Free Sex Stories
Page 1772

Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2271  |  
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THE OTHER DAUGHTER

It was like a moment frozen in time: my white hand tightly gripping my belt buckle as the other and came down on her perfect, quivering brown ass. It struck with a hard, sharp smack, and she cried out in pain, her knees sliding apart slightly. She was kneeling on her bed, her face buried in her pillow, her firm, round pointed butt up in the air. She wore only a green tank top which had become bunched up near the top of her ribcage. I delighted in being able to see the bottoms of her deep honey-colored breasts... and her soft, naked butt which now had one long red mark on it... and her nearly-h... Continue»
Posted by sexaddict66 3 years ago  |  Categories: Mature, Taboo  |  Views: 3117  |  
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Landlady needs attention

When I was in my twenties I was lodging with a few guys in a house owned by a recently widowed lady. she was quite a large lady and very down to earth...
Anyway, one friday evening I arrived home from work a little early. She was alone in the house and the other guys had gone away for the weekend...
I entered thru the back door as usual. I could hear the tv. as i came to the lounge doorway i could see her in her armchair facing the tv. She obviously didnt hear me come in because as i was about to say hi she leaned back spread her legs a little and slid her hand up her dress, letting out a li... Continue»
Posted by SurfEd 3 years ago  |  Categories: Hardcore, Mature  |  Views: 4458  |  
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My first time...

When I was s*******n I went to stay with my uncle's f****y in California for three weeks. Mainly I was visiting my cousin Vicki who was sixteen at the time. Toward the end of my visit Vicki's friend Ashley, who was s*******n, dropped her off at home after they were done with school. Ashley came in to meet me and hung out for few minutes, then went home.
Later my cousin told me that Ashley had called her, raving about how cute I was after she left. I kinda laughed it off, I had fooled around with girls before, had a couple of non-serious relationships, but nothing serious and was still a ... Continue»
Posted by Titfucklvr 3 years ago  |  Categories: First Time  |  Views: 1842  |  
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GRANDMA AND A CAMERA

My grandmother was always around when I was little. She always would pick me up from the bus stop, always buy me stuff, etc. Ever since I was 12, I noticed her differently. I saw how large her boobs and ass were and often fantasized about her naked and me sucking on her nipples and fucking her pussy. She was about 5'6, 300 pounds, 34d breasts, and long hair. 

By the time I turned 13, I would watch her undress through the keyhole, but she was always in a bra and panties. I had never seen her completely naked. I often jacked off thinking about her, and shoot my cum high into the air. A few mo... Continue»
Posted by jkjkram 2 years ago  |  Categories: Fetish, First Time, Mature  |  Views: 2944  |  
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Daytona fun

I was sitting in traffic on main drag at the 5 o'clock jam in my F-150 with my windows down. No sense in being at the beach without the salt air blowing on you. I heard a noise coming from behind the truck and i looked in my passenger side mirror. It was a boy, or young man on skateboard coming along the sidewalk. He passed the truck and kind of caught my eye, medium length sandy brown hair parted to one side, white wife beater shirt and a lightweight long sleeve shirt covering it and tan shorts that went below the knees. His face was well tanned and i could see a bit of ab muscle through th... Continue»
Posted by jmsseal46 8 months ago  |  Categories: Gay Male, Hardcore  |  Views: 1960  |  
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Best Summer

I could not believe how this summer started. I tried to a big jump on my bicycle the first week out of school and crashed. I broke both my wrist and had cast on from hands to my elbows. I could not do anything, not even hold my dick to pee. Mom took off time from work to help me.
After a few days the pain wore off but the cast keep me from doing much. Mom had to help me do everything. It took some getting used to. The second week mom thought I should have a bath as I was starting to stink. She ran the tub and undressed me. I was pretty excited for her to see me as I had hair on my balls ... Continue»
Posted by zimabean 1 year ago  |  Categories: First Time, Hardcore, Mature  |  Views: 3117  |  
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Club Cuckold

Rick's hands griped the steering wheel so tight that
his fingers were turning red. He was looking for the
address he'd printed out from the welcome package the
club sent him last week.

Jen sat nervously on the passenger side of the car
trying to see the address's on the buildings as Rick
slowly drove down the street.

"It's the next building, Honey. Turn into the next
driveway."

Rick eased his foot on the gas peddle and turned into
the next driveway. The address on the huge red brick
building matched the one he was given on the
informatio... Continue»
Posted by creampielover 4 years ago  |  Categories: Group Sex, Interracial Sex, Voyeur  |  Views: 2825  |  
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My Half-s****r & Me

My Half-s****r moved in with Mom and me when I was 13 or 14, she was 19. I had met her only once, when I was 7 or 8, so I really didn't
know her. Mom worked the 3-11pm shift, so we were home alone in
the evening. One night I was stroking my cock to a playboy when my
s****r (Linda) came walking in and caught me. I had covered myself
with the magazine and Linda walked over, sat on the edge of the bed
and said "It's okay, if you want, I'll do that for you." Well, hell why
would I pass up my first opportunity for some kind of sex, whether it
be a handjob or wh... Continue»
Posted by strangerknocking 4 years ago  |  Categories: Taboo  |  Views: 10414  |  
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step s****r love

Introduction: true storybout me and my step s****r. i want your comments andopinions on it please its my first story

step s****r love

so this is a true story about my step s****r. whos fucking hot as hell by the way. i know alot of guys wish they could have there step s****rs...well i did.

it started a very dull and boring day. all of us k**s were playing outside like any normal day while the parents were out shopping or what ever they do. we were all havin a water balloon fight and that was when i noticed my step s****r for the first time. a little bout her her name is brandi and om... Continue»
Posted by marioxtz 2 years ago  |  Categories: Fetish, Hardcore, Taboo  |  Views: 3959  |  
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Cum drenched Mom in the middle - An Adult Story

I woke around 1pm. It was the first day of my summer vacation. My parents had left early in the morning. They left some money on the kitchen table, the night before.. They were leaving for three weeks. I could not get time off from my part time job. I worked about 4hrs every Sunday at a gas station. I told them I might pick up more hours now that school was done. My parents were happy. I only took the part time job, so I would not have to go to church with them on Sunday’s.

They were kind of religious. They forbid me to do just about everything. They would be mad if they knew I ... Continue»
Posted by thebigboobbbwlover 4 months ago  |  Categories: First Time, Group Sex, Taboo  |  Views: 4460  |  
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DAUGHTER'S BIG DADDY

I just turned 18 and had never had a boyfriend sad but true. My mother had died shortly after my 14th summer and since then it had just been Daddy and me. He tried his best but never could fill her void. I never really got the whole dating thing and kissing and everything like that. I think having a mother could have helped in that area. Daddy kind of discouraged it anyway. I think he was just overwhelmed by the responsibility of being a single parent. He spent a lot of time at the gym working out. I think that it was his way of dealing with the loss but it left me very lonely.

I started ta... Continue»
Posted by famlover66 3 years ago  |  Categories: Mature, Taboo  |  Views: 4082  |  
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I Love My Wife

I awoke to the most heavenly sight. My gorgeous wife Kate was sitting next to me, slowly taking my cock in and out of her mouth, alternating between licking my sensitive pereneum and gently stroking me. "Good morning baby", she said, with the most gorgeous eyes and smile. I love when she wakes me this way. Kate is 5 ft 7 in, and weighs about 125 lbs. She has sandy brown hair, with a gorgeous face and skin, eyes, the whole package. A great ass, stomach, legs, and some of the nicest natural c cup breasts I have ever seen. Sound too good to be true? Well, its true. I am a lucky bastard, and for s... Continue»
Posted by ryand1979 3 years ago  |  Categories: Anal, Masturbation, Taboo  |  Views: 3488  |  
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First Encounter With A Ladyboy

A couple weeks ago I met this fine girl walking down the beach. Looked a little asian, but maybe she was one of those latina aztec chicks that just look asian. I go up and talk to her, shes got a really sweet voice, tells me her name is Jazz. I start talking with her about where she lives. Tells me she lives a couple blocks away and she tans all day long next to her pool. I look at her.. and damn shes right, cuz she has a really nice golden tan. I ask her "well why are you at the beach? "Cuz Im tired of tanning and not showing off my body to anyone!" I say, "oh well that definitely makes sense... Continue»
Posted by bnrslyr 2 years ago  |  Categories: Anal, Shemales  |  Views: 2904  |  
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BREAKING CURFEW

I looked up the side of the house toward my bedroom window. It was closed and the d****s were shut. I left both the window and d****s open when I broke out at nine o'clock to escape being grounded and meet my boyfriend Pete so we could try out his new motorcycle. We spent the whole night with friends racing on the flats outside of town; opening up the engine to see what she could do. Five minutes ago, I made Pete let me off at the corner down the street so the bike's muffler wouldn't wake my dad. So much for that idea, I thought, kicking over a landscaping stone at the edge of the flower bed. ... Continue»
Posted by sexaddict66 2 years ago  |  Categories: Mature, Taboo  |  Views: 2631  |  
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Bad Husband Learns What's Good For...

It's not that I hate my husband, on the contrary.

He does annoy me sometimes. His inability to stand up for himself at work, at home.

However, when we're out and about, amongst our friends, shopping, or amongst strangers, he has the tendency to put me down.

We've discussed before that it aggravates me to no end. That he should be respectful to me at all times, and not belittle me to try to make himself seem cooler or more interesting.

Those conversations don't seem to matter. Time and time again he's done it. Time and time again I attempt to correct him.

My husband, Matt, is by ... Continue»
Posted by bi_hengst 11 months ago  |  Categories: Fetish, First Time, Gay Male  |  Views: 2570  |  
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My Virgin Ass

Since i posted my last story (should I??) where i finally admitted to myself that i wanted to suck a nice big hard cock, i've got quite a few messages from other members gving me their views on what i should do.

Most pm's were encouraging me to go thru with it, telling me how much i would enjoy it, that it would change my life, that there is nothing like the feel of a hard cock exploding in your mouth. Well sadly I still have not gotten the guts to do something about it...........but i will!

I have had a bit of a sexual awakening thanks to these messages. One man convinced me to have a c... Continue»
Posted by thetbone 2 years ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1359  |  
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THE FLU

I shivered as the flu tore at my body. My father held me close as I moaned and cried and wished I could just sl**p it off. His body was the only warmth I could feel in a world that had, suddenly, become so very cold and barren. I shivered, pulling my body closer to his nakedness, not caring for a moment what might seem wrong to others, I was for once warm. He held me close that first night, took care of me every time I wanted a sip of water.

I know he was naked, but I do not remember seeing him that way as he made countless trips to the kitchen to get me juice every time I was thirsty. I do... Continue»
Posted by sexaddict66 2 years ago  |  Categories: Mature, Taboo  |  Views: 2574  |  
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first time making love as a gay man ( true story o

One day me and a friend were coming home from a badass party, and boy were we smashed. When we got back to my house my friend chris told me about how he had experienced gay sex with a friend. He went on about how it feel far better than a women. As my friend was talking i started to getting really horny. " chris?" i said, " i know this might sound weird but ive always wanted to try it with a guy". we agreed not to tell any of our other friends about it. we were both a little skeptical about the idea because we both have never had anal with a man. we agreed to flip a coi... Continue»
Posted by sexy420 4 years ago  |  Categories: Anal, First Time, Gay Male  |  Views: 1028  |  
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Fantasy for Hubby!

The notion of getting married had never crossed my mind before I knew Alex; after all, I was just 18-year-old when I met him; besides, my mind was actually preoccupied mostly with two things, traveling and painting. I was dreaming of visiting Paris, London, and others of those magnificent places. That was probably the reason I became infatuated with Alex, because he was interested also in traveling.

On the other hand, it occurred to me--due to what I saw from my b*****rs, friends, and my older s****r husband--that men aren't really interested in woman as a person. They're more int... Continue»
Posted by kabeer69 4 years ago  |  Categories: Taboo, Voyeur  |  Views: 2044  |  
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