Free Sex Stories
Page 4

it started in the office: chapter 1

Sandra sat at her desk and read the email over again. "My dear Sandra, I had such a good time with you last night that I wanted to send you a little thank you note. Your company was wonderful, and well, after, well, I have to say that I have never been with such a kinky, and generous woman before. You are truly amazing....... Leanne."

"Now that is an interesting call back," Sandra's boss Amanda suddenly said as she leaned over Sandra's shoulder to hand her a cup of coffee.

Sandra blushed, and hard. Though she had never made it any secret that she was a lesbian, she had never revealed an... Continue»
Posted by pussyeater3300 2 days ago  |  Categories: BDSM, Hardcore, Lesbian Sex  |  
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First Night Out as a Sissy Pt 2 (By Crystal_ed)

So picking up where I had left off from my last published story…. I had just ventured out for the first time as sissy, determined to find a man. I went to a local sports bar dressed in in my tightest jeans and favorite panties and teased a group of guys. Was able to get one of them into my car for my first blow job ever and after swallowing his enormous load, his friends busted us before I could know the pleasure of him inside of me. After being busted (but feeling sweetly naughty) I was going to call it a night before I realized the bar tender still had my card because I hadn’t closed my tab.... Continue»
Posted by Crystal_ed 2 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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In Püblic



I began my
transformation from regular boy into cock suckking teenage crossdresser.

we were having a really hot heat wave here in philadelphia; my mom wanted
me to get out of the house and off the computer so she suggested a movie.
I felt wierd going to the movies by myself but I really did want to see
that inception movie. I looked up when they the theater opens up and was
surprised they had a 1030am showing and it was a cheaper price which was
good for me. Being on summer break from school and not having much luck
finding a part time job I was short on money. I did not want ... Continue»
Posted by klammer 2 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Submissive

Now I have a very feminine side and have always been interested in men,
however, being married and from a small mid western town where they called
guys interested in men queer, fags, well you know all the derogatory terms
the straight laced populace use. We had moved to Florida for the purpose
of a job that I had applied for and after two interviews actually landed.
I found that even though the city we had moved to was more of a large town,
the community didn't come down so hard on guys like me. I have always
ignored my interest in men, but over the years have been approached by men,
... Continue»
Posted by klammer 2 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Birthday

It was supposed to be the best day of my life...and maybe it was, but
definitely not in the way I planned.

My 21st birthday...my first day as a man, as a true lord of the Manor...my
first day as a Master. I was so nervous I threw up my lunch. Not very
manly, I know, but just the thought of having my very own sissy to play
with had me teetering between the giddy excitement of a k** right about to
open the biggest present under the tree, and the stark terror of officially
being a man in my step-father's eyes...how could I measure up to him? I
felt destined to disappoint him...and I did... Continue»
Posted by klammer 2 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Meeting my Neighbor

I live in a small but growing city, but most everyone (including me) is on the DL so there's never a lot of action. I saw a post on Craigslist last night from someone in town. Since I couldn't get away I figured it was a missed opportunity, but I emailed him anyway hoping that maybe we could work something out another time. I was pleasantly surprised when he emailed me back this morning, and he was still looking and could host. He was only a couple blocks away, too.

I made my normal excuses ("going to get some exercise") and walked over to his house. He met me on the porch and we chatt... Continue»
Posted by boernesucker 2 days ago  |  Categories: Anal, First Time, Gay Male  |  
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Nervous

I have never been so nervous in my entire life, what the hell was I
thinking?!

Before I start there, let me take you back a bit and describe myself. My
name's Sal and I'm kind of a huge pervert. I've got short black hair and
I'm 19 years old, 5'7" and 150lbs. I'm pretty small all in all, but because
I cycle a lot I've got nice thick legs and a bit of a bubble butt.

Back to me being a pervert. I'd never been with anyone before, so I was a
total virgin. I'd recently been getting my rocks off online looking at
crossdressing and bondage pics. I'd recently started buying linergie, sex
... Continue»
Posted by klammer 2 days ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Late Night Visitors

It was nearly midnight as the three men walked through the campsite on their way back from the pub. It was an early Spring moonless night with a chill in the air so they were walking at a brisk pace, chatting and joking in low voices along the way. One of them happened to glance to the right and noticed that a caravan in the near distance was rocking.

“Look!” He exclaimed, pointing at the caravan.

“There’s fuckin’ goinig on on in there in there!” Said the second.

“I know who’s that is,” said the third, “it’s Mike and Mindi!”

Mindi was a long legged, big breasted, dark haired girl i... Continue»
Posted by C4690 2 days ago  |  Categories: Group Sex, Voyeur  |  
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I've been learning to smoke! Part 2 - The Rev

So late last night my hubby sent me a quick text from the airport to let me know he'd landed and would be home in about 45 mins, I sent one back to say I couldn't wait to see him, I'd really missed him. Then a few minutes later I sent "To be completely honest, it's your cock I've missed most, I hope you're not tired because I'm gonna need to feel it in all my holes tonight!" Followed by "I'll be upstairs waiting, be naked and ready for some fun when you come up"

I got a quick thumbs up text back so I went up and got ready, chose some dark makeup to accentuate the roll I planned to play, got... Continue»
Posted by volupval 2 days ago  |  Categories: Fetish, Hardcore, Taboo  |  
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Fuck on a public beach

I love taking my girlfriend to the beach. Her big tits were always pushed up to a quite pleasant angle by the shape of her bikini top and her bottoms clung to her round bum in a way that turned the eyes of everyone who could see it. So as we lounged on our towels in the hot summer sun I could not help but stare at her rubbing lotion on her smooth, sexy legs. I found myself fantasizing about kissing up and down them till I reached her…

“Babe?” I heard her voice say.

I pulled myself out of my thoughts and gave her a smile, trying to hide the slowly growing erection my fantasies and her voi... Continue»
Posted by BiCoupleNY 2 days ago  |  Categories: Hardcore, Voyeur  |  
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My first abuse and humiliation

I can't see, my nipples are on fire and my throbbing cock is being teasingly stroked, all's well.

I don't get to cum without my partner and due to an extremely busy week with no physical contact I'm extremely pent up, my balls are full and my mind has been utter filth for the last 4 days. In our time apart I am permitted, no, encouraged to touch myself, edge, tease, but never cum. That is her semen, her orgasm and her property between my legs, but she always likes to have her fun before I get my release.
I answered the door in just a dressing gown, she kisses me and smiles, quirking an eye... Continue»
Posted by damage_case 2 days ago  |  Categories: BDSM, Fetish, First Time  |  
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I like to tease

I was sitting on the couch when my boyfriend got out of the bathroom. He informed me he was going to bed and I should too since it was late. I still needed to do some work so I said I'd be staying up for a while longer but I'd get to bed as soon as I can. I ended up not being able to go to bed until 3 hours later. When I finally stripped off all my clothes and climbed in he was fast asl**p. He's almost always the one to initiate sex but I was feeling horny tonight and he was passed out so I decided to take it in to my own hands.

I slid my hand under the covers and down his chest to his stom... Continue»
Posted by luvsitrough 2 days ago  |  Categories: Hardcore  |  
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Castle: Girls Gone Wild Gone Wrong

Alexis Castle peeked in on her Father in his study. “Bye Daddy. I’m going out with Janie and Debbie. Don’t wait up.” Her Father didn’t look up from his laptop but mumbled, “Sure sweetie. Have fun.” Alexis smiled. She knew she shouldn’t expect too much when her Father was in the zone. He was almost finished with his latest novel and was so focused, a bomb could have gone off and he wouldn’t have noticed. The other thing he didn’t notice was how his 20 year old daughter was dressed. The cute redhead had on a very short skirt, crop top and six inch heels. It was also very obvious that s... Continue»
Posted by rider2005 2 days ago  |  Categories: Anal, Celebrities, Lesbian Sex  |  
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Camping with Chris

Me and a couple of friends were cruising around, trying to find someone to get us high for free. Kevin suggested this gay guy that had lots of money and liked to buy large quantities of cocaine in exchange for company. Both me and Chris instantly said no. Kevin pointed out that we had nowhere else to go and plus there was three of us and only one of him. If we watched each others back there was no way anything could happen. We agreed and next thing we knew a average height slightly overweight guy in his 40s was driving us in a pickup truck with a camper shell to a popular local camping ground ... Continue»
Posted by Disticles 2 days ago  |  Categories: Gay Male, Taboo  |  
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My photo-shoot with Susanna Francessca

This story about a photo-shoot with Susanna Francessca was sent to me by Brian. Thanks, Brian.

“Kevin, it’s so good to read stories about Susanna Francessca and to see pictures and videos of her. I did a photo-shoot with her at her photo-studio with her and it was fantastic to see her getting naked for my camera. I just wish I’d shot a video of her, stripping off. What a girl !!!!!

It was the first time I’d booked a topless model and I was nervous as hell. I mean, how was I going to build up the courage to ask her to take her bra off? I just didn’t know. But, I shouldn’t have worr... Continue»
Posted by KevinGraves2 2 days ago  |  Categories: Masturbation, Sex Humor  |  
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Cuckold Teen 2

As I started to cum, Tasha opened her mouth and pearl white sticky cum streamed from my rock hard cock into her mouth, there was a heavy load and it started to trickle out the corners of her mouth. "Hold my cum in your open mouth" as I again grabbed my phone and opened the camera, a few photos then video, ensuring that Stuart was in no doubt how hard she had been face fucked, her mascara had ran down her cheeks and this little cum bucket had a mouthful of my cum in her mouth "swallow my cum you little slut and tell your pathetic boyfriend hoe it tastes" I commanded, Tasha gulped my cum and eve... Continue»
Posted by lovelong 2 days ago  |  Categories: First Time, Group Sex, Taboo  |  
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My wife's gets her pay back!!!

I was working out of town for a couple weeks, and my wife was not happy. When I got home we kissed and then she told me to go shower. When I got out of the shower she was wear some sexy lingerie that showed off her beautiful thick body and all her curves. I was getting hard already. I walked up and tried to put my arms around her, she stopped me and told me I had to be punished for leaving her for 2 weeks before I got to touch her. She sent me to our room.

Once in there I saw a tall guy in just his underwear. He was skinny and had no body hair, baby face, and looked about 20. I didn't know ... Continue»
Posted by Bifreakycpl 2 days ago  |  Categories: Anal, Gay Male, Hardcore  |  
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My CD GF wants to be treated like a lady

Sammie is my TG/CD girl friend. Let me tell you about are last hookup. I made a date to take Sammie out for dinner on Valentines day. I asked her to geo all out dressing up, makeup clothes boots the whole nine yards. She loved the idea and said yes. I made reservations at a very nice restaurant, it's dimly lit and the music is very low and soft. I like that so that we can speak softly and romantically to each other. I picked up Sammie at 8 sharp. My God she was beautiful, her gorgeous red hair shone, her makeup was perfect, I loved her eye shadow and this really dark shade of pink lipstick. He... Continue»
Posted by Lossst 2 days ago  |  Categories: Fetish, Shemales  |  
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Caught By Mr. "D" - Part 4

I assumed my thing with Mr. D was over and done with. I left for college with only girls on my mind. My first year ended and I came back home for the summer.

One weekday afternoon I was alone in the house and I decided to go out back to read a book. This time with all my clothes on (see Part 1 if you haven't yet...)

Mr. D interrupted my reading when he walked over from his house next door. There were a few seconds of initial discomfort but that passed quickly. We were both glad to see each other. We started to chat and then Mr. D got right to the point:

"This is totally up to you an... Continue»
Posted by blacktopchaser 2 days ago  |  Categories: Gay Male, Group Sex, Interracial Sex  |  
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The Purge

Funny thing about Crossdressing, the love of the silk, the satin, the lace, can be balanced with most intense feelings of guilt. Then in a fit your clean out because you are going to go straight. Clean up your act all that stuff. So bags of carefully gathered items are consigned to the waste bin of life. Unfortunately, as I have progressed through life I have realised that crossdressing and association with womens lingerie is not a phase, it is just part of me.

Alright, I admit it – it’s a sexual thrill. It’s not a desire to transition or anything like that. It’s the joy of obtaining th... Continue»
Posted by paddy57 2 days ago  |  Categories: Fetish, Masturbation, Taboo  |  
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