Straight Male / 29

I am a 29 year old married straight man who loves dressing in womens clothing and being fucked in the ass with a strapon.

Twice a month my wife helps me wax all of my body hair, dresses me in lingerie of her choice, locks my cock and balls in a cage that prevents me from getting an erection and has a thick rod that pushes into and stretches my urethra. I am then requited to eat her pussy until she's satisfied, 6-10 orgasms, before she lubes up her 8 inch long thick strapon and forcefully penetrates and fucks my ass raw. Bent over the couch, crouching on all 4s on the ottoman, laying on my back on the gyno exam table I am left a quivering mess when she's done using my asshole.

I really enjoy both the pain and the pleasure of having my asshole so thoroughly used, the pain and pleasure of having my cock abused and the thrill of being dressed in womens clothes as it all happens.

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# 27989 - by Anonymous / July 23, 2016

- Fetishes and Kinky Sex -

Straight Male / 50

Lily and Tom were neighbors for many years, they were right there when my wife Joan passed away. We were like peas and carrots the four of us always doing something together even if going out to eat.

After Joan was gone I wasn't much into being the third wheel with Lily and Tom, mainly stay at home going out only when I had to. After a long while of mourning Joan I tried to move on with my life.

Lily tried to hook me up with a friend or two but I just wasn't into it. At some point I began to think about sex. Joan and I had a great sex life, she had a great collection of heels and bedroom outfits to wear for me. The idea of going to bed with a woman naked just never appealed to me no matter how horny I was. At some point I had to express that to Lily because she asked me why I didn't want to start dating someone else. I even told Lily that I couldn't bring myself to get rid of Joan's things, especially all of her heels and sexy night wear.

At some point Lily would come over to check on me and always the conversation turned to the things I told Lily about before. Frankly I was a bit embarrassed to tell that to her, I just didn't know she would keep bringing it up almost every time. It was like she was picking my brain for answers on why I liked those things so much? Finally I had to tell Lily one day not to bring it up anymore, it was embarrassing and a bit painful.

Lily reached into her purse and pulled out her phone and handed it to me. At first I wasn't sure who or what I was looking at. It was a picture of Tom and he was dressed up in women's clothing. Lily had taken a picture of Tom standing with a glass of wine in his hand. Tom was wearing a frilly white blouse, black skirt, stockings and heels. Tom was also wearing a dark semi curly wig and makeup. There was another picture of Lily and Tom seated on the Sofa with a glass of wine in their hands. Lily was wearing a rather skimpy bodysuit with stockings and heels, her breasts easily noticeable through the thin nylon material. All the years I we had known Tom and Lily I would have never suspected this from them. Hell I was shocked to see Lily wearing such high heels, she always wore flats or very low heels.

I just looked at Lily and then back to the picture on the phone until the screen went dark. I didn't know what to say to that. Lily took the phone and dropped it in her purse and asked me for a cup of coffee. For the next hour Lily laid it all out. Tom had been a cross dresser for years, she never dared tell anyone about it, not even her Mom when she was still alive.

Lily told me about a strapon she used on Tom, she would have sex with Tom dressed as a woman. I wanted to tell Lily I had heard enough but honestly I couldn't bring myself to, suddenly I wanted to know everything about what they did. I was shocked and for some reason excited that Lily would share this with me.

I asked Lily about Tom doing her? Lily said Tom didn't perform, his cock was in chastity all the time. I actually had to ask what she meant. Tom wore a metal cage around his cock, never to get hard and even peed through it daily. I couldn't help but ask Lily how she got hers so to speak. Tom would orally do her and use his fingers, that was about it. Lily went on to say they hadn't had normal sex in over Ten years. I think Lily realized she had told me things she didn't plan to, she got up quickly and left. I watched as she crossed the street to her house quickly, only looking back at my house before going inside her front door.

I didn't see much of Lily after that day, I'm sure she must have been embarrassed after sharing her secrets. For her being 50yo Lily was still attractive, obviously she didn't have the figure of a Twenty year old but she was still in pretty nice shape being on the petite side.

One night I was watching TV when the doorbell rang, it was almost 8pm and there wasn't many people out now during the work week. I answered the door to see Lily standing there all made up as if she were going out on the town. In fact Lily was over dressed wherever she was going to go. She wore a lot more makeup and her attire was rather on the alluring side. It didn't take me long to notice she was wearing high heels as well, the ones I had seen in the picture

I invited Lily in and she seemed to hesitate for a moment before stepping inside. We sat in the living room and I could see that Lily was nervous about something. I had the feeling that Lily was about two seconds from crying. I sat down next to her and asked what was the matter?

Lily looked at me for a moment and then kissed me dead on the lips. It was like a sudden shock to feel the softness of a woman's lips on mine once again, it had been almost two years since I had felt Joan's mouth on mine.

Lily and I made out like two kids in heat and soon I felt the stirring between my legs almost at once. My hands found the curves of Lily's breasts through the thin material of her blouse and I squeezed them gently. Lily made a sound that let me know it was okay and not to stop.

But suddenly my senses came back, Lily was married and should I be doing this with anyone this soon after Joan? I think Lily sensed what I was thinking and she pressed her body to mine so I wouldn't pull away from her.

We never made it off the sofa, we made love right there. I took Lily with her still mostly dressed except for her blouse, bra and panties removed. I went down on Lilly, pushing up her black skirt and feasted on her wetness. Lily dug those heels into my back the way the Joan used to do when I made her cum with my mouth. My cock throbbed underneath and I wanted to be inside of Lily now more than anything.

I broke the moment, telling Lily I had no Condoms. She suddenly looked up at me and said I didn't need one with her, it was almost as if she would have been disappointed if I had used a Condom with her. I tried to hold back, tried to make it last with her but I couldn't. It had been almost two years and I was desperate to have that feeling of release again. I came and the sensation of cumming was overwhelming.

I know I must have sounded like a wounded animal when I came. Lily's eyes were closed, she was cumming in her own way. Her nails dug into my back as I pumped my juices inside of her, I could feel her contractions around my hard cock as she climaxed.

Finally it was over, I lay partially on top of Lily. Her small breasts with her nipples hard as buttons. I wanted to savor them again and Lily allowed me to do so. My spent cock slipped out of her soon after and I struggled for the energy to get up off the sofa. I told Lily to use the guest bathroom I would go upstairs to use the other to clean up.

When I returned a short time later Lily was nowhere to be seen, the bathroom was empty and Lily was gone. I spent the rest of the evening looking over at her house, I wanted to call to make sure Lily was ok. Finally around midnight I went to bed, it was the best sleep I had in a very long time.

The following evening Lily was at my door again, she was dressed as she usual in flats and regular clothing. She started by saying not to be mad but she had to get home to Tom. Then she told me other things after we sat down.

The reason she had to get home was the ..(continue confession)

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# 28688 - by Anonymous / September 28, 2016

- Anything Goes -

Bi-Sexual Female / 51

My Husbands Ass Is Mine

I regularly fuck my husband up his asshole. I love to do it, I love to make him sub to me, and be the one who "gets fucked" in our relationship. For years I let him do anything he wanted, knocking me up because he wanted to see me grow a big belly and wanted to suck my milk. I stayed full of milk for almost 2 years after each of our two kids just so he could nurse on me and empty me twice a day. I was experienced, more so than he when we met, so I let him sew his oats with me. I let him get it in all my holes, anytime he wanted, including the college trip to the islands and the nude resort where I let him fuck me in front of everyone, even in my ass. I had experienced a live in situation with two women, one in college and one after and I was the dominant one in those relationships.

So after he was banging his secretary and I played the video back for him, he didn't want to lose everything in a divorce, so he's now my bitch, anyway I want it. I still ride his cock and get off, and let him get off every week or so. But I now stretch his ass with a 2" thick, 10 inch long strapon. About 3 months ago he started shooting while getting fucked, no one even touching his cock. So he likes it now. With the kids gone and on their own in other cities, I not only crossdress him in lingerie I have nice blouses, bras, skirts and shoes that I make him wear.

Fuck him . . . literally.

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# 50486 - by Dm / March 28, 2021

- Anything Goes -

Straight Male / 20

Pegging By Older

There is a divorced woman that I have sex with. I met her and fucked her about 4 years ago, she was 37 then, now 41. She has a nice body, plump but really nice and firm, big tits that don't sag much and she has let me have sex in all ways possible. For the last year she has been pegging me, using a strapon dildo and fucking me in my ass. She started by letting me fuck her ass then reciprocating. It's very embarrassing sometimes if her friends are over, she shows them pictures and videos of me fucking her in various ways, even fucking her while wearing her lingerie, and now she shows me getting fucked. Lately she talks to me like she wants me to let her have a guy over who wants to fuck me. I don't want to do it, and if she insists, I don't know what I'll do. I may let him, I really don't want to stop fucking her, she's incredible. She's even let me fuck some of her friends, mostly older or fatties, but I fucked them anyway.

I know if she gets me to let a man fuck me she'll video and take pictures. I really don't want that.

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# 53053 - by Eo / August 16, 2021

- Fetishes and Kinky Sex -

Straight Male / 18

2 years ago I had my first sex with a much older woman I met on a nude beach. She was 63 and a widow, I am still fucking her and a lot of her friends, some older, some much older, others younger but very fat or not at all good looking. I've learned a lot and fucked a lot. She started refusing me pussy from her or anyone if I didn't let her fuck me. For over 18 months now I've been taking her strapon up my ass for 30 to 45 minutes a day while she calls me names and tells me what a whore I am. Sometimes she does it in front of her friends.

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# 44339 - by Anonymous / May 2, 2019

- Anything Goes -

Bi-Sexual Male / 21

Older Domme Made Me Bi

When I was 17 I met Gracie, she was a neighborhood wifey whose husband had left her for a younger girl. She was 37 at the time, I was a gawky 17 year old who wished he could get laid. After a few months I got my wish. I had learned a lot about Grace and her husband and all the sex they'd done. He was pretty kinky, loved to make her sub, even "rent" her to other men. She taught me well, taught me a lot and I loved the feeling of her mouth around my cock and she would always look at me, show me my big load in her mouth then swallow. That was always followed by a kiss, later she would always keep a little cum and push it into my mouth when we kissed. Her pussy was hairy when I first fucked her, I loved how it felt so warm and firm around my cock. Eventually she had me fucking her ass too.

After a while her cum kisses became with her mouth full of my cum and we shared it. To be honest I hated the taste, but it kept her happy and I wanted her mouth, her pussy and especially her tight ass to fuck. We hadn't buttfucked in a couple of months and I was really wanting it, but she asked why is it only her who has to take it up her ass. What she was leading to was using dildoes on me, in my ass first, THEN I could fuck her ass. She started with thin ones, then thicker, vibes, and eventually she came out with a strapon that was 10" long and 2" thick. She would use me for up to an hour that way before I got her butt. Eventually, I just didn't even think about it. I just let her do it. My now I was 18 almost 19 and was getting as much sex as I wanted, and all I had to do was let her fuck my ass. It became part of our normal sex routine.

Then she got more dominant, making demands, and I let her. I really didn't have any desire to dom her, but she did me. I guess she was making up for all the sub times for her ex. One day she brought up bringing another guy over that she fucked. I never even thought about her having another cock in her life. Turns out she had just started with him, he was up for coming over and watching us. She dommed me in front of him, made me wear a black babydoll nightie and he watched while she fucked me in my ass. She took it out of me, and moved up on my back holding me down and I could feel him between my legs. I felt his cock moving around my buttcrack and I said no, but she kept me pinned down. "Just go with it baby, do it for me". turns out he wasn't fucking her, he was gay and wanted to fuck me, he wanted to fuck a teenager.

He fucked me, shot in me, and she rolled over and dragged me on top of her. She said how much I must have liked it because I was so hard. I stuck it in her and came in minutes. After that the other guy sucked my cock clean of my cum and her pussy juice, then she sat on me and Iicked her clean. After a while she wanted me to let him fuck me again, and I sucked him hard, he laid me on my back and fucked me missionary for about 45 minutes before he came in me again. He got dressed and gave her $200.

That was almost 3 years ago, I still am with my domme, older woman Gracie. She hires me out to bay and bi men and most of the time watches as I get fucked or suck their cocks. I still get all I want from her, and have come to like bisex. Its so much different than her dildos, natural cocks feel much better. I went on a trip for a couple of weeks and I let 2 guys I met have sex with me. I'm definitely sub, and most definitely bi.

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# 49471 - by QP / February 6, 2021

- Fetishes and Kinky Sex -

Straight Male / 39

My Wife No One Knows

I have been married to my wife for 16 years now. I was 23, she 26 when we married. She still is very hot. She is stunningly beautiful, 5ft. 7in tall, 120lbs, C cups that sag a bit now, but are still really firm, with puffy, perfect nipples. She has a great shape, keeps working out and looks better in a bikini than she did when I met her.

She was very experienced at sex and relationships before me, I was not before her. I had made it with 2 girls, one was a drunken gangbang, the other lasted 2 years. I never really felt a bond with the longer term girlfriend, but I immediately felt something when I met the TA in a college class. We spent time together, mostly talking, drinking coffee during the day. Finally after a year, she said she had broken up with a boyfriend. She had a rough time with him I know, he was very dominant and she didn't like it. From her talk she wanted to be "in charge" of the next relationship. In talking with her I realized this didn't mean she would wear leather and carry a riding crop, but rather she had things she liked sexually and she wanted them often.

So, I asked her out and her response was "You mean like a date? A date type of date? " I replied affirmatively and and her excuse was that I wasn't really ready for someone like her. After 2 months of practically pleading and telling her I was ready and after all, it was "just a date" not sex. Her reply was "Not Yet". So fast forward, we had been dating and having incredible sex for a year. She let me inside her ass, which I had never experienced and loved that above anything. She would rub my prostate with her fingers when she blew me, she started with one, then her norm became three, sometimes four fingers. I did things for her, she loved to talk dirty, so did I, she made me shave my pubes, not hers, and wrote in permanent ink " Margie's Cock" just above my cock. She kept writing it every few days, so it would eventually take over a month to fade away. Other than sex, she was very womanly, very feminine, loved pretty clothes, flowers, she is an incredible cook, and all the "normal" thinking things about a woman or wife.

On our wedding day, no one knew but it was to be our first time having sex. Not conventional sex as we'd had that for over 2 years by that time. Under her beautiful wedding dress, she had a strapon cock, under my tux I had on a pair of white lace panties over a garter belt and stockings. I wore socks over the stockings below so no one could tell. On our wedding night I undressed her, I got undressed to my underwear. She handed me a bottle of lube from her purse and I lubed the strapon cock, then my ass. I laid on the bed on my belly, in my stockings and garter, but she told me to turnover. I got fucked missionary by my wife on our wedding night. It was the first time she got to fuck someone, and my first time getting it in my ass.

Since, it's been an incredible ride. I fuck her, she fucks me, I eat her she sucks me, we have gone on vacations to nudist and hedonist resorts and fucked in front of others, she made me have sex with two other women at one of them and with the one who spent the night with us she had lesbian sex. I have a perfect wife, and the most incredible, unconventional sex life with my very unconventional, beautiful, hot bodied wife.

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# 50552 - by Jus / April 1, 2021

- I Did It For The Money -

Straight Male / 18

The Old Woman

She's 71, weighs about 200lbs, and has super huge tits and a hairy pussy. She's paid me for sex for the last 2 years. I've only fucked her with my cock in her pussy about 10 times, sometimes it goes in her mouth and sometime up her tight butt. Mostly though, I have to dress in nylons, garter and a shorty nightie, all black. I already have pretty long hair, so I put on some eye makeup and lipstick. We kiss, then she feeds me her big tits, I suck on them for about 20 minutes or more, feeling her pussy. Then she pushes my head down and while I'm licking her clit and her pussy, finger fucking her she calls me Sharon. Then she cums, and when she recovers she leaves the bedroom. When she comes back she is wearing her strapon cock. I lube it, and have already lubed myself. I then get fucked in my ass till she cums again. Sometimes it's 5 minutes sometimes is up to an hour of having my ass pounded. I usually then lay there and she watches me used my hand till I cum all over myself. She licks it off me and sometimes feeds me a little on her finger.

I can then take off the makeup, get into my street clothes and when I come out of the bedroom and bathroom, she is waiting in her fat housedress with an envelope of cash for me. I do this twice a week sometimes more, and have for the last two years. Each time there is between $150 and $ 400 in the envelope depending on how many times she came or how long she pegged my ass.

it's money, that's all I can say. She was the first pussy, ass, and mouth I ever fucked.

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# 50853 - by Us / April 15, 2021

- True Sex Confessions -

Straight Female / 25

Cd Hub

I was married for 2 years before my husband finally came out and told me he is into crossdressing. Mainly lingerie and sexy undies, heels, and stockings, not always outerwear. I said he could do it with me if he was dressed once a week. That turned into 3 times very quickly, now as soon as it hits 9pm he leave the living room and comes back out dressed. He still fucks me and it's good, it's really good, one of the reasons I fell in love with him and agreed to marry him were his skills at sex. Sometimes though I don't get fucked, I get eaten and he fakes being a lesbian woman. I'm not crazy about it, but then he brought home a harness and dildo for me to use to fuck him. I told him there is no way he could take that thick a dildo up his ass for his first time. I still remember all it took for me to get used to anal sex.

His reply was that it would be alright. He took it, and it's a full 2 inches thick,9inches long. He took it in as I was trying to go slow. But he reached around with is legs and pulled the full length into his ass in one stroke. I went nice and slow when fucking him and he was begging for me to fuck him harder and faster. So I did it. Now we have an even bigger strapon and he takes it all rapid fire. I finally sat him down, and got him to be honest with me. He had been in gay relationships, even gay gangbangs as the one of the bottom since his mid teens. He only stopped getting fucked and sucking men when we became exclusive. He admitted that in a couple of relationships with older men he crossdressed and likes it.

He has asked me to be with him in a mmf threesome where he gets fucked and I watch. He wants to have sex with me, with a bottom full of another mans sperm.

WTF I don't know where to draw the line.

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# 51253 - by Jen / May 6, 2021

- Fetishes and Kinky Sex -

Straight Male / 23

Mousy, Nerdy, Domme Wife

My wife is also 23 we have been married for 15 months. She is a thin, small titted, mousy brunette. She has a nice body, not super hardbody, but nice. She shaved her pussy for me a couple times before we got married and the night before the wedding. That time she stayed shaved for 4 months. Then she grew it all back in, and I really don't care. No one, not her coworkers, not her sisters or parents, no one at all knows how dominant she has gotten. She showed no sign of it until our first anniversary.

Ever since then she has totally taken over our sex life, she is super dominant and I submissive. I really don't mind her taking the lead and enjoy doing stuff to please her twists and kinks. With a leather collar on, she makes me bend over and she fucks me with a strapon cock. She now uses one that is a little over 2 inches thick and 10 inches long. It is silicone, and flesh colored and even has a foreskin. I get fucked and suck it everyday. While she is fucking me she talks so dirty. She says things that I never figured my little, nerdy, plainjane wife even knew. She talks about how she is fucking her bitch, and calls me a buttwhore, and talks about how she'll sell my whore ass on the street. She has shaved my legs, and trimmed my pubes while leaving hers in full growth. Last week I had to put on stockings before she'd fuck me.

When it's over, though I still wear the collar and I'm fucking her as my wife, she is quiet and calm like always. I really like pleasing her, and no one would know my little nerd is a fuck crazy domme piece of ass.

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# 51786 - by Cal / June 9, 2021

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