Sexy Cousin Dee Loses Anal Virginity
- 4 years ago
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It was Christmas Eve and Mona looked smoking hot. To appease her parents, she went to church with them around 6:00 pm-- but she was sure to dress to the nines in an outfit that made the entire congregation pray for her soul. To top it all off, her long dark hair was styled in soft curls and her lips were covered in dark red lipstick
When the service was over and dinner consumed, she headed out to a pub to meet up with her friends. When she got there, she noticed that she was the last to arrive, as everyone was already piss-drunk. Her ex-boyfriend, Bill, was sitting at a table with a group of his pals. She sauntered over, remembering at the last moment that it happened to be his birthday today, too.
Everyone calls him Wild Bill. He is about six feet tall with short brown hair and a wide smile. He has almond-shaped eyes, tanned skin, and a dark, soft beard that always looks like four-day-old stubble. He bikes or skates everywhere, so he has a strong, lean stomach and thick thighs. The first time they fucked, they destroyed his entire flat-- they came in seven different rooms (including outside on the front porch) and devoured each other until the sun came up. He was a skater, a boozer, and a rabbit in the sack. Just her type.
“Happy birthday, Billy!" she said, greeting him with a kiss on the cheek.
“Mona, girl! Looking good. Come, have a drink with us.”
They made small talk during their first round. She found out that he was in town visiting his family (as he had recently moved across the country) and he was happy to be celebrating his own birthday and Christmas with his friends. Mona sucked down another vodka soda and found that she couldn’t stop smiling. She remembered how much he made her laugh and how much she enjoyed looking at him. While they had broken up years before, the sex was so good between them that they often ended up going home together on nights like these.
“Do you want some speed?" he asked, holding out his hand and presenting a small capsule.
“Yes”, she said as she took the little pill and threw it back her throat. She instantly recognized that it was going to be a very long night between them.
Right before it kicked in, Billy whispered in her ear, “All I want for my birthday is to eat you out all night. Seriously, I want to have my tongue in that delicious pussy of yours for hours.”
She laughed and kissed him hard on the mouth. “Let’s get out of here, then!”
They didn’t bother saying goodbye to anyone at the pub-- instead, they walked straight back to her flat, making out along the route. They pushed each other up against walls, cars, and stop signs while exploring each other’s tongues and bodies. The speed was really starting to hit, making both of them particularly randy and sensitive to all of the heavy and hot groping. Luckily, it wasn’t a far walk.
Together, the pair rushed up to Mona’s bedroom. After practically throwing her onto the bed, Billy undressed hurriedly as she did the same. They were both completely naked when he drove head-first into her pussy.
His tongue worked its magic on her clit for hours.
He rolled his tongue over her entire vulva, exploring her labia and soft, sensitive folds. He lapped at her clit and bit it softly. He stuck his tongue deep into her and swirled it around. At other times he plunged his fingers into her warm cunt, probing her with his strong fingers. She liked when he licked and fingered her at the same time. She opened her legs wider and wider for him, letting him have a glorious view and access to every inch of her private oasis.
Mona came again and again, which was surprising considering she was on speed and typically couldn’t cum when she was so blasted. But Billy’s tongue knew exactly how to please her and he was relentlessly licking, sucking, and flicking her most sensitive parts for the better part of the evening.
“I fucking love this pussy”, he said, smiling up at her while she grabbed that back of his head and played with his hair.
Occasionally, she would pull at him, imploring him to fuck her with his hard, beautiful six-inch cock. He would eagerly pump into her for a few minutes, but true to his word he would stop before long so he could taste her sweet pussy again.
At moments, his tongue was firm. At others, it teased her softly and playfully. His teeth were used to nibble her clit and lips softly. His tongue started to rove over her thighs, then back to her clit, then down to her lips and vagina, before suddenly she felt his tongue at the rim of her anus! She was so surprised that she jerked, but he held her down firmly with his strong hands and arms. What the fuck, she thought, why is he licking me there? Isn’t it dirty? What if it smells or tastes bad? OH GOD, why does this feel so fucking amazing?
Mona had never had someone lick her ass before. She only had a finger in there once or twice, but she was a complete anal virgin besides that. Billy’s rim job felt so incredibly magnificent, though, that she was instantly turned on to the idea of more butt play. Thankfully, Billy read the signs and he quickly inserted a long finger into her dark star. Cum slid out of Mona in response.
Damn, I am so turned on. Oh. My. God, I don’t want this to ever stop. Merry Christmas to me, she thought as she found herself closer to orgasming.
Billy put in another finger as he continued to eat her soaking pussy and lick her horny ass with abandon. Her juices were all over his chin and cheeks; her legs were wrapped tightly around the back of his neck and back; her hands were holding onto the bedpost for dear life. Never, ever have I felt this good, she considered to herself again.
“Flip over on your stomach and get on your knees...I am going to claim your ass!” he declared with a laugh.
“What! No! You know I have never done that! I don’t want to-- I can barely take two fingers.”
“Mona, girl. You’re so wet and turned on right now. You’ve been grinding your ass into me every time I get close to it. We have lube. You’re gonna love it, I promise."
Mona rolled over. He was right, she finally wanted to get fucked in the ass. She wanted to participate in this raunchy, taboo sex act more than anything. She stuck her ass a little up in the air and waited for the assault.
Billy took the lube from the side table and started to cover his throbbing cock with it before pouring some onto Mona’s ass. It was cold, but it otherwise a wonderful sensation. Using his fingers, he worked the lube and her own juices into her tight star, continuing to stretch and loosen her dirty entrance as he lubricated and prepared her for this new level of debauchery.
“Relax your muscles,” he said, slapping her on the buttcheek abruptly. “It won’t hurt as bad if you relax. The good news is, I know you’re super turned on by the thought of my dick in your ass, you little slut.”
God, he is right. I want this so bad. “Yes Billy, fuck me in the ass. I want you in my ass”.
Slowly, Billy started to thrust into her. Mona winced as his cock nudged up against her closed entrance. It’s never going to go in, fuck this, it hurts. Oh god, it hurts so bad, I hope this is over soon, she silently prayed to herself. To distract herself from the pain, she started to play with her own clit.
Billy took his time, too. He let Mona adjust to his girth as he gradually drove his entire shaft into her star, so his balls were pressed up against her warm, soaking cunt. Then, ever so slowly, he started to pull out so he could reenact the same assault. Her body twitched and she whimpered softly. He paused before slowly pulling out some more. After sluggishly pushing in and pulling out a few more times, Mona finally began to relax. Then, she started to moan and mewl.
“Oh yes, fuck my ass, Billy! Fuck my ass! This feels amazing!”
Encouraged by her words, Billy began to ram into her. Her tight canal was milking his dick. He was so turned on by the persistent and strong muscles that gripped his shaft that he screamed “Fuck yeah!!” as he held onto her hips and slammed his body up against hers, his balls slapping wildly at her other entrance. Mona found the entire situation intoxicating and she was nearly delirious with pleasure when he reached around and started to flick her clit. She felt even wilder as he embedded two fingers into her opened pussy.
"Claim my ass, Billy! My ass is yours!" Mona screamed.
After a few moments joined in pleasure like this, he pushed her closer and closer to the bed, letting the weight of his body crush her into the pillows and mattress. He used his knees to force her legs completely together so her ass would be even tighter around his throbbing cock. Getting up on his knees, it only took a few more rough, steady pushes into her tight hole before Mona howled in pleasure from the absolute-best orgasm she had ever experienced. In response, Billy released a warm, sticky load deep into her ass. He left his dick to soften a bit before he slowly pulled it out of her abused asshole. He collapsed on the bed beside her and gave her a sloppy, wet kiss the lips before they both fell asleep in a tangled embrace.
The end.
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Going back a while ago I really wanted to know what it be like to be fucked. So.. I logged onto a gay social site and arranged a meet. I ended up going to this guys flat. He was around 40ish. He showed me in and we went straight to the bedroom. I was slightly nervous at the idea. But, hell I was here now. We had an awkward conversation then went to it. He began to kiss me. I responded and soon it was tongues. Feeling around each others mouths. I went and grabbed his cock. It was already...
Hello ISS readers. I have been a silent reader for around 5 years now. Recently, I wished I could share my own story of losing my virginity to my boyfriend. I am Udita residing in Bangalore, India. And I am a native of a small town in Surat, but for the sake of my career, I am here. I have always been a shyly sexually active person ever since the time I discovered about sex during my early teenage. Pleasing myself through masturbation has always been a satisfaction to me. I am presently 22, and...
One of my first stories written, this is a true story…. one of many fine memories… My encounter with Mona… I first met Mona in August, a few years ago… when I was riding a beat as a police officer. I was working 3rd shift, from 10:30 pm till 6:30 am. One evening around 1:00 am I was making my rounds and pulled into one of my all night 7/11 Stores. As I walked in and said hello to the clerk I saw her standing with her back to me. She was playing a video game against the window, opposite end from...
Mona Lisa Life By Heather St. Claire and Troy X "What the -- " The man known to the world as Bob couldn't figure out what was going on. One moment, he had been sitting alone in his apartment, reading the latest TG fiction on his computer; now he was someplace else. It had happened in an instant, in the blink of an eye. He was standing on the street in a city he didn't recognize. It looked like any place in small town America in the year 2003. A main street that must have once...
(In 2005, Troy Xavier and I co-authored a story here called "Mona Lisa Life," about two TG fiction fans being transported from the early 21st century to the middle of the 20th century to assume the lives of two small-town young women, who were raising two young daughters. There were many generous reviews, and several requests for a sequel. Here's a long- delayed response to those requests.) Mona Lisa Life: December '63 (Oh, What a Night) By Heather St. Claire The wrapping...
HistoricalOne of my first stories written, this is a true story.... one of many fine memories...My encounter with Mona...I first met Mona in August, a few years ago... when I was riding a beat as a police officer. I was working 3rd shift, from 10:30 pm till 6:30 am. One evening around 1:00 am I was making my rounds and pulled into one of my all night 7/11 Stores.As I walked in and said hello to the clerk I saw her standing with her back to me. She was playing a video game against the window, opposite end...
Straight SexAnna Smith was introverted. She had no friends and often was by herself. She was very awkward around people. Anna had just turned eighteen and was in her last year of high school.She never was invited to parties and didn’t really have anybody she could say was her friend. She was a virgin and had no experience with boys. She had crushes on many boys in her class and a man crush on her male teachers. She was too shy to make conversation with anyone.She spent a lot of time at home and did a...
IncestHi. I am ‘that guy’. I am 26 and average body with a 5.5-6-inch penis. Since I received positive feedback about my previous stories, I am writing about my experience from college. This story is in 3 parts. The first and second parts are about how I got to have sex with two roommates and the third part is a surprise package. Make sure to read them all. The story began when I was in the final year of my college. I had a classmate named Aarti who was also my good friend. We used to study...
Despite needing sleep after the long week of torturing herself, Sarah woke up around 4:00am the next morning and laughed when she saw the clock. Her panties were wet as she recounted the great sex from earlier in her head. Knowing she wouldn’t be able to sleep so worked up, she got out her vibrator and got off again, followed by grabbing her phone and sending a text to Mr. Michaels, “Your devoted cum whore is now addicted. I just came for you again Master. Please get out of my head and let...
My name is Lori. I have been carrying the shame of what I did, and what happened to me, at my bachelorette party with me for 5 years. The guilt and shame are almost unbearable at times. I have thought about telling one of my close friends or my sister, but have never worked up the courage to do actually do it. I am thinking about going to a counselor just to talk about it with another person, while maintaining confidentiality. The only people that know this story are me and the guy that was...
Carlo had awoken after hearing moans coming from his sister Kelly’s room. It was around two o’clock AM, and her moans became quite loud. Carlo was already nude and moved his hand up and down his semi-erect cock. He knew his sister must have been pleasuring herself again with her hairbrush. He was going to knock on her door and tell her he could make her feel amazing. She could either say yes or no or slap him across his horny face.Kelly was getting louder by the minute, and then there was...
IncestAnna Smith was introverted. She had no friends and often was by herself. She was very awkward around people. Anna had just turned eighteen and was in her last year of high school. She never was invited to parties and didn’t really have anybody she could say was her friend. She was a virgin and had no experience with boys. She had crushes on many boys in her class and a man crush on her male teachers. She was too shy to make conversation with anyone. She spent a lot of time at home and did a...
“Night, Jason. Have a good Christmas!”“Night, Kim. See you in the New Year!”I smiled to myself as I left the office. Almost as timid as I was, Kim was as alluring as ever, her shy smile warming my insides.I’d been working there for nearly a year now. Eleven fabulous months with five of the most perfect colleagues you could ever have! Things had really worked out for me. Again…Quite surprising for a shy introvert like me. I was doing remarkably well.‘How so?’ I hear you ask. Let me explain. I...
Group SexIt was Friday night and again I was thinking about Heather. I couldn't stop daydreaming about last week with her. That cute little blonde's tight ass was so incredible. Tonight Heather was going to take her next step into the world becoming a slut, only she didn't know it yet. She was in for quite a surprise. Christine and I had it all planned.We wanted Heather to realize that we were now in total control of her sex life. We wanted her to know that from now on she was our sex slave and was...
My name is Sarah, I have what I guess you would call a petite body – though it is still developing. I have short dark hair and green eyes. I have barely any pubic hair (and none when all this happened) my breasts are small but firm, and my nipples are unlike the rest of me, quite large. I’m just twelve but this all happened a year ago. The story of how I lost my virginity. I managed to get into an adult only chat room and would try to join in – for some reason no one would talk to me as I...
Hey, guys, it’s Mick again. For the people who didn’t read my first story please read and give your valuable response about it. I am a 20-year-old student studying in Mumbai. I basically hail from Pune. I am 6 feet tall with an average body. I would like to thank all the readers who have read my story. After talking to Neha, I was feeling a bit irritated by her going. I wanted to use her as much as possible. I always wanted to fuck in the anal. I just used to be thrilled by thinking of anal...