My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.

Nailing My Sister-In-Law [M/f]

It was a hot summer day in late May. This summer would be the hottest on record for sure I thought as I just got in from a morning of doing yard work. I just went to sit down in the A/C and watch some TV when my wife came up from the basement.
“Get over to my Mom and Dad’s house and put the window air conditioning units in for my sister,” she ordered.

I looked at her thinking are you serious…

I just nodded and put my sneakers back on and went out the door back into the heat to do the task. My in-laws lived in town and my mother-in-law was out of town and so was my father-in-law. My 19 year old sister-in-law just finished up her first year of college and was clueless when it came to this stuff. Plus she could not lift the big window units by herself.
I arrived at the house and walked in the front door. I thought to myself how the hell can it be hotter in hear than it is outside. I hollered for my sister-in-law as I walked in the door, “Mandi where you at.”

[Humorous] Had a pretty weird and NSFW night driving for Uber, recounted it for your enjoyment

Had an interesting night driving again, every night seems like it gets crazier than the last and it has kept that trend for almost 2 months now. It was more interesting for more reasons than just one, but the last one and most out of character for me was being invited up to an apartment (which normally I would decline) at the end of my typical retiring time in the early morning and accepting the offer. It was a third person experience—I was watching from somewhere up and behind everything, think about an RPG video game camera angle, and was surprised by the turn in the dialogue. I followed her up, and while smoking a bowl and drinking a Mikes Hard Lemonade (no that isn’t product placement, and no I don’t have any affiliation with Mikes Hard Lemonadetm) we talked for about 5 minutes about random pointless shit. I noticed she had Seinfeld on (fucking great show) and then I basically threw my face into her chest.
She was curvy and self conscious about it for some reason, maybe some douchebag guys or girls had given her shit. Anyways I was always of the mindset “more cushion for the pushin’” so I tried to put her to ease. After stripping our clothes I proceeded to fuck her brains out (and she mine for that matter) all over her bed and bedsheets her vag had soaked. I made her cum 3 times (her count, maybe she was being nice) before she basically ate my dick and swallowed my bastards RIP.
Anyways she was a sweet girl, god bless her. She rode me and broke me in like a young buckin’ colt to boot. Unfortunately I forgot her name already cause I’m pretty much a douche from earlier myself. She seemed really eager to get my contact information afterwards. I was pretty much halfway out the door and made up some bullshit excuse as to why I couldn’t have her text me, and why I would text her in a bit, which I wasn’t going to do
fortunately I did text her because what happened next was hilarious and has me wondering something. I had left my phone, keys, wallet and 60$ in cash on her bed stand and threw everything on so quickly I thought I left the cash. I went up to her place and went back in, door was open when I had left. She was surprised (obviously) but when I told her that I had left something she starting pacing around frantically looking for it without even knowing what it was yet. I mentioned it was 60$ and she almost had a full on panic attack. Lol.
(FYI I had the money in my other pocket, and my dumbass self hadn’t checked the other side of my pants as if I had no goddamn sense) but here I am in her messy ass room, her still half naked running around flipping over a fuck ton of clothing looking for the money already in my pocket. I am standing there thinking ‘fuck it even if she took the 60$ just get the fuck out of here and don’t look back’ and ‘I just had sex with a prostitute didn’t I? Oh well.’ And then right about……now… I notice, oh nice it is in my other pocket, she is still having an incredible meltdown in front of me all the while. I almost felt like she had pretty much given up hope on me wanting anything to do with her again, she might have been right. Now that she was so visibly hurt at the thought I would accuse her of stealing it, and obviously I know she didn’t, I almost felt bad for a second. She legitimately felt bad. She wanted nothing more than to find that money. She was considerate. I thought ‘know what? I could make her happy. And you know what else? She could probably make me happy too.’ Then, instead, I told her to not worry about it and to text me later when she found it (which she wont lol again).
I wonder if she’ll text me that she found it? That is what im interested in at this juncture. Now I am not deplorable enough to actually accept the money, give me some credit I was raised with morals. I would just forlornly tell her to not worry about it and to keep the money, and proceed to never release her or this night from my headmeat vault to a living soul. What does it mean about me as a person to have treated her this way in less than an hour of knowing her?
I can’t be with her, despite her overwhelming desire to be with me—she wasn’t a bad person in anyway, just not for me. Something awned on me at that moment—a shower thought if you will. What if that is how intelligent women (who I happen to have a thing for, and never seem to get duh right) have to navigate the world? Always shielding off a horde of horny apes just to find the one guy that isn’t a dick on legs? I thought about how porn and PG porn, aka TV, conditions us to be ok with objectification and how it had affected me this very night. My new friend taught me many things about myself funny enough and who knows, maybe a new horizon in my existence. I just can’t stop thinking about how her pussy tasted sour.

The fourth threesome got a little weird (in a good way) [M21/F20/F21]

EDIT: Apologies, the end of the post title should read [M21/F20/M21].

Like my other stories, this one is 100% true. This is another threesome story from an ongoing sexual relationship my girlfriend, a close friend of mine and I had for a few months while in college, for more background, see the previous stories below, however essentially the back story is that my friend ended a long term relationship and my girlfriend offered take care of his physical needs for a while until he was ready to start dating again. Over a period of several months my girlfriend would frequently meet up with my friend and either jack him off or blow him, occasionally though, we would have a threesome together.

Previous stories are here:

https://www.reddit.com/r/gonewildstories/comments/4ad4ap/first_threesome_with_girlfriend_and_friend_mfm/

https://www.reddit.com/r/gonewildstories/comments/4ahv5y/minibukkake_with_girlfriend_and_friend_mfm/

https://www.reddit.com/r/gonewildstories/comments/4amy7i/threesome_on_the_beach_m21f20m20/

On this particular night my friend came around and we had a few beers and watched some TV. We sat on the couch together, with my friend and I sitting up while my girlfriend lay down over us, her head on the arm of the couch, chest over my friend and her legs over me. It was a warm day so she wasn’t wearing much: some shorts that barely covered her butt or her hips and a cut-off top that exposed her stomach. I’ve described her in previous stories, but she was a cute little brown girl with shapely tits and a curvaceous ass.

First time with a shemale

she-male experience
I have alway had a fantasy with being with a she male for years I find them beautiful , exotic and until recently I found out its something straight men are naturally attracted due to them being so fem. Its the fact there are woman with penis with is the holy grail.
One day I am looking at she porn at shamble gods.com and I decided to look on craigslist and just look if there any in my area. I find one and answer to an add to a woman called she-male jem, she is looking for a bottom boy for the night. I send her a pic and responds to me back with her number and we talk for a little about what we want to do. This is a pic of what she looks likehttp://img.adultsearch.com/classifieds/798345_0uiaw18lT0oOKudJtFT.jpg and this is a pic of her cock http://img.adultsearch.com/classifieds/798345_74OFetCTBEJlzYLz2CtU.jpg
it looks nice and big and like the previous story that I want a prostate orgasm and experience a beautiful woman with a cock =). She instructs me to go buy condoms and she has lube. So on my way to go see her I stop at a gas station again but this time a chicken out because I didn’t want to be judged buying condoms. =(
Once I arrive it looks like a really bad area and i start to get scared. I was about to leave but she came out greeted me while I am in my car and told me to come and fallow her into her apartment. Her apartment is really small and by the looks of it she lives by her self. I laugh a bit because there is porn on when I enter the living room and we talk about ps3 and how she knows how to fix them.
When I first saw her with my eyes I realized she is really tall and she is beautiful and the pics she sent me do no justice, she looked way better in person and even better than her porn videos. We talked and she told me, she was a porn star for a while for she-male strokers and she told me stories how men with there wives would recognize her at the stores.
After a while she asks me what turns me on?
I reply “I love thongs”! like from my first experience with popping my cherry I lost control of my self when I saw the skater girl in just a thong.
She tells me is a sarcastic way “I am not wearing any underwear” and I look down and she was just wearing a skirt and I see her beautiful cock hard and it puts my 5 and half cock to shame. it looks huge and tasty and warm.
I am dumbfounded and with my jaw open I ask her if I can suck on it and she replies “yes with a giggle”. Know this is my very first time sucking on a cock at all and especially at this size its huge. I lick the head gently like ice cream hoping to get that cream filling at the center.
Then I finally put it in my mouth and I am moaning with so much excitement. I am kissing her cock, smelling it, rubbing it and trying to take as much as I can in my mouth. I can tell she is getting really Horney.
She asks me did you bring the condoms? I reply no because I become scared and she looks at me, with so much disappointment. she just tells me to keep sucking and finally I pull my pants down and I grab our cocks together like I am stroking just my own up and down together. it really feels nice to rub a cock on another cock.
She asks me “is there anything you want to do?” I reply I have always wanted to 69 and we do just that. With me on bottom of course =) and her cock and ass in such perfect view I start sucking and at the same time she is sucking me good. like omg !!!!
Then finally I hear her say “screw it I can’t take it anymore” and puts me an my all fours on the coach and asks me if I have ever had sex with a guy before and I lied and said no ,because The other story with the guy.
She puts lube on her finger and goes in me it felt so good entering my tight little boy pussy and then puts some lube on her cock before entering me. Now this cock was way better than that guys cock before. I felt so much and she was way better in every way. She tells me that I am so tight =). She is really making my ass stretch to its limits. After going in slowly she finally all the way in me. Then here comes the best anal sex I have ever had in my life.
She pounds me at a long slow pace at first it feels so good I can feel it through my whole body. my ass is being dominated by the hung shemale and I love it so much. and at the same time she reaches for my cocks and is jerking me off with her in my boy pussy taking in her cock.
It gets bad to the point I am moaning so loud I wonder if the next room hears me getting fucked by this beautiful woman. She is sending me shockwaves through my body aching for my prostate fun.After a while she asks me where does she wants me to cum? I tell her to cum in me because I want to feel her load in me and wanted to see how it felt. Her cock starts to throb in contractions and She cums right in me with her perfect load in me and my ass is eating every last drop. She is moaning in excitement and her cock is drained from my ass =)
Next she tells me its my turn and I tell her I have never gave anyone anal before and she smiles and says “nice this is going to be your first time.”
She tells me sit on the coach and I do so and she is standing over me with her ass at my face level and slowly puts her ass hole right on my cock. She starts to put her body weight on my cock. She starts and slow adjusting her pro ass on my cock then She is bouncing my cock and I feel the warmness tingles sensation of me cumin and I ask her the same question right before I let go of my seed “where do you want me to cum” and “she replies in my ass and I my cock shoots my load up her dominate ass. =)
When she gets off my lap my dick pulls out with such force it hurts and she giggles. At this point my cock is to senstive.
When I am leaving she is naked telling me goodbye with her door wide open and she told me “you are going to see me again”. =) Which I still crave that dick sadly. And before I leave I hug her naked body next to my own with clothes and tell her goodbye and I secretly wanted to suck her goodbye and taste my own ass of her cock. but I left to crave her cock once again.
I went to sleep with cum in my ass dripping till morning and I loved it. =) Yes I do love shemale and still want to get dominated by a strap on.

Spring Break got a little crazy [m/m/f]

So I just got back yesterday from a 4-day cruise and really want to share this story with you guys. I’m a 21 year old college student going on my first real vacation where I can drink alcohol and not with my parents, and going with a bunch of other college-aged people so I was excited on the partying that was sure to happen over the week.

After I strike out the first night, the second night on the cruise I hook up with a smoking hot blonde named Sarah from a southern school. I’m from the north and was turned on by her southern bell accent and her great ass I saw on the pool deck at the start of the day. She was about 5’5″ and looked stunning in a bathing suit or in a dress. She had curly-ish hair and had a more cute than hot face, if you guys know what I mean. This story really isn’t about that night though, I’ve hooked up with girls before and the sex was nice, but nothing totally awesome. We fucked in doggy and missionary and I came on her back.

Sorry Bob, your wife pays my rent [MFM][cuckold][prost]

Standing on her doorstep, I put some gum in my mouth, cranked my head side to side, toughening up into a rough neck dressed in a plaid cotton work shirt, jeans topped with a big rodeo buckle. It felt like Halloween to me but this is what she likes. I rang the doorbell, feeling the warmth in my loins from the dick drug I took 30 minutes ago. With her, I need Viagra.

Patricia answered it dressed in a purple satin slip and matching robe. She was tipsy, wobbling in mule heels with a tumbler of bourbon on ice in her hand.

“Hello, lover,” she said, gesturing for me to enter.

She had one of those western themed house with oversized leather furniture, pony skin pillows and Navajo rugs, all under a glass eyed gaze of stuffed big game animals scattered throughout her home. A Patsy Cline song crooned on her sound system.

She said, “You’re looking delicious tonight.”

“Thanks.”

I stood in her foyer, not taking another step until I get my fee.

“Oh, here,” she said, handing me an envelope which I opened to confirm seven one hundred dollar bills.

[F]isrt So[m]nophilia Experience

*I haven’t posted here in a while, but I’m hopeful that this story will be worth the wait. Enjoy!*

———————————————————–

My relationship is the most sexually backwards relationship I have **ever** heard of. It’s actually **me** who wants sex, a 23-year-old female with short brown hair, a pretty average build, and what I’ve been told are a “very perky, fantastic” set of C’s. Meanwhile, my 23-year-old boyfriend is content with once a month or less even though I regularly pursue him. It’s the **one** thing about our relationship that I genuinely hate. Everything else is great. We match so well in every department *except* for our sex drives. When it does happen though, boy does it make up for the wait.

My first experience with a crossdresser [M18, T25]

For this story, I’m returning right back to the beginning. This was about ten years ago, but as with first experiences for many people, the vivid details have stayed with me to this day. I was 18, and at the time had begun partying. I live in a jurisdiction where the drinking age is 18, so as you can imagine, we liked to let loose at the weekends. I don’t drink now, and drank very little alcohol at the time, so my partying usually consisted of me driving my friends to a club, dancing a bit, try to get a girl and then head home. Obviously being relatively sober around drunk girls had its advantages, and many times I had girls hanging over me because I could make them laugh. Or more properly, I could speak coherently, while they couldn’t.

I’d already been into crossdressing porn for a few years. This was 2005, YouTube had only just started, and streaming video was very much in its infancy. In fairness, we already had broadband Internet, so it wasn’t terribly slow, I think in or around 2mbps. Despite that, streaming porn had barely taken off. I constantly fantasised about crossdressers, but usually I could only get that fix by images. Hardcore porn movies mostly featured so-called “shemales” in those days, which weren’t then and to this day aren’t my thing. The odd crossdressing video I could find left me cumming for days. I fucking loved it.

A Tale of No One – Chapter 3 [MF] [BDSM] [NSFW] [Romantic]

A Tale of No One – Chapter 3

DISCOVERY

Alix spent all of Wednesday wrangling with her emotions. At first the shame fed the depression and then the depression deadened everything, which made it easier to get dressed and go to work. The eyes of her co-workers were tough to feel on her, after all everyone had by now heard how she stayed late with the client, even if they didn’t know the rest. Whatever they assumed happened last night was probably worse than the truth. She had submitted to a stranger who in turn spanked her until orgasm, but this was somehow less humiliating than being a slut who slept with a brutish looking man because he was rich.

But just as the depression was enveiling her, she remembered Robert’s admission that he had come to long for his depression, and that it was like a warm blanket that wrapped him up and absolved him of responsibility. This pushed it away, like a admonished child. Whenever it fled, the excitement she felt the night before would make a brief appearance, like a photo flash, to remind her it was still there. But so too would the shame return along with the loathing of her own needs, now with a healthy dose of confusion. Something in her responded to giving up everything to him. The surrender, the pain, the punishment, it was as if giving that to someone else she no longer had to do it herself. I give you control. She thought.