Painkillr

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Gender: Straight Male
Age: 55
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Profile Visits : 331
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I was 16 and my 14, for almost 3 years I lived with my cousins, we slept on the sofas in the living room. We would smoke a joint he would get horny, didn't think I knew he was hard, eventually he would fall asleep. I would creep over to his sofa and slowly and gently slide my hand under the covers.

He slept in just boxers. Once my hand got close, it felt really warm, I used my finger tips to touch, feel his semi hard penis, I would squeeze it on the sides to feel his thickness and stiffness. One time, I was lucky, he was out cold, and I opened his boxers and pulled it out. I was able to reach in and cup his balls and bring them out too. My heart was racing and his dick never been harder. Sitting there beside the sofa looking at my cousins beautiful cut thick cock.

Worked up the courage and licked his penis then backed off. He didn't make a move, so I went back down, picked up his penis and licked and then sucked it, first dick ever, it felt odd but so amazing in my mouth. My tongue all over his shaft and head. I just felt his dick getting bigger in my mouth. Was nervous but so into it couldn't stop myself. I kept sucking, this would be his first time, no one ever touched his dick before. It didn't take long for him to be fully erect and unloaded in my mouth. It was a lot of cum, some leaked out but swallowed almost all and licked up the rest. When he was cumming it was clear to both of us what was going on.

He made me suck his dick every day, a few times, he was young and horny. As we got more comfortable with this he would dominate me and fuck my mouth. For almost 3 years he never had to jerk off, he would just look at me and we would find a spot. He has a pretty large dick, long, thick, cut, nice head. Best sexual time of my life.

Who said "You can't have your cake and eat it". Well they were fucking wrong.
When I met my wife Jayne, her daughter Amy was only thirteen, but already a good looking girl. I knew she resented me at first, but after a while I could tell she was softening with her resentment. Then during a very boring Sunday afternoon with her mother taking a nap, Amy walked over to me and asked me if her mother and I still fucked. I was stunned to hear her say it, but answered her as best I could. I told her it wasn't any where near as often as we used to or as often as I liked. Her response was to tell me she knew, because she said, she always listened next door to us having sex. Asking Amy why she wanted to know, she told me she had her first sexual experience losing her virginity, and it was terrible.
Amy was fifteen at the time, almost sixteen. And even though I kind of knew what she was getting at, nothing happened for another year or so.
Again with Amy's mom asleep, but this time at night, Amy came in from where ever she'd been, went to her bedroom and then walked into our lounge totally naked. Amy was seventeen then, extremely pretty with a stunning body, great tits and an ass that absolutely deserved to be fucked. There was no misconception as to why she was stood in front of me naked, as my step daughter simply said "Fuck me".
Laying her down on the couch, I opened her legs and stared at the most gorgeous pussy I've ever had the privilege to bury my face into. I'm not kidding I must have spent half an hour licking and sucking away on her pussy and clit, making her orgasm three times. By then my cock was ragingly hard in my comfy shorts, so removing them I knelt up and let Amy see what was about to enter her pussy. The smile on her face boosted my ego, as did her comment "I just knew you were big". I'm not the largest cocked man out there, but at eight and three quarter inches, with a large bulbous mushroom shaped cock head, being fairly thick too, I'm more than capable of matching most guys.
The first time my cock slid into my step daughters pussy, she and I both sighed a huge exclamation of sexual relief. Without wanting to sound all creepy, I'd longed to fuck her and often caught her semi naked or naked in and around her bedroom and bathroom. I know now she was showing me her beautiful body on purpose, but at the time I had to make sure any given glances were from me only unintentional.
Each thrust into her body was amazing. Amy only helped all the more with her soft whimpering as I built up a rhythm, fucking her in long steady thrusts. Grinding my cock into her faster and deeper, she arched her back upwards and came on my cock. Shuddering for some time, she looked up at me and told me it was the first time she'd orgasmed without having to play with herself. It gave me more impetus to carry on fucking her, so I slid out, sat down and got her to sit on my dick. Watching her amazing tits bounce up and down as she fucked me, had my cock bursting to let go, but I wanted to last longer. Holding off, I let her fuck me as she wished and Amy took full advantage.
Amy's mom when we were fucking a lot, was a minx. A real horny bitch who loved taking control. Amy is just as passionate in having her own way, if not more so. So I watched the seventeen year old fuck herself using my cock to do it. And believe me it was one of the most beautiful sights I've ever seen.
Amy after some time, stayed on my cock, but turned around facing away. I could only see her back and her gorgeous tight ass from where I was, so I didn't see my wife enter the room. Amy did, but then Amy knew she'd be there. Still fucking me, sliding all the way down my full length, she asked me to help her along. Holding her ass cheeks, she pulled them apart, so I wet my middle finger and eased it up her ass. Crying out how wonderful it felt, I began to finger fuck her tight hole and buck upwards with my hips, forcing my cock deeper into her pretty pink pussy. Fucking each other quicker and with more urgency, Amy climaxed again, only seconds before I could hold off no longer, my cock exploding deep inside her pussy.
Amy sat al the way down onto my cock, then leaned back. It was then I saw Amy's mom watching us and playing with herself as she stood in the doorway. I was about to frk when she put her index finger to her lips and shushed me. Walking over, she gently kissed Amy on the mouth, the leaned over more and kissed me too. Moving to our left, she sat down and moved her panties to one side. As Amy and I watched, my wife frigged her clit and eventually made herself cum.
I was totally stunned, and really didn't know what to say. Thankfully it was my wife who spoke. She told me Amy had gotten undressed in our bedroom as they spoke about her fucking me. It turns out they'd been speaking about Amy experiencing what it was like to be fucked properly. I obviously wasn't her dad and her mom figured I'd seek out other women if she wasn't capable of keeping me sexually happy. Killing two birds with one cock, is what she called it.
We all showered one after another that night, but instead of retiring to my own room with my wife, she asked me to stay in Amy's room. Throughout the night myself and Amy had sex and quite a lot of it oral. By the time the sun was rising, I was knackered, but had enough in me to tongue out my tep daughters pussy and asshole one more time. Once Amy was suitably wet from my tonguing, she backed onto my cock as we spooned. Guiding my cock to her asshole, I slowly and carefully entered her rear hole. I took my time making sure she was okay with the size of my dick sliding up her asshole, but I needn't have worried too much as Amy's asshole took every inch of my cock. Holding her tits in my hands and kissing her neck, I fucked my gorgeous step daughters asshole until we both orgasmed. It was and still is one of my most memorable fucks, as we slowly moved in tandem with one another.
We were both asleep when her mother entered the bedroom. My wife woke me up and we left Amy to sleep. Downstairs sat at the kitchen table we spoke for over an hour before Amy rose, about why she'd wanted Amy to seduce me, and what she wanted from an arrangement which still exists today.
My wife is truly a remarkable woman. She knew her libido was dropping, yet she also knew of her daughters lust for me. It to her wasn't a big deal to share me with Amy, and even though at the initial part of all this, I was a bit at a loss as to where it all may lead, I now know both women love me in there own way. My wife and I love each other deeply, where as Amy and I have a sexual love. It's pure unadulterated lust both ways and one that now occasionally includes my wife.
Amy is now nineteen, twenty in two weeks time. She told me yesterday as I was slowly fucking her mother on the bed next to her, that she thinks I should marry them both. Her mother my wifre smiled at her daughter, gripped my ass cheeks and pulled me deeper into her hot wet pussy.

I moved away to college for my freshman year. My little sister came up for a football game and she stayed with me in my dorm room. With my sister in town my dorm mate went to stay with a friend in an apartment. A senior had invited me to the game and he got another ticket for my sister. After the game we went out to eat, and we then went to a party. I told my little sister to stay close to me, not to go off on her own. It wasn't an unknown boy who got ahold of her, it was my date. He gave her beer, and he fondled her up completely, he took her boob out of her shirt and sucked on it on the couch in front of God knows who. He had his hand deep inside her pants, she was completely ready to get screwed. I stood in front of them, and he got her on her back on the couch and screwed her. No one paid any attention, they looked and moved on, no one noticed how old my sister was, a couple of girls stood by and complained that they weren't getting any.

After he finished with my sister, I took her to the bathroom to clean her up. More than anything I wanted to know when she had her last period. She had barely turned 15 when she had her baby. He paid me and I pretended to give her money for the baby. To keep him in line I had to give myself to him. He never stopped wanting my sister, and she was always ready for when he wanted her. She was on the pill after she gave birth, but still, baby sitting my nephew while my boyfriend was screwing my sister just seemed wrong. I kept a playpen in my apartment for the baby to sleep in when she came to stay with me. He would hug me, maybe make love to me a little, and then turn his attention on her and make love with her like he was never going to see her again.

My sister was my maid of honor when I got married, she was 17. My nephew was in my mother's arms, my mother never realizing she was watching the father getting married to the sister. On my wedding night, my sister came by to get herself taken care of before we left on our honeymoon. During my entire honeymoon my husband lamented that my sister was not there with us.

Because she is a single mother she doesn't date. The truth is she doesn't date because she is already in a relationship. She struggles on her income. The truth is that my husband and I give her a substantial amount of money every month. She can't go to school because she is a single mother. The truth is that we have offered to support her if she will go to school. She wants to have another baby, as my nephew is five. I have drawn the line, but she slips under the line and my husband won't enforce the rules. She is his baby girl and she has him wrapped around her finger.

We were trying to have a baby, she did not get pregnant after six months trying. Exam found cancerous tumors that rendered her childless after the surgery. They took a lot out of her and she changed. We argued all the time and it got the point I no longer wanted to live this way.
We had counseling, said sexual tensions were a problem, but the largest problem was her issues of never being the mom she wants to be. We had sex after the surgery and it was not bad, but it was no where near the same as before.
She came to me with a fix for this. She would find another woman to join our relationship. She would have a baby the three of us could raise. She would have sex with me, but I could freely have sex with either and both women. Or in other words another wife. (We are not religious at all)
I agreed to the arrangement if she could find that person. I would want to wait a while before having a baby in this until we knew it would work.

She brought in her cousin. Her cousin is ten years younger and was beaten by a gang at her school. She's a home type person who builds web sites. She makes good money and works from home. She's a normal girl with emotional issues from the beating, but she's doing much better now. She lived with us for three months before we did anything sexually. My wife stayed with a family member for three weeks leaving her cousin and I alone. My wife's family is understanding of the arrangement, her aunt is ok with her daughter in this arrangement. She worried her daughter would never have a life or romance, she would hardly leave her bedroom.

She was a virgin but not a bleeding virgin, she was a very sexual girl who used fingers and sex toys. I had no problems penetrating her and she never used birth control in her life. I took the chance it would not be easy for her to get pregnant, I would take the risk. We had out honeymoon for those weeks when we had sex every night and ever morning. Her period did not bother or stop her from wanting sex. She loved it, I loved giving it to her. I will confess here, but would not to anyone else, She's much better feel up inside than my wife ever was. She's a lot hotter toward sex to the point it's her favorite thing to do.

The weekend my wife came home there was some confusion who would sleep where. We tore out the wall between two rooms and created a new master bedroom. California king bed and two bathrooms were added. A large walk in shower with tower and rain type shower head system. We could all sleep together we could all shower together. Until that was finished we slept in a queen bed together. My wife encouraged her cousin and I to have sex, She supports that an it would be beautiful to watch and be part of it. While we had sex my wife kissed me, would massage her cousin's body breast and kiss her back softly.

One night after dinner we went to bed early and my wife decided to join us. She preformed oral sex on her cousin after she and I had finished having sex. My wife gave me oral sex to get me hard and then took her turn having her sex with me. The next morning her cousin told me that was uncomfortable, It's not something she wants again. I told my wife, then she started crying. She wants to be part of this. she told me that she held my nuts while I came in her cousin, she could feel me shooting in her, it bothered her that it was not her taking that.

It's become a strange house hold, Her cousin's fallen in love with me and I her. While I still love my wife It's a strange feeling after years of arguing and dealing with her emotional issues post cancer. My wife's got a job offer that would make her work midnight to eight am. Meaning she would sleep alone in the day time. My lawyer said it's probably smart we fly to a quick divorce state or country and I marry her cousin, before we have a child. If not it could get ugly later on should my wife want an ugly divorce. I told my wife, she's ask if I could marry both women. She will buy air tickets to Barbados where I can marry both of them.

This is crazy, this is nuts and this is not where I want to inject a child right now

Off on a three day trip tomorrow, and I simply cannot wait. My husband will be staying at home (work) so I'll be taking Jack his seventeen year old nephew for company. Which was in a roundabout way my husband's suggestion.
What my husband doesn't know, is for the past two months, Jack and I have been having sex whenever and wherever we can. Our first sexual engagement was in my car. I'd driven over to my sister in laws to give Jack his seventeenth birthday present, but all hell was breaking loose at their home (Families eh) Driving Jack over to a place I know he likes to chill out at, I couldn't help but notice his cock bulge. Jack was uncomfortable and I could tell. Asking him if things were ok, he told me he'd not had sex yet and all his mates had. Before I could say anything in response, he added "It's because I only want you".
Now I'm not going to lie and say I hadn't noticed, because I had. What I will say is I wasn't expecting what happened next. Jack undid his shorts in front of me, lowered them and out slapped his extremely thick cock. It's not overly long at six and half inches, but it's so utterly and gorgeously thick. I'm no prude, but I was shocked at what he did. He saw my face and started to apologise. But by then I was horny myself staring at his growing cock. Putting both hands around it, I began to masturbate my husband's nephew.
Jack groaned and began to kind of fuck my hands, yet I wanted to do something else for him. Shuffling around, I maneuvered myself so I could lean over. Still holding his now fully erect cock, I leant over and sucked in the thickest cock ever.
It was supposed to be a one time event. I was only going to blow Jack and let him feel special for those brief but exciting moments, but things didn't turn out that way. Jack was taking an eternity to cum. Even though I was tossing him off and sucking hard and deep down my throat, he just wasn't cumming. I myself was incredibly turned on, so not caring if anyone might have seen us, I removed my skirt and knickers, moved us around a little, and mounted his amazingly fat cock.
I felt my pussy spread like never before, and I swear before his cock fully bottomed out up my pussy, I was already having my first climax.
Throughout our first fuck, Jacks face was pure lust and surprise. It was never my intention that day to have sex with Jack, although in one of my more sexually wicked moments weeks earlier, I had envisioned him tonguing out my pussy. Anyway that's something else.
His cock felt perfect for me, so thick and so very hard, that once I really began to fuck Jack, I placed his hands on my breasts, leaned into him and we began to kiss. Taking every inch of his cock, I soon felt him shuddering beneath me and knew he was about to cum. I was right, but before his cock let go, I had a second orgasm which nearly blew my head off. It was so intense, so powerful throughout my entire body, I collapsed on top of him, which in turn had Jack pumping his cock deep inside me, filling my quivering pussy with his seed.
Separating, I held his hands and then moved them to my pussy. His cum was leaking out, but I wanted him to know something. Making him scoop up his cum, I put his fingers to my mouth and licked every drop off. Swallowing his cum, I told Jack "Anytime you want sex from now on, text me".
The very next day as I was having my lunch at work, Jack text me to tell me he was horny. Before I drove home after work, I had Jacks cock fucking me from behind again in my car. Again I orgasmed so hard, I was shaking like a leaf, and I knew then we'd carry on having sex.
The trip was supposed to be with my husband, but his business needs him, so he suggested I take someone else. I mentioned a couple of my girlfriends, but also added in Jacks name. My husband said it would be good for Jack to out of his families environment for a while, so I arranged it so Jack and would take the trip. Telling my husband sleeping obviously would be in separate rooms at the cottage, I and Jack know full well we'll be sharing the same bed.
Over the past couple of months, Jack and I have had sex most weeks, at least twice a week, sometimes a lot more, depending on time and circumstances. Yet we haven't had a chance to have prolonged time together overnight. I've taught Jack a lot, but over the next three days I'm going to have him learning a while lot more, and I can't wait to have him and his wonderful cock all to myself trying different things to pleasure us both.

The Saturday I'll Never Forget

I was 14 that summer and supposed to be grounded that week. Mom and dad both worked on Saturday's. Mom told my older sister try to keep an eye on me. And not let me find any trouble. Well my Sister Kate was 18 and had thoughts of her own. Which I learned later on. Later that morning Kate asked you wanna go to a BBQ that my coworker friend is having? Me ? Sure thing anything from not being in the house all day. We took the spare VW Bug. Upon arriving I meant a few coworker friends. One was Billy Jo teased my sister oh you brought me a date. My sister responded with settle down he's only 14. Then smiled at me. Had to 50 to 60 people there. Couple hours later Kate couldn't be found. But her car was still here. The food was smelling pretty good. Nothing better BBQ hamburger. Sitting at a picnic table Billy Jo sat down next to me. And said Sister said your 14 . I replied yep. She said she's 19 and remembers being 14 once. Few minutes later she said lets go check this house out. Well it was much larger than ours. So I replied ok. We ended up on the second floor and checking out the bedrooms. After we entered she closed the door. Then asked wanna know what I've doing when I was 14? I replied sure. She leaned down and kissed me and said giving up my pussy. She said lets fuck. I had my first fuck that afternoon. And not knowing the whole deal. She helped me mount her slide my dick inside her. And moaned oh my your still hard after releasing. Lets do it again. The second time seemed little longer than the first. She had this funny look on her face and she was saying yes and don't stop. During this time she was rubbing both of her titties and sliding her hand down between her legs. She knew something I didn't she said thrust harder. My dick was feeling funny then my whole body started shaking. I then collapsed on top of her. She held me tight . Said it will be ok. Took some years What I learned that she used me for a toy boy fuck. But it was great.

Exhibitionist Teacher

When I was a senior in high school, my English teacher was Ms. Longo. She late 30s, blonde, cute, nice body, always wore loose bohemian type clothing and rarely a bra. This was the late 70s and times were different.

Ms. Longo liked to hold class discussions sitting on a desk near the front, sitting on the desk table part, feet in the seat. She always wore dresses, knee length or longer. As she held discussions, her knees and legs would drift slowly apart. Before long, every student was able to look up her dress at her white panties. Now I’m sure I don’t have to explain that every 17 and 18 year old boy had a raging hardon when this happened. Ms. Longo would focus on the boys and ask direct questions about the material we had read, all while opening her legs knowing the boy she was speaking to was either staring at her crotch, or wanted to.

I remember one time she had us discussing the lyrics and meaning behind the Beatles song Norwegian Wood, where a guy meets a woman and sleeps in her bathtub. Ms. Longo asked very pointed questions about whether they had sex, if so did they do it in the bathtub, or was he was he full of sexual tension but didn’t get off? She took pleasure in embarrassing people about sexual matters. Especially the boys but girls too.

Another time she put on a show except this time she only flashed up her skirt for a split second at a time. That was because she was not wearing panties that time. It was the big topic of discussion around school the rest of the day. Lots of guys hit the bathroom after her class to get off. Honestly how she never got in any trouble I don’t know.

Not surprisingly about a year later (I had graduated) one of the senior boys saw Ms. Longo coming out of a hotel in Boston holding hands with a classmate….a boy quite shy and innocent actually. So I guess Ms. Longo had her own sexual tension and need. I occasionally still jerk off to the memory of Ms. Longo behaving like a slut…nice memory, some 46 years later.

Family Gatherings At My Uncle's

i have a big family, literally related to like 1 in 30 people in our little i****d county, and we would have a family get-together every holiday.

the 4th of July, Independence Day for the USA, is when my uncle, "Little Girl", would host the gathering. since i relented my virginity on my birthday, he decided it was open season on me. He's a professional fisherman and charter skipper, a hard weathered man that is home on the sea and works hard every day.

the guest apartment is above the detached garage on the back of his lot. it's used to let charters from out of town stay the night and head out for a day of fishing early the next day. i became well acquainted with it after my birthday that year.

he lead me out to the guest apartment, i knew what i was there for. he had my top and training bra off in moments. his rough hands felt so good on my preadolescent perky breasts, this time he was much rougher.

he'd been drinking. he picked me up and literally threw me onto the bed. i opened my cutoff shorts, and slide them off while he watched. he was on me a moment later. he pulled his cock out of his pants and shoved it into me. i was so wet with anticipating him, that i it slide right in. he pounded me so hard that my little butt was bouncing off the bed, then quiet. he strained and grunted, and i felt his cum fill me again.

he rolled me over and pulled me back to my knees and rammed into me again. he started calling me his "little bitch pup" and grabbed my butt checks and squeezed hard. his hands are so rough and strong, it felt like he was trying to pinch them in half! he slapped my ass, and started pounding me even harder! i remember orgasming--i literally squealed, when i did. a short time later he shot his cum into me again.

he pulled me up to kiss him, then pushed my head down to her crotch, and forced his cum covered cock into my mouth. he stroked my hair and told me, "Good little bitch pup!" over and over as he stroked my hair, and i cleaned and sucked his cock.

this is pretty much my 4th of July celebration with my family, even today.

Janna

Sharing Is Caring

My biological father is a self centered ass hole who mistreated and left my mom for another woman. For a while me and my sister took care of her while she got her mental health ready. She had us very young and all three of us could pass for sisters. Right before COVID she found herself a good man who she started dating. He was a complete fit hunk, with a muscular dad bod and super sweet. He was always patient with my mom and that made us like him even more. When I hit puberty I was a complete mess with boys but he never once mistreated me. During COVID he started living with all three of us and would take my mom to work. I caught my older sister multiple times cuddling with him and I started having a crush on him and getting jealous. one morning I couldn’t help it but I was wet and super horny and gave him head on the couch. He backed off after he came in my mouth and didn’t talk to me until my mother came home. We had a talk with everyone that night and my mother actually was not mad at us or him. She mentioned it was okay since we were older now and didn’t mind as long as we wanted it. She put me on birth control and ever since he’s been fucking me and my sister at home. He is an animal and his cock is so big. I couldn’t take him at first but after a few times got used to him after riding him. My older sister recently went to college but comes back on the weekends. I can tell because I’ll here loud movements and deep moaning. When my mom gets home from work he never leaves her side and we respect that.

Mom’s Half Sister

My mom’s half sister (28) was with us for three weeks. She has been living in Germany, is very beautiful so much so that I can’t keep my eyes off her. My mother has scolded me now several times for staring at her but it can’t be helped. She, my aunt, the first week gave me a big hug said I was adorable and kissed me long on my lips. I was rock hard immediately! Fuck, I did not expect that and went into the shower to stroke one off. She asked me if I ever use the sauna we have downstairs which I don’t. None of us do. I told her it’s too hot. She said only because I don’t know how to do a sauna. “You must be nude.” We never use it but she’s been using it everyday. There’s a small window in the door and I have been tempted to peek but don’t want to be caught. So last weekend mom went to the next town over to visit a dying friend. My aunt wrapped in a short towel passed by me and said, “Tom are you going to join me for a sauna?” Fuck yes! I went to my room, stripped down and put a towel around myself. My cock was rock hard and obvious. She giggled when I entered, “You are excited about a sauna?” I could not believe how stunning she is. Her body naked is better than what I imagined. She said, “Take off your towel and place it on the bench to sit upon.” I did but I felt embarrassed with my six inch pistol sticking straight in the air. She complimented me on my erection. “Very tempting” she said. I wish!!!

We talked for twenty minutes but with her hairy pussy exposed and those great tits my cock never went soft. She commented on that as well. She stood up, walked towards and in front of me, placed my hands on her tits and her hand on my cock. I fucking ejaculated on her tummy and pussy hair immediately. So embarrassing. She laughed and said you're just sixteen, lets get it hard again. With that she led me out of the sauna and to her room. What a great day. She taught me how to eat a woman’s pussy, feel and suck on her tits and do all the things a young dude needs to know to satisfy a woman. She kissed and sucked on my cock and balls and I loved her scent of her pussy all over my face. I didn’t want to wash her off me. With only a few days left before she went back to Europe I asked her if we were going to make love again before she goes. “Let’s hope” is all she said. Mom was always around so opportunities were fading. I made sure to bump into her when she left the sauna wrapped in a towel. She let the towel drop, gave me a deep kiss, put her fingers into her pussy and then put her fingers into my mouth. The smell was awesome. That was as close as we got to being together before she left. The night she departed, when I went to bed, a pair of her panties were under my pillow. I just laid there smelling them while jacking off. What a woman. I can’t stop thinking about her and feel like I’m in love. It’s killing me.