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Painkillr

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- When I Was A Kid -
Straight Male / 53

High School

Looking back at some photos from high school made me realize how exposed I was for most of it. From the time I entered high school when I was 14 until I graduated when I was 18 I was on the swim Team. We wore Speedos made of very little material and they were very snug.

Seeing the pictures now showed me how much of a very clear idea of what your junk was like without actually being naked. I can see the outline, size and shape of all the teams cocks as the Speedos snuggly wrapped around us. Being that we had been in many competitions we had easily been seen by thousands of spectators. I had been seen naked in the change rooms by the others on the team, the coach and some of the mothers. During away competitions some mother would come along to help and they would come into the change rooms afterwards where we dressing and showering. Seeing the photos now makes me feel like I was pretty well naked in front of everyone when I wore my Speedos.

There was never anything sexually said or done when wore the Speedos or were naked in the change rooms when the mothers were in there except one thing that occurred pretty regularly during our early morning practices.

After our early morning practices we would go into the change room and take a shower. There was one teacher who always very conveniently, right when were we were showering and naked, would come in asking if we knew where our coach was. She would then comment on how well our practice went and usually begin talking about other things. Sometimes she was only in there for a minute and other times it was a lot longer. There we were a group of 6 teen boys between the ages of 14 to 18 showering naked as a female teacher was in there watching us. The older guys on the team mentioned she has been doing this for a couple of years. They asked if I had her as a teacher, which I did. They told me she likes seeing us and not to worry as it will get me better grades. I just accepted it and followed along with what the other guys did.

3
# 60006 - by A / August 7, 2022
- When I Was A Kid -
Straight Female / 50

Dream Come True

Here I am! My name is Danielle, but people just call me Dani. I am a 48 year old woman, married with 3 kids. My husband and I have been together since high school. We have a great relationship and a very healthy sex life. We know all about each other's sexual fantasies and history. But he doesn't know this story about my first sexual experience. I've always kept it to myself, for myself.

My first crush was the woman who lived down stairs in our basement. Her name was Linda. Linda was 21, young and beautiful, voluptuous and very sexy! Linda lived by herself. She worked as a waitress and sometimes she would tend bar at one of the local pubs. So she was usually home during the day. She would sunbathe in the yard and she would let me hang out with her on her blanket. We would talk about boys and makeup and listen to music. I thought she was so cool and worldly. When Linda would be dressed to go out on a date, she looked like a movie star. I would watch her leave and dream about what they were going to do. I was so jealous! I wanted to be her.

One day Linda looked at me and said "You're pretty tall. I think we're the same height. What are you? 5' 2"? She then invited me down to her apartment and she let me try on some of her things. She put makeup and perfume on me. She said "You don't look 13 anymore!" I felt so grown up and glamorous. She told me I looked like a girl she used to date. I was astonished. I couldn't believe she dated girls too! I asked her if she dated girls a lot. She said a few times. She told me that she was bisexual. I've thought about girls but in the eighties that was taboo, especially in a predominantly Italian Catholic neighborhood. I could never tell my friends from school that I ever thought about a girl in that way. Linda begged me not to tell my family. I told her I would never and swore I wouldn't.

That night laying in my bed I couldn't get the thoughts of Linda with another woman out of my head. I tossed and turned in my bed. I couldn't sleep. I then noticed that my panties were extremely warm and moist. I felt flushed. I lifted my night shirt up over my little pot belly and my B cups with my puffy nipples and put my hand between my legs. I had masturbated before but it never felt this incredible. I played with myself as thoughts of kissing her and holding her naked body ran through my head. I didn't want it to end but then I had the most unbelievable orgasm. When I was done I put my juicy fingers in my mouth and I sucked on them until I fell asleep. I dreamt about her all night.

The next day was a beautiful and hot summer day. I knew Linda would be sunbathing today. When I looked out the window in the backyard, she was in her bikini, putting the blanket down and she looked up and saw me. She smiled and waved for me to come hang with her. I was so excited I ran down the stairs and took them two at a time! She made lemonade for us. It was awesome. Just as I started to take off my shirt and shorts to show her my new bathing suit, my mom came out and said that we needed to leave and go to the store. I was so upset! I wanted to cry. As I started to put my shirt back on Linda told my mother that I could stay with her. Usually my mother would never let me out of her sight. Before I could turn and beg my mother to stay, Linda said we were just going to get some sun, listen to music, she even said she'd make me lunch. My mother said that she was going to be gone all day. She asked Linda if she was sure. Linda said no problem at all. As my mother said ok and turned to leave, I'll never forget what Linda said "Don't worry, just two girlfriends hanging out enjoying this beautiful day!" I was beaming after she said that, I couldn't stop smiling! I never felt like a little girl when I was with her. She always made me feel older, like her equal. Just another reason why I loved her!
We were having such a good time. We were listening to Prince on her boom-box. She introduced me to his music. I became the biggest Prince fan! We were reading magazines like Vogue and Rolling Stone. This was starting off to be such an amazing day!
Linda turned over to lay on her stomach. She asked me to put oil on her back, and the backs of her legs. As I poured the oil in my hand she untied her bikini top. I was so excited and nervous that I poured too much oil and spilled some. I kept saying I was sorry. She laughed and said "Don't worry about it. It's cool. It's an old blanket anyway." She really put me at ease. I started to spread the oil across her shoulders and down her back. My barely teen loins were starting to rev up again like they did last night. My bathing suit was getting soaked. As I got to her amazing plump bubble-butt she pulled her bikini bottoms down just a little bit. The top of her butt crack was showing. I let out an audible gasp. She asked "Did you spill more oil?" I just shook my head no as I continued to rub oil on her back dimples and on her butt as I touched her crack. I was starting to breathe a little heavy. Linda asked "Are you ok?" I just nodded my head yes. My mouth was dry and I couldn't speak. Linda then told me not to forget her legs, especially her thighs. I knelt down by her feet and I grabbed her ankle with my oily hands and I ran my hands up and down her calves. I then poured oil on her thighs and I massaged the oil in. Linda cooed "Oh yeah that feels so good". When my hand slid up her inner thigh my finger touched her pussy through her bathing suit. I didn't know if I was sweating from the sun or my arousal. It was probably both. Once I was done Linda said "Come lay next to me."
I asked Linda "So, how was your date last night?" She said "Oh with Tommy?" as she rolled her eyes. I asked "What did you guys do?" Linda looked at me and smiled and then giggled. "Do you really want to know everything?" She asked. I just nodded my head with a big grin on my face. She said "Ok well, he took me to this beautiful Italian restaurant. It was very romantic and very dark. We sat in a booth in the corner. Tommy had his hands all over me. He was a decent kisser. We had some wine and then we had our dinners which were nothing special. As we waited for our dessert, I figured I would have my own dessert. I snuggled up next to him and put my hand between his legs. He was hard and he was huge! I couldn't wait to taste him. I needed something sweet. I crawled under the table, unleashed his beast and I gave him a mind bending blow job! You know...?" I said "I think so" Linda said "It's when a woman sucks a man's penis until he cums." I asked her "What is cum? I heard it mentioned in a joke at school. What's worse than grease on Olivia Newton-John? Cum on Eileen. I pretended I knew what it meant but I didn't get it." Linda chuckled as if she heard the joke before. Linda then said "Cum is semen. The thick white goo that comes out when a man has an orgasm. It's what gets a woman pregnant when they have penis to vaginal sex." I just nodded and said "Oh yeah..." I didn't really know what she was talking about but I wanted her to think I did. Linda then took a sip of her lemonade. Then she said "After that, we had the tiramisu. Then, when the check came, Tommy started to frantically look for his wallet and guess what? I said "What?" Linda laughed "The dummy forgot his wallet and couldn't pay the check. They wouldn't let him leave. I wasn't going to pay and I wasn't going to wait for someone to bring him the money." "What did you do?" I ..(continue confession)

1
# 60034 - by DD / August 9, 2022
- When I Was A Kid -
Straight Male / 26

Mom Hired A Maid That Would Give My Brothers And I Blowjobs.

I have 3 brothers and we are all withing 4 years of eachother. I'm an Irish twin with my older brother (born within 12 months of eachother) and my younger brothers are legitimate twins, 2 years younger than me. When we got to an age where all of us were masterbating probably 3+ times a day, our mom was probably shattering socks when she did laundry.

I dont know which of my brothers did this one, but they were fucking the area between couch cushions and my mom had a talk with us after that.

A couple weeks later our old maid was replaced with a much younger white maid. She was a brunette and had very small breasts and was very skinny. At the time we wernt thinking past the tip of our dicks and I thought she was the hottest chick ever. I've seen pictures of her recently and I was definately blinded by horny.

My mom would leave to go shopping whenever she came over and the first time she was ever there, the maid told us "I need to stop you boys from making messes. I'll go in the bathroom and you guys line up and take turns coming in and I'll help you." My oldest brother went first and we couldn't hear much over the sound of the fan but we did hear her say to take his pants down along with some grunting. About a minute later he came out and we could see her kneeling in the middle of the bathroom. I went in next and i'll never forget the sensation of her fingers against my lower abdomen as they slipped into my shorts and boxers to pull them down. A tingle sensation shot through my whole body and I was already about to cum. She told me to tap her head when I was almost done. She wrapped her lips around my dick and I saw her head slide down onto my cock and by the time she got to the base of it, I was Cummings. I tapped her head, she sealed her lips and I drained myself into her mouth. When I was done she slid her mouth off, and spit my load into the toilet. I was in shock and didn't really know what to do so I just said "thank you so much." She laughed and said "your welcome" through a giggle.

She came over every week for a few months and we performed the same little blowjob train. Sometimes we would get back in line after and go for seconds once we got more used to it. Our mom would always leave the house and at that age we though she was a fool for leaving us home alone with this maid and that we were being sneaky. Later it clicked that she knew (and probably paid) for exactly what was happening and just didn't want to be around for it.

2
# 60037 - by Cptcumsalot / August 9, 2022
- When I Was A Kid -
Straight Male / 43

Mrs Smith

When I graduated HS I was coming off football and track and field throwing event seasons, and was going to continue the throwing events at our local university. I was muscular with very little body fat, best shape of my life.

I had always been close to my aunt and uncle, he had done very well in rental houses and land purchases around town, from nothing to a multi-millionaire. They lived in a beautiful house in a gated subdivision and belonged to the local country club. I hung out at their house a lot, one because we had always been close even before the money, two, it was a beautiful place, and three because my aunt was a dark skinned gorgeous MILF who enjoyed going braless a lot and seemed to have more than a normal interest in me, but that's another story.

I had gotten my lifeguard certification at Scout camp a couple of years back and my aunt asked me if I would teach my cousins to swim. They were good kids and relatives and she was going to pay me for a couple of hours of work 2-3 times a week, which was more than I would have made at my 8 hours shifts nearly full time at the big box store I had worked at, so it was a no brainer. Not to mention I'd get to see my aunt jiggle around in her skimpy swimsuits a lot.

After a couple of weeks, my aunt asked me if I minded meeting them at the country club pool so she could talk to her friends. I was fine with it, they were mostly doctor and lawyer trophy wife young MILFs lying around the pool in barely anything drinking wine all afternoon while their kids played in the pool.

After a few weeks my aunt pulled me aside and said "some of my friends were wondering if you could teach their kids to swim too?" Most of them had mansions with pools like my aunt, some wanted me to teach them at home, some at the club. Easy money, MILF t&a, it was a dream gig. So I would take 2-3 famillies 3 times a week.

About midway through the Summer Mrs Smith (not her real name) asked me to teach her kids. She was a leggy blond with full pouty lips and a 34D natural chest. She was married to a doctor who seemed to always be gone. She asked me to come by a couple of times a week to teach her 2 kids.

She would always park herself by the pool in a skimpy bikini and polish off a bottle of wine by the time the lesson was over. I would catch her looking close when I would get out of the pool. I purposely started wearing unlined trunks that when they got wet would cling to me and show off the cock, which always seemed to be hard around her.

The feeling was mutual, I would stare at her as she would sun herself, her suit left little to the imagination. Her top was so skimpy I could see the edge of her nipples in the suit, and her thong bottoms showed off her perfect ass. She would catch me staring at her, I wouldn't look away, and she would just smile.

After a few weeks she started asking me if I would rub oil on her, of course I said yes, and the more weeks I did it, the more bold she would get. Like asking me to rub it on her thighs and parting her legs a little, undoing her top and having it down further on the sides. It was so obvious, it was clear she was enjoying it. And my cock proved I did too.

Finally one week I went over and went in the backyard to the pool like normal. She was laying out and the kids were gone. I asked about them and she said her husband had taken them to visit their grandma out of state and were gone for the week. I said ok I'll see you next week and she said no, its ok to stay I'll still pay you for the week. We laid out for a little bit, she had already taken down her first bottle of wine and started on the second.

She asked me to oil her and as I started and she untied her top and raised up and pulled it out from under her saying "I dont want to get oil on this its brand new. You dont mind do you?" Of course I didn't so as I was doing her back she would raise up slightly to slide her side boob up more to my hand. When I finished, she turned over and said could you do the front?

I was pretty shocked although it was hard to not see it coming. I was nervous because this had never happened and I didn't want to get in trouble and blow a good gig. I started to rub oil on her tits, not believing my good fortune. She pulled me down and kissed me and said let me rub some oil on you.

We switched places and she dumped a huge amount on my chest and legs and started working them over. As she got to my waist she pulled down my trunks and said we dont need these and pulled them off and squirted oil on my cock and started stroking me. I stopped her after a couple of minutes because I was already about to explode. She said "lets go inside I need some more wine" and she grabbed my trunks and headed inside leaving me naked to follow with her topless.

We went into a room and she got an old sheet and spread it on the bed and got some baby oil and we took turns oiling each other up. I took off her thong and she had a faint landing strip over her pussy. She took my hand and put it down there and started moaning. I knew there was no turning back so I started rubbing her, then licking. She started moaning more saying no one had licked her for years.

She pulled me on top of her and guided my cock inside and said "ooohhh gaaaddd" and started pulling me deeper inside her and humping me saying she hadn't been fucked in months. Apparently her husband had a side piece and was having an affair, she later told me this was her way of paying him back.

I started pounding her, I knew I wasn't going to last long seeing her big oily tits jiggling around. She's screaming I'm cominggg!!! and I'm doing everything I can to try to slow down and not cum too quickly. Finally on her second or third orgasm I couldn't take it, I told her I was going to cum and she said cum inside me, I'm on the pill. So with a couple of strokes as deep as I could push into her I started filling her with a couple of weeks worth of cum. It felt like I came for 2 or 3 minutes, so much my balls were aching.

We collapsed on each other and laid there. I couldn't believe it was happening. She was snuggled up on my chest and started kissing me. Then about 15 minutes later rubbing my cock which was already hard again from seeing this gorgeous woman nude in my arms. And here we go for round two.

This time I took over, flipped her over on all fours and started pounding her from behind. I pushed my thumb in her ass and it set her off. She was cuming and screaming oh fuck oh fuck, fuck me harder!!!!!!!, I lasted about 5 minutes, grabbed her hips, slammed into her and gave her every bit of cum I had left. We collapsed again and laid there for about 30 minutes, then showered and talked.

She said she had wanted to do that since the first time she saw me, she said her husband made her feel like she wasnt sexy anymore and she knew he was having an affair. I told her he was crazy that she was the hottest woman at the club pool. She kissed me and snuggled in my arms for awhile, then it was time to leave.

We only had one more chance to play before my time teaching her kids was over. When we would run into each other we'd smile and give that we have a secret wink. I heard she met someone else and ended up leaving her husband for him. She definitely taught me some sexual lessons, best summer ever.

4
# 60050 - by FieldEvents / August 10, 2022
- When I Was A Kid -
Straight Female / 61

Sex Ed Class And Real Life Sex Ed Afterwards

We had a sex ed class in the 8th grade. I attended a small religious based all girls school. In those days the closest we had come to sex ed was when we got our periods. The old you are woman now, so keep your legs crossed. The teacher charged with giving us the lesson relied on a movie. Becoming a Woman, a Lesson plan for young women.

But the movie didn't work in the projector. The principle called my father, because we owned a movie theatre, and he sent my cousin who was a projectionist to fix it. And he had to nurse the movie in the old projector, while we the girls sat there with lessons on how to put a condom on, how to wash and prepare our genitals for our husbands, to remember that a husband well treated, was more willing to treat us in bed later. We had pictures, cartoon drawings, or erect penises and open vulvas, and arrows indicating the hole that the penis went into. In those days the clitoris was ignored in sex ed.

After that lesson my cousin was visiting our house and I asked him if he was embarrassed. He wasn't, he showed me his penis. I held his penis, very erect and majestic. I learned how to hold my hair back as I put his penis in my mouth, so he was well treated. I lay back with my legs open, long before I ever did that with a doctor. He poked my genitals showing me where my vagina was, as if I didn't know. But he pushed his finger in up to his knuckle. He moved his finger around until I was nice and juicy before he stuck his penis in. There was no stopping, or coitus interruptus, there was only my cousin fucking me like I deserved it. When he did pull it out and lift himself off me, I was no longer a virgin, far from it.

I got my tits squeezed, my tits sucked, my ass spanked, my butthole poked with his finger. I found out that I could be fucked like a dog, on my hands and knees and he could get it all in that way. I saw my aroused genitals with a hand mirror, and felt his tongue licking me. Of the things he did with me, the one that I pulled away from was when he spanked me. But I loved it, every swat of it. I love being spanked, it's the first step to arousal.

He fucked me, because that's the word for it. He fucked me. And I loved it. I was the first girl in my school to drop out because I was pregnant, but not the last. That old movie on a reel, given to my father and kept in a closet, is still there. From the moment I saw a cartoon drawing of an erection I wanted it.

0
# 76333 - by Helen / January 24, 2025
- If The Boss Only Knew -
Straight Male / 42

Great Times

We my wife and I have to twist the truth about how we met. We always say that it was when I was in college and she was an assistant for one of my professors. There is a slight age difference between us she still has a hard body nice tits and a peach shaped ass. She gives a true pornstar a run for her money. She is very petite but gorgeous. Very tanned only 5 foot tall. The truth is we actually met in high school I was a junior 16 years old and she was our English home ec teacher. I’d run into her walking out to football practice wearing my pants and no shirt. I am and was very muscular tall dark handsome type. Never had a problem with girls and my future wife was always nice. Il call her Nancy it’s close so it will work. Nance would chat with me and sometimes keep me after class. It started as light touching and me complementing her on her legs when she wore skirts. She often touched my arms shoulder and would rest her hand on my chest if we were talking and no one was around. I remember it was after practice and for some reason probably waiting for me she was still in her room as I was leaving the locker room. I had showered and was in shorts a t shirt and flip flops when Nancy said hi and was chatting me up. She had on this one piece dress with a very lite sweater cover thing. Pretty much covered up her tits so they wouldn’t be on full display. Again as soon as she started talking to me she put her hands on me shoulder and then my chest I took a chance and leaned in and gave her a kiss didn’t hesitate kissed me back and my hands where all over her. She closed the door turned the lights off took my shirt off and proceeded to kiss and lick my chest all the while her dress had been pulled up and her nice ass was showing and only a thin piece of red material covered her little asshole. She kissed me with intense affection and I slid my fingered in and out of her. I pulled my cock out and before I knew it she had mounted me. Face to face she smelled amazing kissing me and riding me at the same time she scared the shit out of me when she ccs me on me for the first time. She shook squirted all over me and I shot my load in her. I wasn’t done and kept hammering her for another round. This time bent over her desk I hammered away and shot my load again. From that evening on Nancy was 100 percent mine. Sometimes before school almost every day after school she would have me in her room and let me have it. Best blow jobs first woman I ever have anal to. The one thing that she did that made me go bits and till this day she still does it for me. Is that she will wear a skirt or dress have me sit down and she will sit on my cock and she does this slow grind with her hips while my cock is buried in her pussy and her pussy feel’s like it’s got suction because it makes it feel so good. She would grind like that and look back at me and the feeling and that look would make me cum so hard. My senior year was just as good as I was her TA in 2 classes so that year was spent deep inside her. Prom and graduation she let me go out and have fun and made sure that i was dating other girls. She knew I would fuck some of them and she would have me tell her how they where and what they did to me. After prom I ended up banging my date After the party I took my date home we’ll fucked and then went to Nancy’s house. She gave me a proper cleaning sucked her juices off like a champ. She would tell me to get it out of my system because once we where out and officially dating I wouldn’t be able to do what I do to those girls. 2 years later we where officially dating and soon after engaged with a kid on the way. Like I said her tanned little body was meant to be fucked and I’m the lucky bastard that gets to. It’s been a while but on occasion she would bring her meat friend from college and have me watch them go at it and I’d get my dick sucked while the other rode me. Again only with my wife’s permission. I have it so good there’s no fucking way of ruin my life. She given me the best years of my life and she says o have given her the best dick and best years of her life. Damn I love this women

0
# 76812 - by Anonymous / February 12, 2025
- Fetishes and Kinky Sex -
Straight Male / 30

Family Business

I work for my wife Jessica’s family. They the family owns a slough of local grocery stores here in the area we live in. Started off with 1 store and the dad did a great job with the business and as the family grows the business grows as long as the family works hard. I started here when I was young and met my now wife. Jess is a curvy blond thick women nice size tits and an amazing ass. She lets me duck her however I want when ever I want since she is a stay at home mom. She takes care of our young daughter. We have a great life and would never leave her. She knows that some shit happens but tells me to not bring business home. She says this because I work directly for her 2 aunts. Suzanne goes by suzy and Deanna goes be Dee. 2 sisters close in age in there early 40s. Both have similar body types both blond skinny small tits nice long legs and a nice round bubble butt. They have never been married and dedicated themselves to almost all work but do have a little fun. I was in my early 20s when I found out how twisted they where and because it didn’t freak me out I became there favorite employee and moved up in the company. They even introduced me to there Niece who eventually became my wife. Suzy did the purchasing so I dealt with her directly since I was in the back of the store in shipping and receiving. The morning was the busiest time of day and by noon things where calm and there was a few hours to burn I’d help refill or help in the office. One day while helping in the office Suzy and I after some ongoing flirting ended up making out. I was young and always horny so Suzy letting me feel her up kiss her and fingering her. After a few days of doing this she closed the door and let me fuck her in her office. But here is what would freak most people out. Suzy moaned load and while the door was closed her Sister who was the store manager had her office right next door. I though she was gone so didn’t hold back any. Lots of noise kissing licking and licking neck. I shot my load into her and sat back on her chair. Suzy got up and went to clean up leaving me in her office. I was going to wipe up pull my pants up and head to the bathroom myself when Dee walked in and just stared at me. I looked saw her and said fuck I’m toast. I said I’d get my stuff and leave when she said to not get up sit down she said. My cock is half hard on full display it’s coated with her sister’s pussy juice and my cum. Dee comes over gets on her knees closes her eyes and proceeds to lick my cock clean. Tonguing my balls cock and ass licking and finally putting it in her mouth. I was shocked and what came out her mouth was every more shocking. She has her eyes closed and is sucking me off and as she sucks me off she pulls out and licks my dick and balls she starts talking to me asking me if daddy is happy with Dee cleaning Suzies juices. Is he I was shocked and said yes daddy is very happy when I said that her intensity sucking my cock increased and was now jerking me and sucking at the same time. I’m rock hard and Dee asked daddy aka me where does daddy want to cum. I answered daddy needs to cum inside you stand up and pull down your jeans for daddy I said. She does that dees ass was nice and round and she bent over with her panties and jeans a little below her ass. I stuck my tongue in her and Dee asked again if it’s going to go in her butt or kitty. I answered Daddy will let you pick where does Dee like it the most. Eyes closed she answered it’s been a while but I started to enjoy it in my butt. I spit and slid in and wow it was tight. Unlike Suzy Dee liked it rough. Really vocal when I was done I shot it up her ass made a mess her ass cheeks where red from the hard sparking she called for hair pulling. A very difficult but good fuck. After I was done with the she pulled up her jeans and went back to her office. I wiped up and Suzy came back in. Nothing was aid and a few days later we did it again. After a few weeks I was getting some from both and we had the talk. We went to lunch got it all out we won’t talk about th road for what happened to them when they where young. We just talked about how they take care of each other and have always looked for a daddy figure to take care of them and when I took the role of daddy it made sense to let me have them. They live close to us Dee ended up pregnant I raise my son with her and my daughter with Jess. We do t talk much about it they don’t do any lesbian stuff together. I fuck each one individually and then Dee cleans up and gets fucked. I don’t ask I just know that I make great money to do what I do and have 2 sisters and there niece my wife fuck me. We all 3 and the kids are very close. Nothing in front of my wife or in front of each other. I’d never admit this but Dee is my favorite fuck she is absolutely amazing in bed and the face that she clean up and I mean everything makes it hot. Hell we even vacation together.

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# 76822 - by Anonymous / February 13, 2025
- When I Was A Kid -
Straight Female / 44

Out Of The Park

I grew up known as “the trailer trash with the big tits”. I wasn’t ugly or fat or anything. Blond hair, blue eyes, 5 foot 6, and had 34G bra before entering high school, you’d think everyone would want me. However, I was poor, couldn’t afford the expensive clothes and accessories so I was picked on a lot. The girls were probably jealous, I told myself. It didn’t matter. It was senior year and soon I’d be out. Or at least that’s what I thought.

I caught glances from the r******s in the park. They’d flirt with me but it was harmless. Except one who was kind of creepy and would make me an offer when no one was around. Nothing too bad. He just wanted to see my tits and feel them up and have me jerk him off. We’d go into his shed and I’d let him see and play with my tits, suck on them a little, then I’d undo his jeans and reach in and jerk him off in his boxers. I’d be lying if seeing his face as he was orgasming and then feeling his load cover my hand wasn’t a turn on.

It wasn’t long before he had me give him head. It was the first time I did it so he instructed me. For this he was sitting down and I took to it. It was the first time I saw it as when I jerked him off I never took it out of his pants, just reached in and did it. I could tell he was a bit on the thicker side but that was it. Once it was in my face I could say it was definitely thick and then some. I did my best with it. When he came he held the back of my head but made me keep eye contact as he pumped into my mouth. Seeing the pleasure on his face as his throbbing cock spilled his seed into my mouth that without thinking I swallowed down really turned me on.

Soon I was basically his. He had a girlfriend but she didn’t live there and after a couple months when I finally gave in and let him fuck me, he ended it with her. He told me right after he finished. His cum was all over my stomach, my belly button was full of it, and up between my tits. He really let loose, but was always a big cummer. He was wiping his cock off on the inside of my thigh when he told me after he ended it with her I was to move in with him. He was 42, I was 18. It took him about a month but he kept having me on the side until she was gone. Then that week I moved in. My mom enjoyed her booze and stuff too much to care.

I was basically his sex toy for the next 3 years until I moved on. I’d like to say it ended amicably but I left him for another older guy who I’m still married to to this day. Me 44 and he 67. In the end I made it out of the trailer park.

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# 76604 - by Tanya / February 4, 2025
- When I Was A Kid -
Straight Female / 37

The Third Child And The First Born Studying Biology

I was raised in a standard traditional household. Dad worked, Mom stayed home. We are four girls and brother. Our brother the first born. The four girls shared a room, two sets of bunkbeds, and my brother had his own room with the on suite bathroom. The walk down the hall to the bathroom, at any hour of the night, or to take a shower, meant that we weren't always properly covered. My brother liked to watch us, I mean on the toilet, in the shower, pull our skirts up, pull our pants down, pull our tops off, hold us down on the floor, spread our legs apart. You got it?

But that was life and he got to do what he wanted because he was the boy in the house and we were merely sisters. It was me that he decided to study biology with. He wrestled me until he was on top of me, and pushed my pants down, and got his penis in my butt crack, before sliding it down between my legs and right up my vagina. My vagina was wet and moist and warm for him putting his penis in and 'once fucked' I relaxed to enjoy it. I did enjoy it, sorry if you think that's nasty.

I WANTED him to do it again, over and over. I sucked his penis, got naked, lay on his bed for him to open my legs and inspect me. He liked my tits when I rode down on him, he played with them while I went up and down on him. I liked his penis in me, his hands on my tits or bottom. I snuck out of bed and went to his room to sleep with him. My sisters said nothing, my mother downstairs oblivious. The only thing she noticed was me being extra nice to him.

I suppose nature knows what it is doing, I was fourteen at the time and he was seventeen, and in spite of all the penis in my vagina and his orgasms, I never got pregnant. Mind you, we never tried to stop it, we just had sex whenever it was convenient.

We are all older, some of us married and divorced with children. My brother lives on the East Coast and I see him every now and then. But when I do, I remind him, it was my pussy he practiced in. It was my lips that drained his balls. It was my tits that he played with. He owes me big time, I made a man out of him.

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# 76590 - by Elizabeth / February 4, 2025
- True Sex Confessions -
Bi-Sexual Female / 50

When It Happened I Never Thought That She Would Become My Mistress

My husband got hot for one of the girls in his office. She was a girl who had never lived with a father, the father was in jail for manslaughter. My husband took her under his wing, and helped her finish college. Along the way he kissed her, once to often, and ended up between her legs and she thought she was going to be pregnant. She was 21, to his 44. At that time I was still dealing with my two, who were in grade school and junior high. As a stay at home mother, I was caught in that I couldn't leave him. But secretly I wanted him to have sex with her, to kiss her, and try to get her pregnant. I liked watching him as he put the move on her.

We went out to a New Year's party at the Hyatt that December when she graduated. We invited her to join us. She talked to me and I talked to her and I told her that I knew what she and my husband were doing. I didn't mind, but she needed to be nice to him and not embarrass him by getting with another guy. I also told her that we, the three of us, were staying at the hotel that night and we were going to learn to make love together.

I had never kissed a girl, much less kiss her pussy. She was a little more than comfortable with it and she let me kiss her up into an orgasm. We laid on the bed together and let my husband poke around trying to get into trouble. He finally took matters into his own hands and pulled me up into a kneeling position and he finished in me. We laid around in a tight three person pretzel. His hands went all over her and my hands went all over her. It was the first time I had been able to play with another woman's breasts, and the first time I got to finger another woman. She let me kiss her and she let him kiss her. By the time we got to sleep, to really sleep it was after seven in the morning.

With our New Year's party get together we had many more at our house. For long weekends, or when we went to the lake, or when we just wanted to feel her between us, she came to spend the night with us. When my son was going to graduate and go off to college we talked about her doing what women do, and that was get pregnant. She wasn't against it, she was turning 27. We celebrated by making love together and I was with her when she conceived her first one.

She is 37 now and had three children, and my two are out of college. I do the babysitting and after school care and do the errands while she works full time with my husband. We have a great big king bed so the three of us fit on it easily. She and I make love often, even when all it is is kissing and touching. I love to kiss with her and hold her tight against me. My husband is sixty, but he still gets it hard and likes to play with us, her mostly. I don't mind, really I don't. I would rather make love with her and as for him having sex with her, it makes me horny being there. She and I usually have a complete, meaning reaching orgasms, sex party after he turns over.

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# 76085 - by Gail / January 16, 2025
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