taxi back to hotel and on/off during the evening waited to see if anyone was around.

Eventually i got a hit in hotel, no real description but was mid 20s and away from his own woman. Described what had happened throughout the day and he said he would leave his door slightly ajar using a piece of clothing and waited for me

After a couple of minutes of pacing the room i got in elevator, room was dark , pushed the door open and this chiseled jock was sitting up in his bed stroking his very girthy 9 inch meat.

Took off my work shoes and crawled over still in my business clothes and proceeded to let out my insatiable thirst on this throbbing member for what in my mind felt like an eternity. He couldn't stop moaning directing me to lube his head, lick his balls while I surprised him with my gag reflex while he got brave and forced his head down to my delight multiple times calling me a good slut.

He eventually wanted to release, he stood up quickly and asked me to lie down while he stood over me and let out stream after stream all over my face , to degree he apologised for volume and handed me a towel.

While i thanked him I asked him to sit down and watch me masturbate while face covered eventually blasting my own stomach in process.

He came over semi hard, opportunistic while head hanging over side and throat fucked me for a few minutes before even he got too tired.

Eventually got up cleaned up and marched back to my room with his juices smeared all over me. So turned on I jerked off in shower again.

Discreet bi older professional man looking for someone (femboy plus) for someone that can please me during the day .Cant host. Open to anything

my friends girlfriend got tired of his endless partying, wanted him to stop because she wasnt getting enough attention that one night at club he asked me to walk her back to car because he was too high.
Her car was parked in a back corner of the lot and she spent the whole time complimenting me , holding my arm.
she was in heels and didn't want to fall all while telling me she was moving on from him if nothing changed (which eventually happened).
Get to car she pulls me closer suddenly , lets out " i feel lonely", kisses and she pulls my zipper down, starts stroking me , she then lifts her skirt waist high, grabs my head and i proceed to eat her out against hood of car, finally she cums , pulls me in closer , lifts her underwear back up asks strokes me point , staring into my eyes until i cum right in her underwear.
Tells me she wants to remember me tonight only so she pulls her skirt down still wet , sits in her car (leather seats thankfully) and leaves.

my friends girlfriend got tired of his endless partying, wanted him to stop because she wasnt getting enough attention that one night at club he asked me to walk her back to car because he was too high.
Her car was parked in a back corner of the lot and she spent the whole time complimenting me , holding my arm.
she was in heels and didn't want to fall all while telling me she was moving on from him if nothing changed (which eventually happened).
Get to car she pulls me closer suddenly , lets out " i feel lonely", kisses and she pulls my zipper down, starts stroking me , she then lifts her skirt waist high, grabs my head and i proceed to eat her out against hood of car, finally she cums , pulls me in closer , lifts her underwear back up asks strokes me point , staring into my eyes until i cum right in her underwear.
Tells me she wants to remember me tonight only so she pulls her skirt down still wet , sits in her car (leather seats thankfully) and leaves.

I was never close to this person until a period where we both happened to go clubbing together because noone was into electronica. After some pretty long nights of partying we both quietly realised we were comfortable with each other in many ways. Loved his women but it many questioned his softer demeanour to mean something else and bi curious and discreet at all costs in my self was attracted to it quietly.

We started hanging out at his house after a big night in his room watching porn and talking about our sexual conquests until one day moved to jerking off together side by side in his bed. Level of comfort with each other is something I never had before.

Our edging sessions would last a while and he was very complimentary about my cock and cum where i started doing same and more often than he would. The dam had broken.

I was the first one to help him cum , non hesitation on gripping his girthy cock and holding on until my forearm was exhausted and my hand full of his juices.

Soon after that as went out it became less about women and more about us , one night we were in car in middle of winter on a quiet road and started jerking in car before we went home empty handed. As he started and i admit i was a little high i asked him to move his seat back and took him all in , the first minute or two was figuring out what he liked and how i can improve but i figured as he was caressing my hair and moving my head up and down and as far down as i could go (and wanted to) i was good at it

After 10 or so minutes of it taking time to lick it all slowly, spitting on his shaft he held me firm and came non stop in my mouth and down my throat, letting out loudest moan i ever heard. Came up for air mouth full of his juices and asked if we could kiss , it was wonderful.

He quickly returned favour and it was obvious he was more experienced often coming up to get his juices out of mouth, until I couldn't handle it anymore and came like no other.

We eventually for reasons I can't get into parted ways long term but had that fond memory together

I was never close to my cousin until a period where we both happened to go clubbing together because noone was into electronica. After some pretty long nights of partying we both quietly realised we were comfortable with each other in many ways. Loved his women but it many questioned his softer demeanour to mean something else and bi curious and discreet at all costs in my self was attracted to it quietly.

We started hanging out at his house after a big night in his room watching porn and talking about our sexual conquests until one day moved to jerking off together side by side in his bed. Level of comfort with each other is something I never had before.

Our edging sessions would last a while and he was very complimentary about my cock and cum where i started doing same and more often than he would. The dam had broken.

I was the first one to help him cum , non hesitation on gripping his girthy cock and holding on until my forearm was exhausted and my hand full of his juices.

Soon after that as went out it became less about women and more about us , one night we were in car in middle of winter on a quiet road and started jerking in car before we went home empty handed. As he started and i admit i was a little high i asked him to move his seat back and took him all in , the first minute or two was figuring out what he liked and how i can improve but i figured as he was caressing my hair and moving my head up and down and as far down as i could go (and wanted to) i was good at it

After 10 or so minutes of it taking time to lick it all slowly, spitting on his shaft he held me firm and came non stop in my mouth and down my throat, letting out loudest moan i ever heard. Came up for air mouth full of his juices and asked if we could kiss , it was wonderful.

He quickly returned favour and it was obvious he was more experienced often coming up to get his juices out of mouth, until I couldn't handle it anymore and came like no other.

We eventually for reasons I can't get into parted ways long term but had that fond memory together

Me 25 at time Always got along well with Mary who we were family friends since my parents arrived to country , she was 45 , married at time 5 ft 6 , round everything just the way i prefer my women. I had a crush on her from teen days

I will admit that i had a great dating life and she knew i was a player and when visiting her place would often drink too much and in private get extremely handsy , rub my chest while asking me who my girlfriends were while wearing these loose hanging shirts showing her oversized breasts

Often would wonder in the kitchen as she was doing the dishes while everyone sat in the yard or living room post dinner complaining about her life/work and she would ask me rub her shoulders to get rid of stress

Would make it a point to ask what details she was interested in hearing and sometimes i would flat out lie and pretty much describe a younger version of her which would make her go red in face from embarrassment but would lead to her biting her lower lip in excitement , biting her necklace as I repeatedly tell her about our relationship and how she was one of many as she couldn't "keep up with me"

She would often call home pretending to speak to my parents knowing full well they weren't home which after a while became a secretive thing that would result in me just edging forever to her sexy voice at times just cumming right there on floor. Even after all these years she texts me all sorts of emojis on special events like my birthday and makes me wish to do more

Me 25 at time Always got along well with Mary who we were family friends since my parents arrived to country , she was 45 , married at time 5 ft 6 , round everything just the way i prefer my women. I had a crush on her from teen days

I will admit that i had a great dating life and she knew i was a player and when visiting her place would often drink too much and in private get extremely handsy , rub my chest while asking me who my girlfriends were while wearing these loose hanging shirts showing her oversized breasts

Often would wonder in the kitchen as she was doing the dishes while everyone sat in the yard or living room post dinner complaining about her life/work and she would ask me rub her shoulders to get rid of stress

Would make it a point to ask what details she was interested in hearing and sometimes i would flat out lie and pretty much describe a younger version of her which would make her go red in face from embarrassment but would lead to her biting her lower lip in excitement , biting her necklace as I repeatedly tell her about our relationship and how she was one of many as she couldn't "keep up with me"

She would often call home pretending to speak to my parents knowing full well they weren't home which after a while became a secretive thing that would result in me just edging forever to her sexy voice at times just cumming right there on floor. Even after all these years she texts me all sorts of emojis on special events like my birthday and makes me wish to do more