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My She male experience was HOT!
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Every once in a while, I like to do a masturbation session in which I get dressed up in sexy lingerie! I love adorning myself in black, thigh-high, fishnet stockings, black garter belt, and lacy little black panties. I prance around in front of a full-length mirror while I jack off with my left hand and spank my ass with my right hand, saying out loud, “Come on, jack off, you little sissy girl, dance and prance and show us how you jerk off, you little masturbator.”
When I was younger I had a strong urge to go out in drag in public and imagine being a real girl, wearing not only lingerie, but also black high-heeled pumps, red satin long-sleeved blouse, short black mini-skirt, shoulder-length wig, and make-up, including mascara, eye shadow, and fire engine red lipstick. Unfortunately for me, I soon discovered I’m not very convincing as a girl. Even when driving along a city street, and only my head and shoulders visible to other vehicles, a passenger in a car in the next lane shouted out when passing me, “TV or not TV, that is the question!” That totally destroyed my image of myself as a sexy girl, so now I only dress up in private.
However, when I was much younger I did some public crossdressing with limited success. For example, many years ago, when my wife was away for a 5-day yoga retreat, the urge to cross dress started growing stronger and stronger in my mind until I decided to give in. I responded to an advertisement in an alternative newspaper and set up plans to visit a sexy looking she male and to visit her while cross dressed like a woman. I went to Ross Dress for Less and bought a pair of women’s size-12 black pumps. Then I went to a costume store and bought a shoulder length wavy-haired wig. The rest of the outfit, described in the previous paragraph, I borrowed from my wife’s drawers and closet. I spent an entire afternoon primping and preening as I got into my feminine attire trying to elicit my feminine self. I am easily lost in the feminine mystique. Almost any pornographic photo of a woman makes me feel tremendous sexual desire at a very basic, visceral level. On the other hand, I’ve never felt anyone look at me with that animal lust sort of desire for my male persona. As a man, I don’t feel sexy – I only feel inadequate, puny, despicable. Only when I cross dress do I actually feel desirable, feel, well… sexy, actually sexy, like a woman must feel when a man stares at her curves, as he leers at her legs, her ass, her breasts. That’s the feeling I try to experience when cross dressing.
It was a fairly long drive to my shemale consort, Sally’s, apartment. The anticipation was so powerful that, I made most of the drive one-handed, as I had my hard cock in the other hand, keeping my pleasure activated, imagining the excitement to ensue. Finally, I arrived and found a parking spot about two blocks from Sally’s apartment. My heart was pounding as I walked along, twice passing couples moving in the opposite direction, putting my head down as we neared to hide my face, which I was sure would be a dead give-away. I was delighted when Sally answered her door looking very feminine and flashing me a pleasant smile. She looked me up and down and said, “My, my, aren’t we sexy today!” She stepped back to let me enter, and then we both stared at each other’s bodies for a minute.
I complimented her and said she was perfect for me. I asked if I could explore her body with my hands and she said, “Easy, honey, first let’s see what you’ve got there, do a little strip show for me!” She played an Al Green album, and I started dancing, slowly at first, and then boldly as I started stripping out of my blouse and skirt, down to my panties, garter belt and stockings. She said, “Panties, too.” I obeyed, slipping out of my panties, revealing my erection. “Now really dance, like a stripper.” Again, I obeyed, hand behind my head, hips gyrating, cock flopping, enjoying the sensations of being stared at while I existed on the border line of feminine and masculine.
Then Sally reciprocated, dancing and stripping and smiling and removing her blouse, revealing the curves of her breasts encased in her black lacy bra. She looked completely feminine. Then she unzipped and lowered her skirt revealing the smooth hairless skin of her abdomen and hips and thighs. And then, revealing a garter belt and stockings similar to mine, she put her thumbs inside her panty elastic and slid them down. Her cock popped out, about the same size as mine, hard, shiny, urgent.
She danced closer and closer until our hips were nearly touching. She reached behind her back with both hands and unhooked her brassiere revealing the full roundness of her breasts, nipples erect. Next her hands found mine and moved them onto her breasts. I don’t know if they were hormonally or surgically created, but they were purely heaven to fondle. Sally continued to sway to the music, as did I. Our eyes occasionally met, and she smiled. I moved my hands over her shoulders and arms, so feminine, her back, her abdomen, and her ass cheeks, where they rested for some time. She ran her hands over my ass cheeks as well. Then I moved my right hand around her hips and gently grasped her cock, just enjoying the feel of holding a cock other than my own, feeling its heft and hardness. That was a wonderful moment for me, to be close to a woman with a cock, so feminine, so masculine.
Eventually, I started caressing and stroking her cock, and she soon reciprocated, each of us masturbating the other’s cock, such pleasure! I love to masturbate my own cock, but was equally enjoying masturbating a she male cock! I then moved closer still, so our cocks were touching each other, and I moved my hand so it was holding both cocks at the same time, rubbing them together, the head, the shaft, the two cocks humping each other.
Sally invited me to her bed, and laid down so that we were in a 69 position. She was quick to action, which I thoroughly enjoyed, but I took my time, continuing to play with her cock with my hand – I just loved jacking it off while it was right in front of my face. Eventually, I stuck out my tongue and licked – it was so warm, so smooth, so hard. I spent a lot of time licking the glans and the area just under the rim, round and round. Then I wrapped my lips around the head and I swirled my tongue round and round the glans. Sally responded by humping her hips, and I responded to that by bobbing my head up and down, letting her fuck my face. Next, I suddenly felt her finger move from my ass cheek to my anus as it probed and entered me and she started finger fucking my asshole! I could barely keep from coming right then! I decided to do the same to her, and it clearly increased her excitement!
After some time, she asked who’s going to fuck whom. I said, “Let’s take turns, you fuck me first. I’d like to do it facing each other, OK?” We sat on her bed facing each other and we jointly rolled a condom onto her cock. I lifted my ass up and raised myself up over her cock like I was about to sit on her lap. She again put her finger up my ass, added some lubricant, and then finger fucked me vigorously with two fingers. Then surprisingly easily, she replaced her fingers with her cock, and with a bit more lube, started jacking me off while fucking my ass. At first we rocked very slowly, and then eventually, discovered a rhythm of moving in opposite directions to achieve the deepest penetration. Being fucked in the ass is such a different feeling from normal sex, to actually have a cock inside myself, to be filled up, to be taken, to know the cock inside me is deriving pleasure from fucking me.
“Okay, let’s trade,” Sally said. We did everything exactly the same, except reversed, my cock up her ass, my hand masturbating her cock. As much as I liked getting fucked by Sally, I liked fucking her ass and jacking her off even better. It was such pleasure to have my cock inside her, fucking her, but what really got me was jacking her cock off like it was my own, like it was part of me, right there in my crotch, pointing up at me, all glistening with lube, so hard, so shiny, so needing to spurt! It didn’t take long and I was about to come. I told Sally, and she said, “Yes, let’s come. I’m ready, are you?” I think she let out the first cry of orgasm, and that sound of pleasure just ignited my cock into an eruption so that as I shot a load up her ass, at the same time she spurted her come, which arched into the air and splattered on my chest and belly. It was like having two cocks both release at once!
It was a little awkward getting dressed again, now that I was de-spunked, my libido and desire for going out dressed in a mini-skirt was a lot less keen. But the humiliation is part of what got me into this in the first place, so I made my way home, replaying the action scene by scene, catching myself grinning most of the drive home.
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Posted on : Feb 26, 2019
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Add Comment
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Commented on Apr 21, 2020
i'm so glad you read this story a second time and masturbated to it. Like you, I think I'm developing a "cock fetish"!
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Commented on Apr 20, 2020
I read this story again, this time i masturbated while i was reading it.
I've never had a real cock in my ass, although i've put many things down there, even dildos.
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Commented on Mar 4, 2019
And did you masturbate when reading my story? Tell me if and how you came. And have you had a similar experience?
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Commented on Mar 2, 2019
Hot stories!!! i love them
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