u/ClassicCreep66

I was 21 at the time.

While driving my fuck buddy ‘Megan’ (F18) and her ‘bestie’ ‘Ashley’ (F18) home from a party, Ashley was in the back seat and couldn’t stop talking to Megan about how she hated being single, needed to find a new man, all her fuck buddies were unavailable and how her newest dildo and vibrator would be getting extra work to do tonight because she was extra horny.

Ashley stared at me in the rear view mirror while I drove, almost salivating. Ashley was overly suggestive every time I had seen her, and Megan would tell her the juicy stories of us fucking. Girl talk. I knew she was hinting at something.

Megan was preoccupied trying to find a song on the radio and completely missed the cue. I tapped Megan on the leg and said ‘babe we’re free the rest of tonight aren’t we?’

Ashley smirked and twirled her hair around her finger. Megan finally paid attention to me instead of the radio, but had already missed the open invitation. I repeated, ‘we’re free tonight right?’ But Megan shouted ‘No we’re not free, we have plans!’

Megan’s plans were to fuck me in the car after Ashley had gotten dropped off. Those were my original plans too, but plans can change! Ashley sighed as we turned to her block, visibly upset. Megan, again, missed the cue and told Ashley ‘don’t worry we’re gonna find you a new man soon!’

Ashley slowly walked from my car into her place, as Megan started to kiss my cheek and pointed to the secluded road past the next stop sign. Directing me to park where the street lights wouldn’t shine into the car.

Once my cock was through my zipper and Megan was riding me in the back seat, I gently dropped the bomb on Megan and told her we missed an opportunity- if she had been paying attention. Megan reluctantly said she wasn’t into girls anyways, and wouldn’t have wanted to fool around with her friend. My fantasy ruined! But since she knew every guys dream is a MFF threesome, she didn’t want to disappoint me and promised me she’d start training for anal and I could fuck her ass next week.

The day comes for finally ducking Megan’s ass, and she accidentally lubed up my cock and her ass with warming-sensation massage oil/lube. Needless to say by the time her ass got comfortable with my cock in it, the ‘warming’ turned to BURNING and we had to stop as my cock was on fire and her asshole was burning too.

Double the let down!

I (M29) basically a 5’10 185 pound advanced dad bod, no visible abs but flat stomach, wide shoulders and big arms, had been crushing on Cassandra (F25) 5’1, 95 pounds-ish for a few months at the gym, but we had only exchanged glances and never actually met. We were always on the same schedule though, typically m-f between 5-7 or weekends around noon at the gym at the same time.

I was too shy to introduce myself any sooner, and also I wanted to keep our gym a creep-free area because you never know what anyone’s situation is, or make unwanted advances.

Anyway, one day I saw her struggling with her last set on a lift and stepped in before she hit failure. Even encouraging her to get a few more forced reps in, with me ensuring her safety.

Cassandra took off her headphones, as did I. I finally introduced myself and asked for her number, fully expecting to hear she had a boyfriend or that she doesn’t fuck where she lifts to avoid drama.

To my surprise, after exchanging numbers Cassandra said, ‘instead of just calling me some-day, why don’t you just ask me out right now’

I was somewhat taken back but stepped up to the plate. ‘How about an Italian ice type treat after a hard lift?’

Cassandra responded, ‘I’m gonna finish my lift now, but leave the cardio for later. Pick me up at 8, I’ll text you my address.’

I was in!

I quickly finished my workout and ran home to clean out my passenger seat and get freshened up.

Picked Cassandra up promptly at 8pm, and off to get an icy treat. We hit it off, the chemistry was insane.

We got back in the car and immediately started going at it, her hands fishing my growing cock out of my pants, mine lifting her form fitting maxi dress up past her knees into basically a mini skirt. Her Italian, tanned, toned legs were a mile along even though she was only barely over 5 feet tall.

We were parked down the block under a streetlight for some moonlighting. My cock fully exposed in her hands, I kissed her neck and ran my tongue down her collar bones and exposed her breast with my mouth. Taking her tiny pencil eraser nipple into my mouth, she moaned and begged me to take her home.

We arrived back at her place, I parked the car as she unlocked the door to her second story apartment and held it open for me as the landlords dog began to bark from me running past the first story windows.

Her dress was off before the door closed behind her.

Her shapely ass cheeks engulfing the tiny black strappy thong, I could only see the waist band as the rest sunk between. The maxi dress flew off over her as she had me follow her slowly up the steps. The steps were steep, my face was already buried as I grabbed her waist.

For a small girl she took my cock down her throat without gagging, her nose pressed against my belly button. Her tongue flicking towards my balls. She treated her body like a temple, every meal perfectly portioned, and it showed. She tiny labia lips had a delicious taste I couldn’t get enough of, my tongue prying her lips apart and sucking her juices out.

We cycled fucking and resting for a few hours into the morning, but we both had work in the morning.

I rolled over at least twice during the night and she engulfed me into her body, making me cum in her mouth every time because she wasn’t on birth control, and demanded to be natural without a condom. I couldn’t resist as it’s my favorite place to release, and she could tell by the way I quivered with each rope shot.

One more romp in the morning and off I went to work in the same clothes as I had for our date.

At about noon she texted me, thanking for making sure she hit her cardio for the day and that she wanted to see me again.

But said she got a ‘noise complaint’ from her landlord this morning and said we’d have to go to my place if we wanted to go all-out again.

I (M29) basically a 5’10 185 pound advanced dad bod, no visible abs but flat stomach, wide shoulders and big arms, had been crushing on Cassandra (F25) 5’1, 95 pounds-ish for a few months at the gym, but we had only exchanged glances and never actually met. We were always on the same schedule though, typically m-f between 5-7 or weekends around noon at the gym at the same time.

I was too shy to introduce myself any sooner, and also I wanted to keep our gym a creep-free area because you never know what anyone’s situation is, or make unwanted advances.

Anyway, one day I saw her struggling with her last set on a lift and stepped in before she hit failure. Even encouraging her to get a few more forced reps in, with me ensuring her safety.

Cassandra took off her headphones, as did I. I finally introduced myself and asked for her number, fully expecting to hear she had a boyfriend or that she doesn’t fuck where she lifts to avoid drama.

To my surprise, after exchanging numbers Cassandra said, ‘instead of just calling me some-day, why don’t you just ask me out right now’

I was somewhat taken back but stepped up to the plate. ‘How about an Italian ice type treat after a hard lift?’

Cassandra responded, ‘I’m gonna finish my lift now, but leave the cardio for later. Pick me up at 8, I’ll text you my address.’

I was in!

I quickly finished my workout and ran home to clean out my passenger seat and get freshened up.

Picked Cassandra up promptly at 8pm, and off to get an icy treat. We hit it off, the chemistry was insane.

We got back in the car and immediately started going at it, her hands fishing my growing cock out of my pants, mine lifting her form fitting maxi dress up past her knees into basically a mini skirt. Her Italian, tanned, toned legs were a mile along even though she was only barely over 5 feet tall.

We were parked down the block under a streetlight for some moonlighting. My cock fully exposed in her hands, I kissed her neck and ran my tongue down her collar bones and exposed her breast with my mouth. Taking her tiny pencil eraser nipple into my mouth, she moaned and begged me to take her home.

We arrived back at her place, I parked the car as she unlocked the door to her second story apartment and held it open for me as the landlords dog began to bark from me running past the first story windows.

Her dress was off before the door closed behind her.

Her shapely ass cheeks engulfing the tiny black strappy thong, I could only see the waist band as the rest sunk between. The maxi dress flew off over her as she had me follow her slowly up the steps. The steps were steep, my face was already buried as I grabbed her waist.

For a small girl she took my cock down her throat without gagging, her nose pressed against my belly button. Her tongue flicking towards my balls. She treated her body like a temple, every meal perfectly portioned, and it showed. She tiny labia lips had a delicious taste I couldn’t get enough of, my tongue prying her lips apart and sucking her juices out.

We cycled fucking and resting for a few hours into the morning, but we both had work in the morning.

I rolled over at least twice during the night and she engulfed me into her body, making me cum in her mouth every time because she wasn’t on birth control, and demanded to be natural without a condom. I couldn’t resist as it’s my favorite place to release, and she could tell by the way I quivered with each rope shot.

One more romp in the morning and off I went to work in the same clothes as I had for our date.

At about noon she texted me, thanking for making sure she hit her cardio for the day and that she wanted to see me again.

But said she got a ‘noise complaint’ from her landlord this morning and said we’d have to go to my place if we wanted to go all-out again.

I (M29) basically a 5’10 185 pound advanced dad bod, no visible abs but flat stomach, wide shoulders and big arms, had been crushing on Cassandra (F25) 5’1, 95 pounds-ish for a few months at the gym, but we had only exchanged glances and never actually met. We were always on the same schedule though, typically m-f between 5-7 or weekends around noon at the gym at the same time.

I was too shy to introduce myself any sooner, and also I wanted to keep our gym a creep-free area because you never know what anyone’s situation is, or make unwanted advances.

Anyway, one day I saw her struggling with her last set on a lift and stepped in before she hit failure. Even encouraging her to get a few more forced reps in, with me ensuring her safety.

Cassandra took off her headphones, as did I. I finally introduced myself and asked for her number, fully expecting to hear she had a boyfriend or that she doesn’t fuck where she lifts to avoid drama.

To my surprise, after exchanging numbers Cassandra said, ‘instead of just calling me some-day, why don’t you just ask me out right now’

I was somewhat taken back but stepped up to the plate. ‘How about an Italian ice type treat after a hard lift?’

Cassandra responded, ‘I’m gonna finish my lift now, but leave the cardio for later. Pick me up at 8, I’ll text you my address.’

I was in!

I quickly finished my workout and ran home to clean out my passenger seat and get freshened up.

Picked Cassandra up promptly at 8pm, and off to get an icy treat. We hit it off, the chemistry was insane.

We got back in the car and immediately started going at it, her hands fishing my growing cock out of my pants, mine lifting her form fitting maxi dress up past her knees into basically a mini skirt. Her Italian, tanned, toned legs were a mile along even though she was only barely over 5 feet tall.

We were parked down the block under a streetlight for some moonlighting. My cock fully exposed in her hands, I kissed her neck and ran my tongue down her collar bones and exposed her breast with my mouth. Taking her tiny pencil eraser nipple into my mouth, she moaned and begged me to take her home.

We arrived back at her place, I parked the car as she unlocked the door to her second story apartment and held it open for me as the landlords dog began to bark from me running past the first story windows.

Her dress was off before the door closed behind her.

Her shapely ass cheeks engulfing the tiny black strappy thong, I could only see the waist band as the rest sunk between. The maxi dress flew off over her as she had me follow her slowly up the steps. The steps were steep, my face was already buried as I grabbed her waist.

For a small girl she took my cock down her throat without gagging, her nose pressed against my belly button. Her tongue flicking towards my balls. She treated her body like a temple, every meal perfectly portioned, and it showed. She tiny labia lips had a delicious taste I couldn’t get enough of, my tongue prying her lips apart and sucking her juices out.

We cycled fucking and resting for a few hours into the morning, but we both had work in the morning.

I rolled over at least twice during the night and she engulfed me into her body, making me cum in her mouth every time because she wasn’t on birth control, and demanded to be natural without a condom. I couldn’t resist as it’s my favorite place to release, and she could tell by the way I quivered with each rope shot.

One more romp in the morning and off I went to work in the same clothes as I had for our date.

At about noon she texted me, thanking for making sure she hit her cardio for the day and that she wanted to see me again.

But said she got a ‘noise complaint’ from her landlord this morning and said we’d have to go to my place if we wanted to go all-out again.

TLDR: tinder one night stand, her genetically shallow vagina led to her love of anal and oral. Confirmed during our only date where my fingers were in her ass, she refused to fuck, only mutual masturbation but swallowed my cum anyways.

We matched and met on a dating app, and hit it off through texts, calls and video chats.

‘Cameron’ (F21) had already send photos of her tight body in lingerie, teasing me before meeting me only a few days later.

She had briefly mentioned she was born with what she called a genetically shallow vagina and gave a warning that typical penetrative sex was virtually off the table because it was so painful and she may never have children.

I appreciated her bringing up the discussion because some people wanting children is a deal breaker and that’s fine.

Her caveat was that she discovered this when she first started dating and it led to her love of oral and anal sex to ‘make up for what she could give’ to her partners.

Of course I had to meet her. Stunning, tall, lean but busty.

Light blue eyes that stared into your soul and pitch black pin straight hair.

We met and instantly connected almost as if we had met before or were lovers in a past life. The chemistry was undeniable.

She felt the same. We spent the next several hours discussing where we could have crossed paths before, maybe younger while on vacation or each having distant relatives that knew of each other.

We could have swore we had met and missed the connection back then.

We never found out if there was a prior meeting, but I did find out her outer perfect body did have the inner problem.

After drinks and eating, we ended up back at my place. But she told me, ‘not so fast, I don’t fuck on the first date.’

We did basically everything else though,she winced uncomfortably upon just one finger dipping into her sopping wet pussy. No more than a second knuckle before I felt her cervix.

She sucked on my finger then guided my hands towards her rear, virtually shoving two fingers immediately into her asshole. She moaned and told me to only play with her ass and to focus on her clit and not enter her vagina again. I graciously complied.

She began to stroke me, spitting into her hand and squeezing the helmet of my cock tighter with each pass. She bent down and licked the first drop of precum from my head.

Within minutes I was ready to blow and she quivered from me licking her clit and her pussy continually dripping onto my fingers inside her ass. There were 3 now and she asked me to thrust them back and forth.

She came and then huddled into my arms. Legs twitching before telling me it was my turn.

I could barely hold myself back from shoving my cock into her absolutely tiny hole. Her ass was gaping now, but she pulled me by the base of my cock back to her mouth, becoming more demanding that she WONT fuck on the first date and that includes anal.

I couldn’t believe she wanted mutual masturbation, my fingers in her ass, my cock inching closer to her mouth.

‘You’re not putting that inside me, in ANY hole on the first date’

Refusing for my cock to pass her lips as she only licked me from the base, along the shaft to the throbbing top of my cock.

I said ‘i don’t even know what you want me to do anymore’ there was no blood in my brain anymore, but she responded, ‘just cum in my mouth, don’t miss and mess up my makeup.’

My cock millimeters from penetrating her lips, the only hole which she would let my cock near, began to spurt violently. I emptied my load onto her tongue, no drop went unclaimed as each rope shot into her waiting mouth.

She gurgled my cum , spit it in her hand and sucked it back into her mouth. Playing with it over and over again.

I fell to my side of the bed, watching, wondering what type of woman would let me do such things to her, but make certain STRICT physical limitations.

I dropped her off in the morning and our paths faded in different directions, but I’ll never forget the one night with the anal loving, cum swallowing, genetic anomaly, almost 10 years my younger.

I (was M21) and was living my best single life about a decade ago.

When Jenn was home from college, we would mess around but never actually fucked. We finally did towards the end of summer. She wore a short skirt and stockings when she came over, a simple blouse and sweater as she was headed out to a family event after stopping by. We fucked for about 45 min, every position you could think of, finally shooting my load into a condom. I ate out Jenn for another 15 minutes before she left to make sure she came too.

Jenn left around 9 o’clock in the evening and within minutes my friend called, saying he would come pick me up and we would head to our favorite local bar.

When TJ picked me up, we met with a few of our mutual friends, his gf and his gfs friends and the drinks started flowing.

Just before closing time, my friends gf asked me if I wanted to have an orgy. I asked my TJ if she was being serious and he said ‘you can fuck her, because then I get to duck one of her friends!’
I was in! TJ was in!
TJs gf was slim but had a toned body with perky tits, how could I say no?

I went back across the bar and asked TJs gf, so who else would be in this orgy? She said whoever you want!
I picked her friend, the short, cute, cleavage showing, Chloe.
Eventually we left the bar and went back to my place.
TJ and his gf started going at it, making out, and she dropped to her knees and took his whole cock into her mouth.
Chloe paused while making out with me, our hands all over each other and said ‘let’s kick this up a notch I can’t be out-done’, then ripped off her top, grabbed me by the belt and yanked my cock out of my jeans.

I spun her around and slid directly into her soaking wet hole, making sure we got to fucking before our friends, and carried her across the living room to another couch, all while balls deep and thrusting. Chloe was petite and loved to be tossed around.

We fucked until the sun came up, I came three times but continued to eat her until my erection would come back.
I collapsed after the 3rd load and Chloe jumped up, realizing she needed to go home because it was the morning.

I woke up TJ and his gf, asleep on the original couch, who angrily stormed out of the room with Chloe.
TJ took me aside and told me I ruined the night, because he came over to ‘switch’ and I was too busy pounding into Chloe and never noticed!

In hindsight I was upset too because I missed out on fucking my friends girl. But i also knew with fucking Jenn and then Chloe, banging two girls in one night isn’t always easy to achieve.