Jtc0457

Jtc0457 Avatar
Gender: Straight Male
Age: 51
Relationship Status : Not specified
Profile Visits : 152
Number of Comments : 2
Number of Confessions : 0

Jtc0457's Favorite Confessions:

My Wife Wants To Peg

My wife has been bringing up pegging quite a bit for the last 7 months. She’s definitely more than hinted that she wants to try it. And I should be on the receiving end.

Over the years she’s fingered my butt and stuck a few buttplugs in me. Now I’m at the point where I’m just willing to let her peg me

I went into a sex shop a few weekends ago when I was out of town buying a few things. The woman there helped me get a good harness and a good starter size dildo. I gave her the story about how my wife wants to try it and I’m just not fully convinced yet. But she gladly helped get all the supplies and lube

So while put daughters are at friends houses tonight I’m going to finally g*ft my wife the pegging equipment.

So wish me luck. I’m sure I’ll have a sore butthole in my briefs by the end of the night

Pegging

For months the wife and I have been into anal play. We both enjoy using anal toys and using them on one another. We have been watching pegging porn and to say the least it excites both of us to the point that we decided that we wanted to try it.
About 3 weeks ago we made a trip to the local adult book store to shop for a harness and a few strap on cocks. Both of us got very horny just looking at them and talking about using them. We ended up back in one of the booths licking and sucking on each others ass and she was behind me on her knees with 3 fingers up my ass and my dick in her mouth. We both came twice before we went back to shopping.
Once we got home we showered and the games began. We bought 3 rubber cocks. One tan colored one about 6” long a brown one about 7” long and the last one was a 9” long black one. All 3 are very real looking. We bought more lube and started out in a 69 both of us working on each others ass. After awhile she said she was ready to try fucking me.
My dick got harder just watching her put the harness on. We started out with the 6” cock. I got on my hands and knees and she got behind me and eased it up my asshole. We both liked it so she fucked me awhile. Then we went to the 7” one. She made me cum fucking me with it. She really got in to it and was even talking dirty to me slapping my ass while she fucked my asshole and I came in a steady stream.
I was laying face down by then with her on top of me with all 7” deep in my ass. She kept thrusting it up my ass really hard and then she pulled it out. It wasn’t long before she was back on top of me and I noticed right away that she had put on the biggest one and she was talking to me about taking this big black dick.
She put more lube up my ass and started to work it into my ass. It was very thick and she went slow until the head of it was in my ass. It stung a bit because it was so thick. She was looking at it stuck in my ass and said it looked so hot and then she began to shove it up my ass.
She got carried away making me take such a big cock in my ass.
Before long she was balls deep in my ass and was starting to fuck me. We both got pretty loud and the fucking got pretty wild. I came hard and was laying in a big puddle of my cum as she pounded my asshole and talked very dirty to me. It was the first time in awhile that she squirted and her juices were all over my ass and back as she kept fucking me she finally came again then slowly took her big black dick out of my ass.
After a couple of beers and a shower and cleaning up her cocks we were in the living room naked watching 3 women fuck this one guy with their big strap on cocks. We spent the rest of the day and most of that night with her fucking my ass and me fucking hers. And I used the big black cock on her asshole too.
The next day we were back at the toy store and we bought two much larger rubber cocks and hurried home where she spent a few hours stretching my hole and fucking my ass very deep. I took a big 12” cock up my ass and she really got into using it on me and even filmed it with her phone. By the end of the day she had me fucking the big 12” cock and sucking on another one and she even got me to wear her panties.
I had her tied to the bed face down fucking her ass and shot two loads up her ass then it was her turn to tie me to the bed and she really worked me over good and left me there with the big 12” cock stuck up my ass while she slapped my ass and talked dirty to me.
Now we are both hooked on strap on sex and the cocks are getting bigger and we are both getting our assholes used and stretched pretty often. We now have butt plugs that we both wear around the house and we are looking into other sex toys and expandable butt plugs.
We are both hooked on anal sex and anal play. Who knows where this will end or if it will ever end but all I know is I am really into my sexy wife taking my ass when ever she likes and I love fucking her up the ass. We watch porn every night and both of us have something up our ass most of the time.
We are even talking about having bisexual men join us but not in the near future. Both of us have talked about taking a huge black cock but for now we just watch it on the porn sites and use them on each other. Who knows what might happen one day.

My Husband Is A Sissy

I had no clue when I met him nor for the first years of our marriage. Then I came home early from a weeks trip and there SHE was. My husband who isn't the most "endowed" man in the world was in my nighties, garter, stockings, see through panties and bra. He didn't even react when I came in. He just said hello to me got up and kissed me and sat back down. I asked whats going on and he said it was what he normally did when I was gone. He was a crossdresser and liked feeling feminine. I was somewhat speechless, I'm sure my jaw dropped open. The man who regularly fucks me, eats me, even buttfucks me was actually looking really good in my lingerie. I just said I didn't know what to say and he took me into the bedroom, stripped me, and didn't make love to me he fucked me like when we were first dating. It was extraordinary. He took off the panties leaving all else on, and gave me some of the best sex we've had. After he insisted that I not clean myself, but leave his sperm in me and leaking out, he selected white see through panties and matching bra and a thin shortie nightie. I put them on, me in white him in black. We returned to put some porn on the tele in the living room. He was all over me, kissing me, sucking on my nipples, and rubbing my panties into my crotch getting them all cummy, his and mine.

I finally asked him. He'd been doing this since he was about 12. He used his sisters undies and many times would wear panties under his work suits. Sometimes undies, garter and stockings. I never knew. I asked if he was strictly straight and his answer was "Not strictly". His first sex was at 11 with an older boy. That continued for a few years. Probing further I found out he was the bottom, sometimes the other boy would use his hand on my husband and only a very few times used his mouth. My husband, at 12 - 14 was sucking cock and getting fucked by an older boy. After that boy found that he would wear his sisters undies, it was that way all the time. My husband even now is not that tall, very thin and quite frankly has a bit of a femme body, indented at the waist, legs as shapely that I wish I had them, and the cutest butt every. That butt was one of the things that attracted me to him. Little did I know that it attracted other males too.

His next lover was a man in his 20s. He'd invent "jobs" so he could stay over at his house for the weekend, all the time, dressing in lingerie, undies and even skirts, dresses and blouses for the man and basically being his girlfriend or wife. He says that even when we started dating in college that he had two male lovers and dressed for them. He loved me, and wanted to be with me exclusively so he stopped cold turkey. Until about 2 years before I caught him, he started to dress again. So I accepted that my husbands butt and mouth had more cocks than mine, even more than my pussy (only 3 including hub), and we moved on. He usually dressed late in the evenings, came to bed in sexy lingerie we bought for him. Sometimes I'd look at him and his panties with him all tucked in, actually looked smoother than mine. I do have pretty prominent pussy lips though. He actually looked better than I did.

We had great sex,but then he asked me to use a dildo on him. That lead to a strapon which in turn lead to my wearing mens undies (I have really small boobs, his aren't too much smaller than my little one) and fucking him. He acted totally like a woman when he was dressed, I was having sex with a cock, but a cock attached to a woman, a woman who wanted me to fuck her with a cock. Then I just asked him after several months. He admitted he was getting fucked by a man, he was sucking the mans cock. I even tried to let him have sex with the man while I was there too. I just didn't want sex after that though. The man got very demanding, I thought he was gay but I guess he wasn't. After he fucked my husband my husband cleaned his cock with his mouth, then the man got on top of me and put his cock up my ass. My husband watched, kissing me, sucking on my neck, and even licking the mans asshole. When brad, the man, left my husband had two loads of sperm in his butt, I had one in mine, and one from my husband when Brad made him fuck me while he watched. After Brad was hard and made me suck him and when ready he fucked my husband again.

That was 3 months ago, I haven't had sex since. I don't want it. My husband is happy he is a sissy again, and talks about sex with me all the time. I don't even want to hear about it, but I do.

Crossdress For Sex

This confession may sound made up or off the wall but it's true. I am a crossdresser, I have been dressing since I was in my teens. When I had the chance I would put on my older sisters things and I love how I felt wearing them, so feminine! As the years passed I got married, three kids so all of that stopped, I still had that strong desire but was so paranoid about getting caught and found out. Fast forward......I got divorced, retired and the kids were grown and on their own and scattered all over the country. I live way out in the country and being alone so much I started dressing again, the feeling was even stronger than before and I was dressing everyday at some point and I loved it! I guess it had something to do with age, mid-sixties, but I wanted to dress feminine all the time. I liked the way I looked and how it made me feel make-up and all (which I got very good at) and I felt my manhood slowly slipping away. I was buying things, thanks for Christmas and even Halloween and Valentines Day and soon I had a complete wardrobe. I started watching porn with men and crossdressers and that urge came over me and soon that's all I was thinking about everyday. I went to the adult book store and bought several dildos and to satisfy the urge I would dress late at night then get into bed with my store bought cocks and fuck myself until I would cum thinking this is close to how a Woman would feel. Over time and watching more crossdresser porn the urge to be with a man for real came over me like a tital wave. To get caught would be total humiliation and would surely ruin my life. Nevertheless I continued looking on a site called Locanto and there it was........the ad read "Single Dominate man looking for a Crossdresser, must also be single and must understand I am very demanding". Along with the ad was a photo with a picture of him standing by his pool naked and to say he was well endowed was an understatement. I was not sure about this and after looking over the ad and the picture for over a month I answered! We texted, then we phoned then planned to meet a a nice restaurant the fallowing weekend. As they say it's now or never so we met! The rest of the story is coming!

My Wife Caught Me CD

To keep this short. My wife came home unexpectedly from a long weekend out of town with her family. It was Saturday night instead of Sunday evening like she said. She came in and I was dressed in some of the womens clothes and makeup I keep. I was fully outfitted, flesh colored lace bra, matching lace panties, garter, stockings, a black mini-skirt, white blouse with my long hair styled like a womans, and full make up. I'm thin and not too tall, so I actually am passable as a woman. She came in and I didn't hear her. She came to the back family room and there I am. At first she didn't know who I was. I spoke and she just stood there silent her mouth agape.

She asked if it was me, I said yes and started to explain. "Shut up" she yelled. I was ready for the divorce talk and instead she took my arm and dragged me to the bedroom. Kissing me, making me go down on her, she kept telling me what a hot girl I was and how she loved having another woman eat her out. She was horned up like crazy. She is naked now, I'm in undies, garter stockings only (well my heels) and she turns over, gets on all fours and tells me to fuck her with my strapon. I am going along with it all, and assumed she meant my cock. So I fuck my wife while I'm dressed up as a woman, to her a lesbian having lesbian sex with a married woman. She continued the lesbian charade all night. Eventually turning into a total roleplay. I was her lesbian lover and she the married closeted lesbian. She even had me dress in a shorty nightie as did she when we finally went to sleep. In the morning I woke her with my face between her legs, and after that it was back to real life.

She still hasn't talked about it other than before she sent me into the shower to clean up and change. Tell Sherry I expect to see her again, for a long weekend when my husband is gone. We'll need to buy her some more clothes and lingerie.

I'm in heaven though I wish she and I, as man and woman could talk more about it, but for now . . . GREAT SEX

Mistress And My Only Time Gay Sex

When I was 20 I was in New York for several months for work. I wanted to try to see what it would be like with a woman in total charge. I answered ads for domme women and selected Kara. She was tall, about 5ft. 9in, beautiful face, really tight body, and DD cup boobs that she made me nurse on while in our first interview. She didn't just get paid to domme, she was in it fully as a lifestyle, and wanted to know everything and all boundaries before getting started. My big thing was that I wanted to be able to see my mistess tits, pussy and ass. Other than that I had very few limits i guess.

Soon I was being dressed like a woman, cleaning the apartment like a woman, even changing her pads and tampons. During her period I had to wear a tampon in my butt and a pad in my panties. She had me wearing panties all the time, sometimes with garter and stockings. Once she went out with me in her normal street clothes and me in a thin tee shirt, really tight pants that showed my panty lines and a bra that showed through the thin tee. We went to a movie and dinner, all with people looking at me. It was her way of taking my humiliation into everyday life. That night she had me stay the night with her, I ate her as I did always, if she was satisfied she'd let me jack off, but always had to eat my own cum. On a good day I could jack off on her ass and lick it off. While staying that first night, me wearing lingerie and her wearing gym shorts and nothing else. She started massaging my back and moved to my ass. She was using a lotion and it felt good for a change. Then she got on top of my back and reached down, pulling her shorts down and I felt something at my asshole. She had a strapon cock that even though soft so it didn't show in her shorts it was hard enough to penetrate me. It wasn't too large and she fucked me 3 times each time 30 to 40 minutes. In the morning when she fucked me again it was easy this time. Then I had to take off the strapon and wash it thoroughly and then eat her to get her morning started.

Gradually it got to be bigger and bigger strapons and dildos. Part of my regular punishment was bending over her lap and taking paddlings, from her or other mistresses some just regular woman who got a laugh out of it, then they would watch her fuck me with bigger and bigger dildoes or strapons. Finally she had to two biggest. "If you can take both of these I and mistress charly have a surprise for you, one you'll really like. " I took them both for 15 minutes each. Then Mistress Charly went out and came back in two minutes with a naked man. Not just a naked man, a naked man with a 10 inch cock that was as thick as a damn can of pringles. It was the biggest thing I'd ever seen. My mistress made me get on my knees and ask him if I could honor his cock by sucking it for him. He agreed. In front of these two woman and this strange man I was sucking cock. I'd never had anything to do with another guy before. I sucked and he came filling my mouth, my mistress told me I'd better swallow every drop and I did. Quite frankly I hated the taste.

Then she had me dress and do my makeup, and come out as a girl in sexy undies and I ate both mistresses, by then the man was recouped. My mistresss told me he was tested and disease free, so I had no worry. They watched us get into bed and I sucked him hard at their orders, then my mistress lubed me and his cock, then they watched me get fucked. After I had his sperm in my ass and my ass gaping open, they both left us. He had me for the entire night and the next morning. After getting fucked again in the morning I made him breakfast still in my lingerie. My mistress came in, I made her breakfast, and the man left, just as naked as he came in the night before.

"Did you take care of your husbands needs last night?" she asked
"Yes Mistress I did, four times" I said
"Good, one of these days you'll make someone a good little wife"

I never went back to her, and in a couple of weeks I was done with my work and went back home. I started dating a girl I knew in high school, got her pregnant and we got married and have been ever since. I've only had m2m sex with one guy for one night in New York, and I never tell anyone. Looking back I guess the next morning with his fresh load deep inside me and cooking him breakfast, I felt really like a wife. I look at mine in the morning at the breakfast table and know that I am very familiar with what she's feeling.

Woman Crossdressing

I do it for my bi hubsand. I am pretty thin, kinda tall, straight body no waist, and bee stings at the nipples. I was called "flatso" at school. My husband always liked my body, I thought he was gay for over a year when I met him, but he soon showed me that he was definitely not gay. I had only been with 4 guys, 3 of them at the same time. Those three were my first and they had sex with me for a couple of years or so, sometimes all 3,sometimes 2 or individually. I went on the pill because none of them would use condoms, I talked to my mom about getting on the pill and instead of lecturing me about being 15 and having sex, I think she was relieved that a guy (she didn't know it was 3) would fuck me with no boobs.

I sucked them all, and got fucked by them all, eventually one of them stuck it up my ass to my screaming and trying to wiggle free. At least all that wiggling caused him to cum quickly. After that anal was part of the play with two of the guys. After highschool I let one guy have sex with me in college and after that he never came around me again. I would see him with other girls who were really big on top.

Enter my now husband. It was nice hanging with a guy I thought was gay, no pressure, no issues with my boobs, or rather lack thereof. When it came around, sex with him was GREAT. He kept hinting at anal and I let him do it of course. With him it was always with me on my belly and him on top of me, or occasionally doggie. He was of course still sleeping with other guys, in asking him about it, he was the top. He'd tried the other way and didn't like it. I guess with me he had 3 holes instead of 2 and one day when we were still dating I came to his place in jeans, a white tee, high top tennis shoes. I'd cut my hair short and when he took off my jeans I was in Jockey mens underpants. He tented his pants immediately with the biggest erection I'd seen from him yet. I still do that and I get orgasms from anal, from vaginal, and he gives me both, but when I crossdress for him as a guy, he can't get enough.

I love him, he loves me, yes I "pretend" to be someone else sometimes for him to help him keep being excited. We've gone out in public as a gay couple, as a straight couple, I've got to beaches with him as a boy and many times I have on boys underpants even if I'm in a skirt or dress. I think of it as the same as when I shave my pussy for him, or trim it in different shapes to keep things exciting. I've even dyed my hair down there for him and on my head to give him a "natural" blonde and redhead. In a way THAT is the same thing as being a different person to keep it exciting, just like my crossdressing as a guy for my husband.

Surprise First Time

My extremely hot Asian girlfriend and I were laying on the bed naked and kissing. She then stopped kissing me and asked if we could play with a dildo. It sounded fun so I said sure and she got up and came back with her biggest dildo. We started making out again as she slowly moved the dildo up to our mouths. She started sucking it like she would with my cock and I got even hornier. Then she shoved it in my mouth and since I was so horny I started sucking it too. We took turns kissing and sucking the dildo, eventually I asked if she wanted me to put the dildo in her. She laughed and told me to lay down. I laid down and then she sat her beautiful pussy on my face and said the dildo was going in me. Her pussy tasted too good and I was so horny that I just moaned a little in agreement. As she sat on my face she pushed the dildo up against my asshole and started massaging the area around it. I moaned some more as I heard her open the bottle of lube and move the dildo away from my ass to live it up. I was scared as this was a really big dildo and I knew she had smaller ones but I wasn’t going to stop her as I was too curious now. She told me to lift my legs and spread them. I held them up as she tried to put the dildo in my tight asshole but it wouldn’t fit. I then took my hands and spread my ass wide and told her to force it in. She shoved and it popped all the way in. She then moaned and took her hands off the dildo which immediately came out. I moaned loud at this. She just laughed and slammed it back in. At this point she moved forward a bit so that I was licking her asshole and she was fucking mine. She moved the dildo all the way out and would then slam it back in. It felt so good, I was in shock and not even sure what was happening, I just knew I wanted more. I then told her to fuck me hard. She took the dildo and vigorously thrust it in me as deep as it would go. I felt pure ecstasy as my ass got pounded by her for 10 minutes straight. During this time my dick swayed back and forth limp but I felt like I was about to cum. I moaned to her that i was going to come and she went even harder and faster. I came so hard from that as one long stream of cum came out of my limp dick. It was the most insane orgasm of my life. Eventually she stopped and got off my face and angrily told me that she never said I could cum. She then took my cum and scooped it up with her finger and put it in my mouth. She made me eat all my cum as punishment. She then made suck on her small but gorgeous tits for another 20 minutes as I fingered her wet pussy too. As our sessions came to a close she said that my punishment was up and laughed as she said I should only cum with her permission. Now I have a fetish for being dominated by small Asian women after being fucked in the ass for the first time by one. As time has gone on I have become her submissive cuck that gets pegged regularly and I wouldn’t have it any other way.

Two's Up

There are two older sisters (40's) who live together at their cottage about half a mile from my place.
And both sisters are being fucked by one guy, me.

They're both very keen swimmers and both enjoy extremely kinky sex.
I met them at a river swimming event last summer and both women began chatting me up.

I didn't know they were sisters at first even though they had the same swimming costume on. So as a kind of joke I asked them if they shared the same man.
Without any hesitation they both said they'd gladly fuck me together.
Trust me, they were far more forward than I was, and believe me even though they're in their mid forties, it's not easy keeping up with them sexually.

I was invited round the same evening and within half an hour I was naked, having my cock sucked and my face pushed into the older sisters pussy.
I went on to tongue and fuck them both, with the younger of the two enjoying anal sex too.

When I walked the half mile back to my place later on, I was totally knackered, but knew I wanted more.
Unfortunately because of their working schedule, I've only had sex with them both together three more times.

Mostly I get to fuck the older of the two, but I much prefer fucking the youngest as she's such a sexually inventive slut. And she does something for me I've grown to adore.
Whenever she sucks my dick, she'll also rim and finger my arse. It feels incredible and she'll also finger my rear hole when we fuck missionary too.
I cum so violently with my cock up her tight c**t, her tongue down my throat and her fingers probing my arsehole.

They're not the best looking women, but believe me they're utter sluts and I'm loving the sex. Plus neither want me around permanently, which suits me just fine.
As the oldest says to me "You're our walking dildo".

The Couple Around The Block

I met them doing pool duty in their yard. She would come out in the skimpiest of bikinis, if you can call three patches of material and some string a bikini. She would always let her tits fall out and not even try to cover up. If I was near, she'd actually be sunning and reach down and pull the patch over her pussy over so I could see it in its waxed wonder. She'd do it in front of her husband he wasn't much better, he'd just blatantly strip while I was around. She and he both would make sure a robe slipped open in their house so I could see them. She left the kitchen and he told me that she was really interested in having sex with me, but only if I was inexperienced. I was, in my mid teens and wanting to be with a naked woman so bad, I was ready for anything. He had me strip saying she was waiting for me in their bedroom and ready. Naked standing there, he started jacking on my cock. "Don't cum too soon, she'll want the first load in her mouth, then you can take a while in her pussy, she loves to introduce boys to a woman".

Then the bomb dropped, I'm hard, I'm naked, she's standing now in the doorway, playing with her tits and her pussy. "Do you want her" he asked. Of course I did. Then the agreement, first I had to blow him and he would leave me alone with her. Then after that it was simple, she'd get me used to it so it wouldn't hurt, but he got to get blown or fuck me twice for every I fucked her. She chimed in, "Well, what do you say? I can't wait for you to come to me, and cum in me "

He was sitting on a kitchen chair. He said "just get on your knees between my legs and we can all have some fun" I didn't really dwell on it, she was pushing her hips forward in my direction, she was behind him I just knelt down and got between his legs and his 8 incher was in my mouth. I'd never had a BJ but I knew what to do and did it. It took him probably 15 minutes, my jaws were getting tired and he blew off in my mouth. I tried to swallow, I choked a bit and some dripped back onto his cock. He pushed my head down and I licked the rest up and swallowed. "I'll have Maggie send me a text when you two are done, then I'll take my second time after she's finished" then he stood up, put on some pants and a tee shirt and left.

I got a BJ first, she was kissing me so much before, she kept talking about how I smelled and tasted like her husbands cum, and then after my BJ she fed me some of my own cum, and kept kissing me telling me how hot she was getting knowing I had tasted both my cum and his. I had her husbands cock in my mouth. She took time before letting me fuck her to play with my ass. She was showing me how to push out when something was going in to ease the entry. She was soon fucking me with three fingers. Then a vibe was inserted, it hurt till she turned it on, that is the way I fucked her. A vibrator in my ass and my cock inside a beautiful woman. After we are both laying there, and he came back. He pulled the vibe out of me, it was already turned off, and she put one of her plump tits in my mouth and kept urging me to push out while he was pushing his cock into me. It did help. I laid there with his wife watching me get fucked by her husband, her kissing me, me sucking on her tits, and finally she pulled herself up to have my face between her legs, I was eating her pussy dripping with my cum while her husband was filling my ass with his.

This went on for several years till I was 18 and had to leave for college. They were true to their word, every time with her, whether her mouth, or her pussy, she didn't do anal. He got me twice. I actually came to like it from him. I liked knowing I was making him and his cock feel as good as she did me. He only blew me once, and I never fucked him, I was always the bottom, just as she was for me.