Category: first times

Assfucking 101

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I was an 18 years old college freshman and living in a coed dorm. I was also quite a shy kid and didn’t know very many people in the dorm but I did make friends with the RA. She was a 21 year old Puerto Rican senior pre-med major. Since I was also pre-med, she sort of took me under her wing when I came to the school.

One evening I was preparing to take a shower, so I slipped on my robe and was walking down the hall to the showers. The RA was standing in the hallway, she complimented me on my robe, which was a black, silk robe that barely came down to my knees. It was a high school graduation gift and since I never used a robe at home, I had no other robe to use, so I used it despite the many jokes from the other guys in the dorm that called me Hugh Hefner whenever I wore it.

Well I thanked her for the compliment and she said “before you take your shower I wanted to give you that book you were asking me about, however, I am about to go out so come and get it now.”

I said “Ok” and followed her, actually I was walking behind her staring at her soft ample behind. She normally dressed down with sweats and t-shirt but tonight she had on a tight black dress with her hair and make-up done to perfection.

As I walked in her room, I noticed that it wasn’t in its usually state of student disarray but neatsome may even have considered it clean.

I said to her jokingly, “expecting someone over?”

She said “yes.”

“Ok, let me get the book and go before they get here, I said.

She said, “it’s over there on the desk.”

So I went to retrieve it. As I did, she closed the door. This was strange because anytime myself or any of the guys in the dorm was in her room, the door was to remain open, university rules.

So I got the book and was about to leave when she said, “do you like me?”

“Sure,” I said naively, “I like you a lot, you have been a great mentor.”

“No,” she said, “I mean if you had the chance, would you want to sleep with me?”

Now I was completely stunned, here is this gorgeous woman and she want to know if I wanted to have sex would her, was she crazy, of course I did, shit, I had sex with every day in my fantasies.

So I said, “Uhh…yeah…uhh, I think so.”

I was scared as hell not knowing what to say or do next. She told me to go sit on her bed and told me to lean back.

“Don’t be nervous” she said, “I like you alot and I think we can be real close.”

She then began to kiss me. She kissed me more than I kissed her because I was still shocked. She saw how nervous I was and asked if I was a virgin.

I said “no,” which was technically true, I did have sex one time with my old girlfriend but she chickened out midway through so I never came. But I did penetrate, so I wasn’t a virgin. I don’t think she believed me.

She said “I going to treat you real nice, we can take it nice and slow.”
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Webcam Fun

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Matt was a pretty cool guy. I had chatted with him online for over a year now, and due to the distance between us we hadn’t met each other yet. He was a computer tech based out of Silicon Valley, and I was an Administrative Assistant living in Florida. However, that was all about to change.

Matt had it all. He was smart, good looking, funny, and a good friend. Our chats had started out completely innocent. Mostly stuff like ‘how was your day’, and, ‘ what do you like to do for fun’. As months passed by, though, our chats became more serious. We had discussed everything from what we want in life to how many kids we’d want to have. Also, around this time, our chats got a little more risqué. We began exchanging fantasies and having cybersex.

We had done everything that people do when they first chat. Exchanging pics back and forth. As in our chats, the intial pics were purely innocent. Pics of us with our friends, at the beach, of us with our families. Normal stuff. However, just like with our chats, our pics became less and less innocent. From me in my lingerie, and him in his boxer briefs…to nothing at all. We eventually got to the point where we would specify how we wanted each other to be positioned in the pics we were taking.

About a month into our chatting, we had both decided to purchase a webcam. Unlike the chatting and the pics, this didn’t start off innocent. We knew exactly why we’d each purchased the cams, and what we wanted to do. I told him for my first inital act, I’d like to perform a striptease for him. I told him the song I was planning on stripping to, and how we could, through online microphones, be able to hear each other while performed.
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Joe and Me

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My husband and I had been fantasizing about me having sex with a client of his. It was brought up basically in jest, but we talked more and more about it as time went on, and it eventually became a favorite fantasy of ours. Well, one day my husband had a prospective client in his office, and the client (whose name is Joe) looked at a picture of me my husband has on his desk and remarked on how lucky he was to have such a beautiful wife (as the author of this story, I can refer to myself however I want!).

My husband agreed with him, and asked him if he wanted to see a better picture. Naturally Joe said yes, and my husband showed him a more revealing picture that he has of me. I’m coming up out of a pool, wearing a white one-piece swimming suit. Thanks to the water, the suit left very little to the imagination. When Joe expressed his appreciation, my husband took the bold step of asking him if he’d like to have sex with me!

So that’s basically the background. I’m sitting at home when my husband calls and asks me if I’d like to join him and Joe for dinner. He asks me if I remember what our favorite fantasy has been, and if I’d really be willing to go through with it. I remember being shocked that HE was willing to go through with it, but I was basically aroused by the whole idea of it. So he told me to put on something sexy and meet them at the restaurant.

I quickly jumped in the shower to get ready. Yes, my hands did wander as I got all soaped up and thought about what I was about to do, but I didn’t really masturbate all the way to a climax. I was just sort of moving around in a heightened state of arousal. I put on a pair of thong panties, a very revealing bra (to accentuate my firm, 36C breasts), stockings, garters, a tight black skirt, 3″ heels, and a very tight gold top. The top was high cut, but so tight that it just molded around my breasts. And I was so aroused that it was very easy to see my nipples through the shirt. I knew I would be turning some heads. Finishing with some make-up, I was out the door to meet the boys.

As I drove, I was wondering what the client would look like. In our fantasies, he had naturally been an incredibly studly guy. When I found the two of them at the bar, it was quite the opposite. Joe was about 45, balding, and really quite overweight. But I was committed at this point, and as I walked up to meet them I could feel his eyes surveying my body, which did have the effect of increasing my arousal despite the way he looked. I had a drink with them at the bar (okay, I had about 3 drinks actually, figuring I’d need to be a little drunk to really go through with this – but who’s counting?). It was actually sort of fun flirting with him and making my husband squirm, and I made sure to do a lot of touching him, both with my hands and brush-ups against my chest. My horniness was increasing.
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Fun With David

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My story started when my wife, Bonnie, and I, began to bring our individual fantasies into our lovemaking. Our sex life had become routine, so this was a way to enhance, as well as vary, our sexual relationship. I, like so many other men, get very turned on with the idea of sharing Bonnie with someone else, male or female, so I was usually the instigator of these fantasy sessions.

Bonnie is about 5‘3“, has very sexy, though average sized tits, and has an ass to die for. Though having given birth to 2 kids, she still looks as hot as ever to be 40 years old. Being the conservative wife when it came to sex, she was usually a willing participant, but most of the time it took some coaxing on my part to get her into the fantasy games. It was almost humorous at times, how she’d deny being interested in actually going through with our fantasies, but while we acted them out, she became insatiable. She seemed to especially enjoy fantasizing about fucking a stranger while I joined in. During sex, Bonnie loves to use a vibrator or dildo while sucking my cock, so it’s a pretty good indication of what her true desires really are; though she refuses to admit it. Often, as we are making love, I ask Bonnie if she would fuck a stranger if he walked in the room right then. Most of the time, she would say “no“, that it was only a fantasy, but sometimes, when she was really turned on, she would say “yes“.

So, it was with this little tidbit of knowledge, that I set about hatching my plan. I knew it would be a huge risk, but regardless of the outcome, I knew our love for each other would remain steadfast. Our kids had made plans for the upcoming weekend, so I knew Friday night was wide open.

My plan was to blindfold Bonnie, tie her to the bed, and bring a “stranger“ into the bedroom. Bonnie usually enjoyed the helplessness of being tied up during sex, but the blindfold was certainly going to be an obstacle, as Bonnie is very claustrophobic. I would just have to figure out a way to make her give in.

We live in a fairly small community, so the means of finding a stranger, such as an escort service would provide, was out of the question, and I was hesitant to pick up just anyone to take part. The only solution was to bring a friend, and I knew just who it should be.
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Nice Day At Work

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The rain had started and business was slowing down as we headed into our off-season. I was scribbling notes in the personnel file, trying to figure out how to avoid big staff cuts through the winter. I knew some hours had to be slashed, but I always hated doing it. I must have looked to be in a sour mood, because the whole staff avoided contact with me other than the routine hellos and brief exchanges needed to run things. I rolled my chair away from the desk, trying to unjam my brain, and looked out the window at the will call counter

She had worked for us for 4 summers – ever since her junior year of high school. She was a cute kid then, but was just now starting to lose that teen baby face. In its place, she was beginning to take on the look of a strikingly beautiful woman. She let her auburn hair grow a little longer than usual this year, just a few inches past her shoulders, and when she was close by I could smell the lightly sweet fragrance of that soft hair every time she brushed it with her fingers or turned her head. Despite my strict rule against personal relationships with anyone at work, I had quite a crush on her. I was cautious to be professional in her presence trying to avoid being obvious, or create the impression that she was given any preferential treatment.

I never thought she would stay with us for so long, but I was glad she did. She was smart, friendly and customers liked her. She had just returned from a trip to Vegas with her fiance for her belated 21st birthday and I found myself taking more and more chances sneaking glances at her gorgeous body. Being a fan of a curvy backside, she was a constant reminder of what a perfect womanly ass looks like. I recalled pieces of a conversation I overheard between her and another female co-worker as they shared stories of what their respective boyfriends did (and didn’t) do for them sexually. My mind drifted back to it lazily.

“Great!”, I thought to myself, “On top of everything else – now I’m horny as hell.” I gathered myself and made my way back to the desk. If there wasn’t the sound of people talking in the break room and hallway nearby, I probably would have locked my door and given myself a quick jerk to relieve the tension. I cursed my own open-door policy and tried to get back to the pile of to-dos on the desk. It took awhile, but I got back into my work groove and managed to be productive the rest of the afternoon.

I hadn’t looked at the clock for quite some time – apparently a few hours – and was surprised to hear myself saying my daily “goodbyes” to the night staff as they left. I leaned back in my chair, closed my eyes and stretched my arms over my head when I caught a familiar scent.

“Boss?” said a low voice, startling me from my stretch. I looked over to the doorway and she was standing there leaned against the jamb with her hands in front of her – twisting and fiddling with her fingers nervously. “Can I talk to you a sec?”
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Taking Care Of The Pool Man

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A lot of people don’t realize, but frosted glass is see-through. Only when it is daylight outside does it work as it is supposed to. If its night, and you turn a light on, anyone outside can see straight inside. My wife and I found this out a few years ago, when a female neighbor came and told us we should close the curtains on our bathroom, as she could see right through our window as clear as anything. Apparently she had a nineteen year old son who was having a good time looking through our window at my wife soaping herself in the shower, and no doubt bending over to put her knickers on as well. The thought of some pimply teenage boy pulling his hardon while staring in at my trim and prudish little Asian wife in her birthday suit turned me on no end.

My wife is Malay, and generally is very careful about covering her body and would never even step outside in shorts. But surprisingly, she wasn’t that worried about having been seen naked by some horny young man who no doubt came all over his hands while thinking about what it would be like to stick his sausage in my wife’s tight little cunt or bumhole. She felt if he had seen her like that, that was just his good luck and she hoped he enjoyed himself. This got me thinking, and I said to her, “Well, if you leave the blinds up, and some poor guy gets all hot and bothered because of it, then the next time that happens I think it’s only fair that you take care of it for him.” Feeling myself get hard, I told her that she must promise that if any guy ever came to the door and said he had seen her naked in the shower, she was to pull him in through the door, apologize and ask if she could take care of it for him. The she would drop to her knees, unzip his fly and pull his cock out and take it in her mouth, bringing him off. Shocking, my wife agreed to all this, although I of course just assumed that she was playing along with my fantasy and the situation would never actually arise. It was many years later that I realized how wrong I had been.
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My First Threesome

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Our first threesome was the greatest sexual turn on I have ever had. A friend of ours that came over just about every weekend was who I had my eye on.

Steve would come over, and my husband and I would drink, smoke, and talk on the ham radio till late at night. Steve would all ways hit the road about 2 am, and my husband and I would go to bed. This had gone on for about 3 months, but this evening he didn’t have a ride home, so my husband told him that he would take him home. Just as he was about to leave I called my husband back to the bedroom, and ask him what he thought about Steve going to bed with us. He was really shocked, but it was so sexually arousing that he loved the idea.

Now he had to get up the nerve to ask Steve what he thought, they got in the car, and just as they pulled out of the drive way, my husband, somehow ask the question, Steve was all for it.

They backed the car,into the drive and got out. My husband said he was getting so nervous that he was about to freak out. When they came back in the house, my husband ask Steve if he had any more of that smoke with him, he said yes, and pulled it out, My husband came back in the bedroom and ask me to come out and join them in a few tokes, I said Oh yes.

We sat and talked for about 30 minutes while we smoked and got a real buzz on. I said, I’m going to go get in bed. They followed me back to the bedroom and we all sat on the bed. We talked a little more as I took off my robe. I said, come on guys get your clothes off and get in bed. We all took off everything but our underwear and got under the covers, I ask Steve if he would light up another jay, and as he did I got up and got an ash tray, and slid back under the covers.
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Cheerleaders First Time

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It was a chilly night in November, the football team sucked a big one but Mike just went to hang out with his friends, and watch 18 year old Stacia cheer in front of the stands. She was beautiful. They had known each other for as long as they both could remember. High School had been harsh on both of them. Stacia had just got out of a long term relationship and Mike had just had a few short-timers.

Stacia was still a virgin, an extremely sexy one. She was about 5’6” tall and probably about 105 lbs. She had beautiful blonde hair just past her shoulders, and the smoothest, sexiest tan legs. One of the things that made Mike squirm the most was Stacia’s lips. Her lips were perfect. Mike had fantasized about her lips since he started fantasizing about anything.

It was halftime and Mike decided to go get a drink at the concession stand and he saw Stacia standing alone at the back of the line. Mike joined her and they talked a little bit about what was happening with people at school, just the latest gossip. Just before Mike was about to return to his seat Stacia told him that she did not have a ride home from the game, her mom had her car for some reason, so she needed a ride. Mike happily agreed and returned to his seat.

After the game Mike went to his Chevy Blazer and pulled it up to the exit from the stadium and waited for the beautiful blonde, slim cheerleader. After about 5 minutes of watching her talk with some of her friends she skipped to the vehicle.

“Hey! I’m ready”, Stacia said as she got in the car. Mike started down the road and they listened to the radio and talked some more. Finally, Mike decided this was the time to admit his—for lack of a better word—crush on Stacia.

“You know, Stacia, I’ve always wanted to tell you what I think of you”

“Yeah? Well what do you think?”, she said with a smile.

“Well, you’re just so nice to everyone and so beautiful, and I’ve always admired you, you know, ever since I’ve known you I guess.”

“Awwwww, Mike”, she giggled a little bit, “I know how you feel.”

“What do you mean by that?”, he said with an anxious look.

“Well, I’ve felt pretty much the same way about you for a long time”, she smiled.

“Really!?”, he exclaimed in surprise.

“Yeah”, she said blushing a little.

“That’s really weird, I expected to get shot down or laughed at, this is great!”

She giggled a little bit and thought about what was happening and told Mike that she was a little bit hungry. They talked about their newfound emotions for each other as Mike drove to Sonic. Mike bought Stacia what she wanted and he just got a Coke.

Stacia lived out of town on a dirt road, so Mike started that way. It was about a 20-minute drive from where they were. Stacia took some ketchup and smeared it on Mike’s face.

“Hey! What the…”

Stacia giggled as Mike turned his vehicle onto the dirt road, “Oops, it looks like you have something on your cheek.” Stacia leaned over and slowly licked it off.

Mike shivered and pulled over. He turned his head to her and softly kissed her lips. He had been hauling something in the back of his Blazer earlier that day, so he had the back seat folded down. He remembered this and motioned for her to crawl in the back. He followed close. They laid down facing each other and he kissed her again. She slipped her tongue between his lips and he massaged it with his. Mike slid his hand around her waist and pulled her cheerleading skirt up and put his hand on her ass. With the other hand, he slid it under her right side and pulled her on top of him.

Stacia rested her body on Mike’s waist as they passionately made out. Mike placed both of his hands on her beautiful ass and massaged it. Stacia’s hands made their way to the top of Mike’s hands and she squeezed, too.

Stacia stopped kissing him and bit her bottom lip as she slid his shirt off him. Mike slid his hands up her cheerleading top and slid it off. She was wearing a white sports bra underneath. With one hand he helped her slide her bra off and with the other he massaged her slightly damp, tight virgin pussy through her cheerleading panties. She slid her hand down and helped him massage her pussy, and at the same time she unbuttoned his jeans.

Once she had them unzipped, she slid her body down and pulled his shoes off and then his jeans. She slithered back up and Mike couldn’t take his eyes off her beautiful body. Stacia slid his boxers down and off and began to work his cock, which was as hard as a rock by now, with her hand. Mike stared at the ceiling of his Blazer while she jacked him off slowly. His breathing picked up and finally he looked down to see that the lips that he had fantasized for so many years were about to take his cock between him. His heart rate increased in anticipation and finally she slid his cock into her mouth and started to suck.

Mike could tell that Stacia had some experience in this field, and he was grateful. Stacia slid her head up and down on Mike’s cock, taking in as much as she could handle and sucked with all her might. She used her hand to massage is balls. Stacia took his cock out of her mouth and licked up and down all of it’s sides and licked down and started to suck and lick his balls, one by one. This put Mike over the edge, he began to moan loudly and breath extremely hard. She jacked him off hard as she worked his balls with her mouth. Mike ran his fingers through her beautiful blonde hair. Stacia licked back up and took his cock back into her mouth and kept jacking it off. Finally, Mike shot the most violent load of cum he had ever unloaded, deep into her throat. She swallowed it happily and smiled at him.

Stacia crawled up his body and rested on him and kissed him.

“Stacia, baby, that was unbelievable”

“He he, Mikey, it’s not over”, she told him.

This made Mike’s cock grow for the second time nearly instantly. He reached around Stacia’s cheerleading skirt and unzipped it. He crawled up on top of her and went down and slid her soaked panties off. Mike began to lick her tasty wet virgin pussy and she began to moan loudly. She grasped his hair in both hands as he slid his middle finger into her pussy until he brushed up against her cherry. He smiled. Mike began to work her pussy with his middle finger as he took her clit between his lips and worked it with his tongue and lips. After a while, Mike licked his index finger and tried to slide it into her wet pussy. He was amazed to find that even thought she was so wet, he could not get a second finger in her!

Mike realized that his cock was at least the width of three of his own fingers. He wondered how hard it would be to open up this virgin hole. He licked and fingered her until she screeched and came all over his fingers.

Mike crawled up on top of her and kissed her passionately as he slid the bottom of his cock up and down on her clit. Then, he rested the head of his cock at the opening of her pussy and stared deeply into her eyes. He slowly slid the head of his cock into her pussy and she started to moan. He worked the head in and out of her about 10 times before he slid another inch into her. She moaned louder. After another 10 pumps he slid the rest of his cock in, feeling her cherry tear apart.

Stacia screamed loud and grabbed Mike’s ass hard. She felt a tear roll down her cheek, and didn’t bother to wipe it. She could feel his massive cock slide into her pussy. She felt him fill up her tight hole. She was overcome by pain and pleasure and she didn’t care about anything but Mike’s cock filling her up. She moved her hips up to meet Mike’s cock. After a good 5 minutes of Mike working her. His cock was all the way in her.

Stacia breathed heavily and looked into Mike’s eyes, trying with her hands to pull him in deeper. Mike left his cock as far in her as he could get it for about a minute, he moved it a few millimeters every few seconds. Finally, he pulled it out all the way and slid it back in. Stacia rested her head on the floor and stared up. Mike pumped her pussy very slowly. Stacia was moaning loudly.

Mike was so amazed at how tight her pussy was. It wrapped around his cock like a glove, a very tight glove. His eyes rolled back into his skull. The pleasure her tighter than tight, recently virgin pussy was bringing him was 20 on a scale of 1-10. He began to pick up speed, sliding his cock deep into her and back out. He could hear her moaning loudly.

“Mike! Go faster baby”, she cried out.

Stacia could feel the pressure every time he slid his cock into her. She moaned loudly every time he reached the limit of her depths. Stacia met Mike’s pumps by moving her hips every time. She started breathing more heavily and slammed her body up bringing his cock deeper than it had been before and she cummed hard, covering mike’s cock.

Mike could feel her hot cum all over him and it took him the rest of the way. He slammed his cock deeper into her a few times and shot his load deep into her tight pussy. She screamed and moaned as Mike collapsed onto her petite, tan, beautiful body. She kissed him all over. Mike lay there breathing heavily, catching his breath while Stacia patted his cock as it softened. Stacia’s pussy leaked cum out all over. The windows on the vehicle were fogged up all the way. It was really late.

Stacia and Mike got dressed and they finished their trip back to Stacia’s house. Once they got there, Mike kissed her passionately and she told him to come over tomorrow. Mike smiled and drove off; he was the happiest man alive.

Stacia couldn’t believe how wonderful it felt having Mike’s cock deep inside her. She couldn’t wait until tomorrow when Mike would come over.

About Anna

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It’s nearly 8 PM and I’m sitting here in a pissy mood. I agreed to go to the mountains with Jane and a couple of her friends this weekend. Jane’s sister has come down with the flu and needs help with the baby while her husband is away on a business trip. So here I am waiting for Peter and Anna to pick me up for a two hour drive to the mountains. What put me in a pissy mood is the fact that I don’t really like Peter and Anna. Well Anna is okay. She’s pretty and sweet, but Peter is absolutely boring. He’s 21, an ultra conservative and always has everything well planned. He and Anna have been going out since high school. They’ve come to the same college and are getting married this summer after graduation. I might as well be going off for a weekend with a 50 year old couple.

I could see his car approaching. In an instant my mood did a 180 degree turn. I could feel that little rush that runs up your spine and finishes in a smirk, joyful smile. A thought raced through my mind. I’d fuck Anna this weekend. No, I wouldn’t just fuck her, I was going to FUCK her.

As he pulled up, the trunk unlatched. I threw my bag in, and slid into the back seat behind Anna. We exchanged greetings and condolences about Jane. Then, as he started to drive, he told me about the weekend.

“Too bad Jane had to cancel, we’ll have a great weekend. We’ll head off tomorrow morning about 9:00 so we should be at the trail head by 10:00. It’s a good 3 hour hike to the summit but a bit faster coming down. So I figure we can hang out and have some lunch on the summit until 3:30. We should be back at the car by 6:00. I’ve reserved a table at the restaurant in town for 7:30 so we’ll have plenty of time to get back.”

Somehow I managed an inattentive response. “Great. Sounds like you have everything planned”.
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Frat House Party

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Sylvia had come to this particular frat party to get fucked – and getting fucked she was! Fed up with bad dates that went nowhere and relationships where her heart got broken, she’d decided that right now all she needed was a good hard fuck. She hadn’t even particularly cared who it came from, just someone who wasn’t going to leave her with a broken heart at the end of it. It had been almost 6 months since she’d last had sex and she intended to make up for it now.

The guy on top of her was actually one she knew, his name was Chris and she’d seen him around campus before. A year older than her at 22 he was a little drunk but still very excited to have this gorgeous leggy girl come up to him and start blatantly making out. She’d chosen him because he was cute and rumored to be one hell of a lay, and when they’d gotten up into bed she’d also found that he had a rather sizable dick. Right now all of it was buried in her twat, making her burn with pent-up lust as he fucked her hard, the bed was shaking he was laying into her so good. Moaning loudly she wrapped her legs around his waist, pulling his thick meat deeper into her pussy.

“FUCK ME! FUCK ME HARD YOU BASTARD!!!” She screamed as she started cumming… the door to the room banged open and two more guys were staring at her getting her brains fucked out. That didn’t stop her orgasm though, it kept going as she screamed her ecstasy at the watching guys; they were grinning as Chris gasped and buried himself into her convulsing pussy, spilling cum into her body. Gasping happily as the guy collapsed on top of her she looked at their viewers.

“Can I help you,” she asked, as dignified as she could be with a dick shrinking inside her body.
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