I Kissed a “Girl” and I Liked It, Part 2

Oroblu Bustier and Thong

It’s not often that I go on a date with another crossdresser but I too often question myself as to why not just have a little “fun” when I can. So I did and what a rush it was! So here is my little kiss-and-tell of that one very unforgettable date. Note that the name of my “significant other” has been changed to preserve her identity.

Read Part 1

Sharon giggled for a second and made a humored attempt at an access hole through my pantyhose by poking her rock-hard cock into it several times while I’m on my back with my legs pulled as far as they go. As I anticipated her “entrance,” feeling her cock in and out and just barely teasing my ass was, in fact, a turn on. The tease made me so wild with anticipation, I start to tremble from the excitement.

Yet, realizing that the nylon and spandex was tough to break, Sharon ripped a small hole with her fingernails just below the crotch area and gently widened it exposing my asshole-turned-vagina. I even noted to myself, it would have been wet as possible if it weren’t for those damn gender differences. Oh well.

I grabbed a condom and lube, conveniently laid ready in place on the bed, and unrolled the condom onto her cock in a smooth, single stroke. Next, I squirted a little lube into my hand and softly stroked it over the condom-covered-cock while she let out a slow “Ooooh.”

Sharon was very gentle at first, easing her slicked love rod through my sphincter which penetrated with a little resistance but gave me a shock of excitement throughout my body. I remembered thinking “Oh my god, there is a dick inside me!” Even a wave of panic came across me.

“Am I really being fucked in the ass?” I thought for a moment. “Should I be doing this?”

It wasn’t my first time, though, so in that exact same moment, I consciously decided to calm the hell down and enjoy the experience. Otherwise, things can go south rather quick which I did not want to let happen.

“Yes, I should little bitch,” became my next thought. No going back then.

Sharon entered deeper, then deeper with her first few slow thrusts until finally making full penetration. There, she held her love rod in place while grabbing each of my straightened legs and pushing them back, using them for support. She flattered me by mentioning I have sexy, flexible legs which then gave her the green light to do whatever she wanted. I mean anything.

The real fun started, though, as she fucked with just more force than before which sent me through another wave of excitement, an exhilarating body high. I had always practiced anal penetration with a dildo a similar size to Sharon’s cock, however, the real thing was WAY different. There was no match of the sensation of hot flesh pounding me from the ass masturbation of a hard rubber dildo I was used to. This was definitely something I could easily get used to. Oh, and any guilt and second thoughts I had… turned into shame as to why I haven’t been doing this sooner.

Sharon continued pounding at my ass which began to make a muffled clap as we both moan, in rather respectable girly voices I should add. I’m so into our crossdressed banging that I scream out “Harder!” which Sharon obliged without hesitation. The clap got louder as well as our girly moans. The sensation I received, though, suddenly went into overdrive. Not to be disgusting, but it felt somewhere between being electrocuted and taking a shit at a hundred miles per hour. Strange, yes, but very satisfying at the moment as I tensed up tightly clutching the bed with my hands.

Then her moment came, or better said, was about to come as she made her final thrust and pulled out, seemingly not wishing to explode just yet. That’s when an idea hit me and I slipped the straps off of my bustier pulling it down to reveal my “boobs” which, believe it or not, had a slight womanly shape and femininity to them.

I pressed my perky breasts together creating a small but sufficient cleavage for Sharon to finish her work. Without even a word exchanged, Sharon slipped off the condom and used it to wet down my boob tunnel with the lube that remained. Then she straddled my body taking position over me as I continued to press my breasts in place.

There was no delay as Sharon fucked my tits, hitting my chin with the tip of her cock with each pass as I looked on with a front row view. The pitch from her moans increased as she neared climax while I let out a few token moans that more or less cheered her on. Then, suddenly, I felt a warm splash on my face and lips as Sharon finally came… and quite a good amount, too, leaving a hot gooey trail on my face and neck and all over my lubed up cleavage.

“You’re delicious,” I said while licking a little of the cum from my lips. The taste of her love honey mixed in with taste the minty lip gloss I had on was quite arousing to say the least. In the same moment as I savor the taste of my crosslover, I began to ponder how feminine it felt having a penis penetrate me then being cummed on my “passable” tits. It was an incredibly sexy feeling of femininity that I’ve always dreamed of and, of course, didn’t want to end.

Yet next was my turn…

Sharon, meanwhile, had gotten up and grabbed a towel hanging from a chair and began to clean her hot milky cum off of me which I had thought was quite polite. Already cleaned off, I pull up my bustier and gave Sharon a soft kiss with a little hint that I wanted her, right then and there.

She laid down right beside me and we kissed some more, eventually with more passion as she began caressing my still-aroused cock poking visibly through my pantyhose. I let out a soft moan as Sharon then reached inside of my pantyhose to grab and lightly stroke my love rod, all the while, without even a hesitation from ramming her tongue down my throat.

She stopped and straddled me, yet again, and pulled down my pantyhose just far enough to expose my throbbing cock appropriately pointing directly at her. Like an instinct, she grabbed my love rod and began licking it like a popsicle. Then, similar to my own cock play on her, she lightly licked then sucked on the head which caused my love rod to ache since it couldn’t get any harder.

I could then see my whole cock in her mouth as she held it there for a second, giving me a sultry look. Then, back out and back in to her mouth it went as I released a high pitched shrill. Sharon sucked harder and faster, even moaning herself as I could see she was very into it, and very clearly experienced as well.

Continue to Part 3

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5 comments on “I Kissed a “Girl” and I Liked It, Part 2
  1. mariasue says:

    As I was alone at home after work I work nights in a hospital as I’m a guy as i was at work there was no one in the nurse’s lockerroom as I slip in the womens locker an search the lockers an found a pair of wht silk pantys an bra set as I slip on the bra an pantys on an the white pantyhose as i was so curious to see how women clothing felt on me as I slip on the white silk pantyhose on one foot at a time as I slip my nurse pants an smuck a lite pink outfite on as. I was wearing my asst nurses white silk pantys an bra on me plus her white silk pantyhose on my legs I could fill my legs filling silk an comfortable as I decided to slip on her pink Clogs on my feet an slip her name with mine as she was off for the next two days as she was not working I took a vantage of me trying her stuff on as. I was 3 hours in my shift she walk in to the nurses locker room with out me noticed her come in as I was at the desk as she walk up to me an said an whispered in my ear you can slip my lt pink clogs off your feet so I can see you wearing my white pantyhose an I beat you have my wht silk pantys an bra on as she said slip off my lite pink clogs an slip on my hot pink clogs on you feet as I did as she told me she told me before. I get off off work. I want you to go and get my hot pink nail polish an slip off my pantyhose an pant your nails an slip on my silk white stay-up stockings an leave my pink nurses smock an. Pants on you. An wear them home an wear them on Friday when you work with me an julie said. I wear the same outfit on friday.

  2. PantyhoseFiend says:

    Love your stories. They get me so horny and wet. Keep’em coming

  3. Sheery says:

    Thank you @PantyhoseFiend! Next part coming (excuse the pun) soon!

  4. Candi says:

    This is like my dream!!!!! This is what I really desire! I’d love to be penetrated just like you were and then to be titty fucked and have her cum all over my face, neck and tits!!!! I really dream about such a lovely and oh so sexy encounter!!!! I’m so happy for you to experience this, I really want this so to be me so badly!!!!

  5. Kim Cummings says:

    That’s what I love. The bitch was squealing now as we intensified the hot talk about how to make sure that the new sensuously beautiful and sexy baby is doing well and the taboo relationship between the two of us are in the next steps in the world of the hot willingness to be the two lesbians making it with a indefatigable spiritual growth in a frenzy of lust and the hot willingness to get it hard in a kinky sexual fun and exciting experience. We are into the lingerie and pantyhose together with high heels! I insisted on the seductive lingerie and being a receptive bitch for the two of us. We soon were engaged in a frenzy filled lust and the rest of the sensuous feeling of our own hot and sexy feminine look of your lips glistening with lip gloss, tasty as we French kiss. The shimmering pantyhose are wet and bulging. I am so excited for this hard cock in my mouth and ass. I started to get involved in a romantic relationship with the help of my favorite girl. She is very hot and sexy looking in her own lingerie and high heels! Come tell me how much you want me. It was obviously noticeable as her pantyhose was wet and bulging! I started to caress your wet panties and pantyhose together and talk naughty, I am so excited to announce that we are going to enjoy it tonight and tomorrow. The first thing that she was determined to get was a good sucking. I bring it to my mouth. …

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