Larry / Lynnette




Donna M.



I had a date!

I’m Larry.  My wife, Doreen has tolerated my desires to dress as a woman—be a woman, actually—but going out dressed as I wanted to instead of just around the house was to be the experience of a lifetime.  Maurice was a new acquaintance who knew my inclinations and actually asked me out as ‘Lynnette.’  He was a big gorgeous man who readily admitted to being bisexual.  He understood that for our date I was all female.

He’d made reservations at a great restaurant.  I shaved meticulously all over and wore the sexiest white satin panties I owned.  The padded bra looked nice under the special navy and clingy cocktail dress that accentuated my legs, nicely encased within sexy white hosiery.  I decided on the blond wig tonight and slowly examined myself in the bedroom mirror, turning this way and that to study how I looked, before stepping into my heels.

Good enough to eat, I thought, as a shiver of anticipation went through me.

Maurice picked me up and I loved the way his eyes grew wide as he looked at me.  He whispered, “Damn, you’re hot,” careful not to let my wife hear him since he didn’t fully know my situation.

I felt the tingle from his words and stare.  Yes, I felt ‘hot.’

He opened the car door for me like the gentleman he was and soon we were seated in the restaurant and ordering dinner.  He asked me if I’d paid attention to the looks I received from a couple of men.  “Of course I had” I said, emboldened by their stares; they weren’t looks of disdain, they were looks of lust.  I leaked a little I was so aroused.

Dinner was marvelous.  We went to a lounge afterwards and danced for a while.  I felt so sexy the way he held me in his strong arms as we danced cheek-to-cheek.  I also felt his bulge as he pressed against me.  I am a virgin, and so I can’t escape the trepidation of feeling his swelling manhood and thinking of what my first time will be like, especially if he is as big as he seems to be.  At the conclusion of our last dance he kissed me.  His tongue probed for mine and I melted in his arms.

We went to his apartment where we kissed again.  His hand was up under the hem of my dress and caressing an ass cheek over my panties.  I was leaking again, and soon he’d find out.  But not yet. 

I helped him undress in his bedroom and when I pulled down his boxers his cock sprung up to greet me.  As a good woman would do, I had him sit on the bed and then I knelt between his legs.  This was another new experience but one I fantasized about often and I was ready.  I took him between my lipstick coated lips and slid him into my mouth.  I was hard myself as I felt him stiffen more as I sucked him.  I didn’t do it for long since I wasn’t ready to have a man cum in my mouth.

“Are you…ready?” he tentatively asked.

I whispered that I was.

He pulled the dress up and off over my head leaving me still in bra, panties, hose and heels.  I felt like a woman more than ever and imagined my pre-cum was instead dribbling pussy juice.  Maurice was sensitive to my needs.  He put on a condom and lubed it up, and when I glanced at the size of his erection new worries arose.  Would it hurt?  I would soon find out, and no longer be a virgin.

Maurice positioned me before the big mirror and stood behind me.  He then slid my panties down slowly to my ankles and then I kicked them aside.  Holding me with his strong, masculine hands he whispered, “This is going to be nice,” most likely not realizing that he was about to take my virginity.  I bent forward slightly and opened my legs a bit as he positioned his erection at my anus and pushed it in.  The shock was amazing but not altogether unpleasant.  I gazed at our reflection and lost myself in the act.  This is what I wanted—a strong man was making love to me, and I felt so naturally feminine.

He held me at the hips as he fucked me.  Glued to our reflection I let my eyes become windows to our impending orgasms.  I felt him deep inside me, striking my prostate on each thrust and exciting my cock, which was bouncing like a taut spring to match each of his deep penetrations.

I lost track of time but eventually he groaned, “I’m going to cum, Lynnette.”

Was it the use of my special name, or the sight of his beautiful masculine body behind me reflected in the mirror, or that final thrust and its accompanying throb as he ejaculated that did it for me?  Regardless of the trigger, without a single touch I came in several ropes all over the bureau in front of me.  I groaned too.

After he slid out of me I turned to him and asked seductively, “Did you enjoy me?”

He responded with a big “Yes” and complimented me on my looks and participation.  My desire was to be accepted as a lady and he did.  I peeled the condom from his cock and complimented him in return on how full of spent semen it was.  He saw my cum all over his furniture and carpet and said, “I was going to ask you about your pleasure but I see you had a good orgasm too.”

“You, strong and handsome man, can do it to me any time you want.”

“You mean that, Lynnette?”

I told him that indeed I meant it.  We kissed again, and as we did I had an idea.  Our sex life now was nonexistent, but I wondered how my wife thought of Maurice and whether she’d be interested.  I was breathless by the time the kiss ended so I needed a few seconds before I could ask.

“How would you like a threesome, Maurice?  Maybe I could interest my wife.  Does that sound like something you’d go for?”

“Whew…Doreen is a great looking woman, and I guess she’s okay with you…you know…being Lynnette and all.  Yeah, I think that would be hot, if you think she’d go for it.”

“It won’t hurt to ask,” I said.

As he drove me home I pondered how I’d approach the question.  Maybe she and Maurice could go out on their date first before we did anything?

Regardless, I needed to shop for some nice things—maybe black undergarments this time since I’m no longer a virgin.


Donna M.


© 2016


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