Straight Virgin Loses A Bet And His Anal Virginity_(3) free porn video

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This tale takes place about 13 years ago when I was in school. At this age I was fairly awkward and unaware of how attractive I was. Years of a passion for rock climbing and puberty had recently changed my body from that of dorky awkward boy to that of a fairly attractive teen. Spending 3-4 days a week at the local indoor rock climbing gym along with normal PE activities and running and lifting had given me a very Lynn strong body. I had a toned 6-pack, VERY large and toned forearms for my size (135 lbs) along with a strong back and a decent tan that I got from doing yardwork shirtless for spending money. I was also fairly hairless, except my pubes which I had just started shaving because I preferred the feel of bare skin while masturbating my ignorantly large 8-inch cock. Which I did constantly.

Ever since I was young I always had an uncommonly high sex drive. So much so that I was caught masturbating in class more then once. This is one of those things that led to my misconception of how attractive I was. Getting caught playing with myself in class had turned me into a social outcast throughout most of my school experience, and in my head no one that’s that socially shunned could be a cool hot guy. Along with a misconception of my attractiveness, I was also misled about the size of my cock. This was because with the exception of the cocks I’d seen in porn magazines, the only cock I had seen before was the occasional glimpse at my brothers when we both had to pee at the same time. As a result, I had no idea what a normal size cock looked like, and since I didn’t have high self-esteem I assumed I must be on the smaller side of average. I was soon to learn that wasn’t so.

I haven’t finished this section of the story yet, honestly it’s a boring part of the story that only really sets up the continuity. Eventually I will and I’ll post the revised version. Until then though the next paragraph cuts to a party that I ended up at by accident with 8 people from my high school. Bibi, my ex-girlfriend who was openly gay. Lyn, the Czechoslovakian foreign exchange student that was rumored to be bisexual and have a “European attitude towards sex.” Missy, my friend from elementary school who Bibi dated for years before she dated me. This mixed with the fact that Missy had a thing for me made her have a lot of animosity for me. Kat, a very hippie friend of mine who smoked a LOT of weed and would get insatiably horny when she did. Sadly, she wasn’t attractive to me, but I did like how intelligent she was. Mathew, a quiet timid blonde boy from my school. I had recently learned that he was gay, in the closet, and apparently attracted to me. Ty, a fashionable tall black gay guy from my school. I didn’t know him well, but like Mathew apparently he was ALSO attracted to me. Ty, Micah’s current boy toy who I knew nothing about other than he was timid, curly haired, blonde, and skinny. And last but not least, Micah. The most openly gay teen from my high school. He had short brunette hair, a skinny fit body, and was VERY opinionated. He got off on bringing out the homophobia in straight people.
Cut to the party. Were all in Kat’s room, passing around 2 pipes of weed and fairly stoned.

After taking another toke of weed from the communal pipe, I noticed Ty, Mathew, Micah, Ash, Bibi, and Lyn were missing. I heard girls giggling in the closet and saw bodies moving under the bedsheets. That’s when my obliviously stoned brain put two and two together… this wasn’t a normal party, it was a bisexual orgy!! The giggling in the closet was my lesbian x-girlfriend, Bibi, making her moves on the Czech foreign exchange student, Lyn. And the movement under the covers was surely Ty and Mathew! I couldn’t believe what I was in the middle of!! This was the start of a teen bisexual orgy with 8 other people in the room! Then a crazy thought occurred to me, Bibi was my ex. From both her and her ex Missy I had heard that Micah was VERY attracted to me and Mathew and Ty were also. Ontop of that I knew that Missy and Kat were attracted to me, because they had both admitted as much when we were high months prior, and I had a suspicion that Lyn also thought I was attractive because she would flirt with me in English Lit class a lot. Where was this leading?

At that moment Micah and Ash walked back into the room smiling and blushing. Micah had an erection clearly visible through his tight jeans. He must have noticed it caught my eye, because he turned to me, grabbed his dick through his jeans, and said “Do you like this? Big isn’t it? I bet it’s the biggest you’ve ever seen.”

This wasn’t the first time Micah had fucked with me like this. He legit believed that there was no such thing as “straight people”, just people who haven’t come out of the closet yet. He also got off on flaunting his homosexuality in front of any straight male in our high school to get a rise out of them. When he got said rise he would call them things like “homophobic breeders!” He especially liked to toy with me, as he currently was, because he thought I was “clearly closeted” and had admitted to my ex that he “wanted to fuck me.” Not to mention I’m sure he fantasized about turning my straight cock. This made me detest him, even though part of me was VERY attracted to him. He was right to some extent, even though I thought he was an asshole, I was attracted to him! But I also was attracted to women slightly more and still am. So I wasn’t “gay” like he thought, I was bi. And even then some part of me knew that.

So when he flaunted his cock in front of me I got the great idea of challenging him to a size comparison. Whoever had a bigger cock had to do whatever the other one wanted. For me that was for him to leave me alone and stop hitting on me, for him that was probably to finally get the chance to turn me like I guessed he wanted to. He acted apprehensive, but agreed on the stipulation that we were “hard when we compared.”

I said “Obviously, but who will get me hard?” Knowing full well that Ash would be his fluffer.

Micah smiled at me and said “I can do that.”

I told him to “Fuck off.”

That’s when Missy, who had been watching this whole thing play out stepped in and said “I’ll do it, but you can’t tell anyone at school about this!”Being fairly attracted to Missy, I said “Ditto” and agreed.

As Ash pulled Micah’s pants down slowly I noticed he had a huge grin on his face that made me nervous. He wasn’t wearing underwear and the first thing I noticed was his upper pubic area. It was shaved uncommonly smooth, possibly even waxed knowing Micah. Next I saw his shaft, as his tight jeans slid down they revealed the shaft of his cock. The further down they slid the more shaft they exposed, it just kept going. That’s when I started to get a sinking feeling as inch after inch of Micah’s already half-hard shaft was exposed. Finally, after what seemed like ages, his head slipped out and I saw all of his enormous cock! I couldn’t believe what I was seeing, he must have been 7 inches long already and he wasn’t even hard! I knew I was fucked, possibly literally.

Ash grabbed Micah's shaft and started moving his hand up and down. Then he took Micah’s cock into his mouth and deepthroated it until it disappeared inside his esophagus before pulling it back out, glistening with saliva. He kept this up as Micah looked me over like a piece of meat he was eager to bite into. At that moment I started to feel myself get hard. The thought of that giant cock was making my mouth water, but why? I was caught like a deer in the headlights not even realizing how much I was staring at his now rock hard cock. IT MUST HAVE BEEN 9” LONG!!

My gaze was finally broken by Missy, who had pulled my pants and breifs down and had just slid her hand around my already hardening shaft. She spat on it before sliding her hand up and down. I was already harder than I’ve ever been at this point, but she still slid her mouth over my head and started working it slowly, getting me as hard as possible to gove me a fighting chance. To this day I don’t know if she did that to hide the fact that in front of everyone else in the room I was getting turned on by Micah getting a blowjob from Ash, to help me get a leg up by making sure I was as hard as possible, or simply because she had just wanted to suck my cock, but I suspect it was a bit of all three.

After Missy blew me for a while I looked up to notice that Micah had his cock out of Ash’s mouth, rigidly sticking nearly straight out with a slight curve, and was waiting for me. His cock seemed to twitch with anticipation. I tapped Missy on the head and she pulled my engorged 8” cock out of her mouth. It was at that moment that I realized that she and the 8 other people in the room were all watching to see how this played out. I thought “This is so crazy!” But I had taken this to far to stop.

I tried to hide what I was thinking and act confident, but my nervousness must have been obvious because Micah looked me right in the eye and asked “You like what you see? I hope you do, because I’m going to make you worship my cock all night!”

I pulled myself together and responded “We all know you like what YOU see. Don’t get too excited yet.” I thought that was clever, little did I know I was just digging the hole deeper.

The moment was up. It was time to compare despite the fact that the winner was obvious. Micah must have known I was too nervous to make the first move, so he walked up to me and before I could react he grabbed my cock and held it up against his, arranging them so his was on top of mine, foreshadowing what was to come. With our members pulled together, mine pulsing with nervousness, his with anticipation, he slid his down mine until his head touched my lower stomach. But there was a little over a solid inch of space between my head and his balls. The winner was clear, but regardless he said out loud for everyone to hear.

“You lost. Now take off your shirt and get on your knees! Your gonna start by sucking my cock”

Shaking with nervousness, I responded “But…. You…… in front of everyone?”

And he replied, “This could’ve been private, but you dug this hole for yourself. Now your my slave for the night and you’ll do as your told!”

I looked around and the 8 other people in the room were anxiously watching, a few of them had visible erections. I looked back at him and then at his massive cock, still hard as ever. At that moment I accepted my fate. He won fair and square. I was going to be Micah’s boy toy until sunrise.

I took off my shirt, now completely naked and exposed, and got down on my knees as I was told. I was shaking so hard; this wasn’t supposed to play out this way!! As I thought about what Micah might do to me he grabbed the back of my head and guided my mouth onto his massive cock.

My mouth stretched open as his head slid past my moist shaking lips. Then he kept pushing as his shaft slid down my throat until his head hit the back of my throat. I never told anyone this, but I have almost no gag reflex. This came in handy as he pushed harder and forced all of his 9 inches down my throat until his balls rested on my chin. I remember the scent of his balls was intoxicating. He then told me to look up at him and said “I knew you were a good little cock sucker!”

Then he pulled his cock out to the tip fast and pushed it back down my throat even faster. My face started turning red and he said “breathe through your nose! This isn’t stopping anytime soon!”

He was right, his repeated this for a good 10 minutes. Shoving his cock down my throat faster and faster. His balls slapping against my chin over and over as my throat became sore. He then pulled his cock out of my mouth, dripping with my saliva, and pulled me up to my feet.
As I stood up he turned me around and shoved me against the wall face first. Then he grabbed my legs and pulled them open before pushing down on my back until my face pressed against the wall. Then he got down on his knees behind me and took a big wiff of my ass before shoving his face into my ass crack.
I felt his hands grasp my asscheeks and spread them open, then something wet and warm started probing around my asshole!! IT WAS HIS TOUNGE!! I couldn’t believe it; this was all happening so fast. And the crazy part is………I was liking it. No, I was loving it. Just then I gasped as his tongue slipped inside my tight virgin asshole!! My cock twitched and hardened even MORE as he drove his tongue in and out of my ass!! I gasped with the intense pleasure.

Micah noticed and pulled his tongue out to say "your liking this aren't you you little slur?"

I responded "No, I'm straight Micah!"

To which he said "sure you are slut!! No straight guy sucks cock that well" before shoving his tongue back into my now slick asshole.

At this moment moaning from the bed caught my attention. I looked around and noticed Bibi had dawned a strapon and had Lyn bent over the bed, pounding her pussy while Lyn watched Ty drive his huge black cock into Mathews asshole while Mathew had his face buried in a pillow. Then on the floor I noticed Kat had her face buried in Missy’s vagina, making her shake with pleasure!! Everyone else had clearly followed our lead after I lost the bet. This was it, the orgy was happening and I was part of it. We were a writhing mass of bodies!!

Part 2 to come soon!!

-->

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Shabana Slut Loses Virginity

Hi you would have read a few stories of mine by now ,let me narrate a story of one of my horniest girl friends named Shabana.She is 5 ft 7inches tall with boobs of size 36 flat tummy and a 36 inches ass.She likes taking dick in her ass too and has over last few years turned into a real slut ,let me narrate her story: Hi I am Shabana ,28 years old ,married and my husband has 4inches dick which is never enough to satisfy my hunger for sex.I was virgin till I was 18 ,but used to keep masturbating...

1 year ago
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It was serendipity that I lost my anal virginity

Each person remembers their first time for the major events in their lives such as going to school, a date, kiss, and sexual intercourse. For the more adventurous, anal sex can be enjoyable for both the person receiving (bottom), and giving (top). On study has reported that 40% of married couples had experimented with anal sex. The report continued by saying few men has experienced the pain and pleasure of receiving anal intercourse. At the age of forty-three, I had my first bisexual meeting....

Bisexual
2 years ago
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Andrew Loses It

Andrew walked home from the party. No, he didn’t really walked, he stumbled and staggered, legs held as wide apart as he could, nursing an asshole that only a few hours earlier had been the virgin bud of a true stud, and was now gaping obscenely. Even as he walked he felt it throb and pulse… and he felt the warm liquid leaking down along his inner thighs – liquid that could only be Thomas’s cum. His mind kept going back to the party – a party to which he had been specially invited and to which,...

3 years ago
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Randis Vacation Part 3 of Randi

Randi's Vacation Randi woke up to his alarm and quickly silenced it. A quick glance to his left confirmed the Denise was already up. She almost always got up before him preferring some extra time between getting ready for work and needing to walk out the door. He preferred to have enough time to get ready, eat and go. He walked to the bathroom which was right in the master bedroom. The condo they bought was a bit extravagant but provided plenty of room and they could afford it on...

1 year ago
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Chanda Ki Gandi Chudai 8211 Part 2

Hum dono abhi bhi nange hi thay. Chalte chalte usne paad maari. Uski gaand mein abhi bhi haddi akti hui thi. Nadi kinare, jhadiyon ke bich usko bithaya. “Hug le saali madarchod. Kab se paad rahi jai bhosdiki.” Woh hugne lagi. Uski gaand se haddi nikal gayi. Uski garam moot ki dhaar mere pairo pe giri. “Saali maderjaat! Mere pairon pe mootegi. Saali raand muh khol,” main uske muh mein mootne laga. Lavda uske gale mein ghus kar mootne laga. Maine apni tange faila di aur wahi khade khade hugne...

2 years ago
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Losing my anal virginity

This is a true story of how I lost my anal virginity to a random stranger from Craigslist. Posted anonymously elsewhere.—————————————I cheated on an ex gf with some guy I found on Craigslist. I had always considered myself straight (despite the cross dressing and panty obsession), yet had been growing more curious as I got older.A few years ago (in my early 20s), I was flat sitting for friends while they were away, and I was on the Craigslist casual encounters section (more out of interest than...

1 year ago
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Michelle the Anal Virgin

Michelle the Anal VirginI've met michelle in a coffee shop in central Tel Aviv. She is a 160 cm, nice tan and perky ass and tits. She was in her early 20s. I drank coffee and she drank coke. Both set with our laptops working during the day. I don’t know how we started but we discussed our research. Apparently Michelle looked for an MA studies in social science and the chat evolved on life, work her workaholic boyfriend. From this and that we got along and one day, and in some others we used to...

1 year ago
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My first analloosing my virginity

So recently(yesterday) i had my first anal experience, as well as loosing my virginity with a man. Being as thats the only hole i have, there wasnt a choice. Anyways, both the guy and myself were both in to kink and so we got to the room and undressed. He was immediatley hard and i got to work with his shaft deep in my mouth. It was eight and a half inches and thick, however, i managed to deep throat the whole thing! He started with just calling me slut and things like that then he bagan...

1 year ago
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Fling with an Anal Virgin Free Sex Stories and Adult Erotica Stories

I met Sophia through an online dating app. We have been going out for some time now. The feelings are mutual and by the looks of it, we are going to be strong for a long time ahead. Sophia is rather tall with a very curvy body. Her boobs and ass are exceptional. Especially her ass is so shapely that it is hard to believe they are natural. She has a very innocent and beautiful face too. It has been a while we have started being intimate physically. Her body is a wonder and I cannot have enough....

Anal
1 year ago
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Chanda Ki Gandi Chudai 8211 Part 1

Mera naam Rudra hai. Ek number ka harami aur besharam. Mera dimaag mere lavde mein hai, jo saala har waqt chudai ke liye uchalte rehta hai. Kasarati badan jo ghanto tak lavde ka saath deta hai. Waise toh bachpan se hi kaafi chudai ki hai. Lekin yeh wali sabse achi wali, ya yeh kahu ki sab se gandi wali hai. Main tab 30 saal ka tha. Shaadi hui nahi thi. Ghar mein rehta hi nahi tha. Naukri hi aisi thi ke sheher-sheher gaon-gaon bhatakna padta tha. Peshe se ek civil engineer, jiski degree paiso se...

3 years ago
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Histoire de Sandrine

Histoire de Sandrine (1)Par Perverpeper le 15/05/08F/f F+/f F/f+ F+/f+ teen enema exhibition WaterSport bestriality BDSM feet hair slavery scatology college hightSchool job slow reluctant humiliation blckmail torture nc HeavySynopsis?: Sandrine est une jeune lyc?enne. Quelques jours apr?s avoir f?t? ses 18 ans, alors que le baccalaur?at n’est plus qu’? quelques semaines, elle est enlev?e par une femme richissime qui l’initie aux peines et aux joies de la soumission.Adressez-vous plut?t aux passions qu’aux vert...

4 years ago
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My Anal Virginity

We stood in the small shower facing each other, both of us soaked; our long hair plastered to our backs, and both of us completely naked. Our cocks were exposed but not hard, each hanging innocently between our legs, brushing up against the other in a casual way that gave no hint at the desire burning beneath the surface. We were two smooth, hairless twinks taking a shower together. We stood close, not even a foot away from each other, yet we were not kissing. Our heads were turned slightly to...

3 years ago
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Valentine Virgins Alessandra Val

This is about ALESSANDRA. Scroll down furthest for her. Well and my other Virgins I've digital, only a few of tem dozens, 2 or 3 or 4 of them dozens. All them before they met me. And till met me.'Meat my meet" I always say. Proud of my big (20cm) bent brown BANANA for them to suck.Not too fod of haing one inside her somewhere. She's very 'tight'. Mostly in her sphincter, which no-one is allowed to touch. Never Lez Kiss.Alessandra loves it most, at man. & sperm.the taste of dick But she's...

4 years ago
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Andrea Standing part 2 of Andreas Stand

Andrea Standing (part 2 of Andrea's Stand) A note at the beginning. One of the problems with writing a serial story is that the author feels a need to recap what happened in the prior portions. Please go back and read part 1, "Andrew Running". It will make this a better story. Briefly Andrew at 19, abused by his father, runs away to a distant relative, Aunt Clara. Andrew goes along with a joke played by Clara's lover Marnie, and ends up as Andrea working in Marnie's luxury used car...

4 years ago
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Dads Porno Magazines Chapter 3 James Loses His Virginity

When Karen left James's room, she took the magazine that she was looking at with her. She still could not believe what had transpired this afternoon. Part of her was telling her it was wrong, but another part of her was reminding her of how much fun it was, and it would be ok as long as James didn't cum in her or Carrie's pussy. She laid in bed, her asshole still feeling a little weird, but she couldn't believe how it had intensified her orgasm with her brother's finger in there. She was...

1 year ago
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Ann Loses The Bet But Enjoys Her Loss

Ann and Will were an older couple that enjoyed sex and exploring their fantasies. Since meeting on Lush several years ago, they had gone from cyber-lovers to physical lovers. As they became physically connected, they had found many ways to enjoy each other. They never failed to try something new in their relationship if one or the other wanted to try it. This had broadened their sexual appetites in many ways and found them always stretching the boundaries of what each other would do. Today was...

Spanking
2 years ago
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Losing my Anal Virginity to a guy from Grindr in his RV

For a little information about me, I was a 18 year old 6’2 athlete with a nice bubble butt that guys seem to love so much. At the time I was at a boarding school and would just go on Grindr and chat and trade pics with other guys. I would talk to a lot of guys in my area but the only problem was that I was in a such unpopulated area that there weren’t many guys very close to me and I was not able to travel since I didn’t have a car. There was this one guy who had such a nice big white cock...

1 year ago
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Our First Time 8211 Shy College Girl Loses Her Virginity

Hi everyone, this is my first story on ISS. It is about how I took the virginity of my best friend turned current girlfriend during my engineering days at MIT. The girl in the story is named Priya, she is a very shy girl from a reserved family. We met each other on the second day of college and became friends immediately. I myself coming from a reserved family understood she felt insecure and found it difficult to trust people initially. So after being patient for 2.5 years, I finally managed...

1 year ago
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I fucked a grandma that was my grandpas whore

There was a 70 year old grandma that moved in right next to my apartment, I was 18 at the time and my grandpa was 74. I lived with my grandpa at the time. The old grandma would come to talk to my grandpa each day, she would keep teasing him, she would flirt with him, she tried to seduce him. My grandpa ignored her at first but then he started flirting with her after a couple days. I once came out of my apartment only to see her sucking his dick outside on the porch while he was touching her...

3 years ago
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Teenage Anal Virgins

Joking aside, I remember being a horny young guy; experimenting, fooling around, feeling guilty, not sure if I was weird and hoping I wouldn't be caught. It would have been so much easier if I had someone to guide me and tell me that my feelings were completely normal. Luckily for Dan and Tim, they have me to point them in the right direction. As the guys were leaving my house after our first sexual lesson, I told them that instead of risking getting caught or in real trouble risking...

3 years ago
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Teenage Anal Virgins

Dan and Tim are eighteen and nineteen year old guys who are members of the Surf Life Saving Club that I'm a member of. Last week I caught Tim on his knees just about to suck off his teenage friend. It was a Friday afternoon and they expected to have the equipment sheds all to themselves, Tim was on his knees when I walked in on their naughty act. They were terrified that they were in trouble. Instead of being in trouble, the two young guys came back to my place and started their sexual...

2 years ago
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Bet of My Life Randis Day

Bet of My Life- Randi's Day I sat in the lab, my hands trembling. After years of painstaking research, with electrodes taped to my head attached to a bank of machines, I had imagined the reality-bending device. And....voila! There it was, a smooth device a little larger than a phone, appearing on the table in front of me out of nowhere. Professor Nichols and the others had snickered about the work behind my back. They'd tried to get my funding pulled numerous times. I was...

3 years ago
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Pregnant but Orally and Anally a Virgin

I am reposting this story, friends!PREGNANT BUT ORALLY AND ANALLY A VIRGIN!It was winter vacation(2011). College was out. I had gone to my parent's house to stay there for a while. Besides our house, lived a couple-a software engineer and his (hot and sexy; 25 year old) pregnant wife. It was a rainy evening. Mom and Dad had gone out of the town for a work. I was all alone watching TV throughout the day. My Mum called me and told to visit the house next to our's for getting back some money. I...

3 years ago
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Elizabeths story Chapter 7 Gary takes my virginity

Chapter 7 Elizabeth’s story – Gary takes my virginity Friday: As I had promised Gary last night (Thursday night), I took steps to get contraception for our planned big event; the capture of my virginity by my stepbrother. Although I still had serious reservations about doing this, I was committed to keeping my promise and giving myself to Gary as soon as it was ‘safe’. Midday on Friday I skipped my study hall, lunch and poli-sci class and went to the local planned parenthood clinic to get...

Taboo
1 year ago
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Britney loses her Sissy Virginity

We had chatted online and I agreed to meet him at his place, I was ready to take the step to live action and he was very hot and hung. I arrived and he led me to the bathroom to get dressed and made up, "See you in a few,Sweety" he said, I was already feeling gurly just by the sweety remark. I put on my cutest pnk plaid school gurl skirt, white stockings and pink satin panties, made up my face with some very hot red cocksucker lipstick, eyeliner and blush. I was so nervous, yet so horny. I took...

2 years ago
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Island of Hernando Rodriguez

He watched them as they sat sipping their colorful drinks and flirting with male guests and hotel employees alike at the Garden Cloud Lounge. They were undoubtedly four sisters, all in their late twenties and thirties, and attractive. They were obviously American, and they laughed as they tried what little Spanish they knew on the young waiters. He had seen groups like this many times. Their often affluent husbands allowed them to have "Girl's Time Off" now and then. It worked out on both...

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