Old Friends Ch. 02

bythe_one_who_got_away©

I came right as the words came out of her mouth, and almost cut my dick off zipping up my slacks. I managed dumbly to mumble, "I wanted to surprise you, I made reservations for seven."

Emily walked past me to go to her bathroom, still completely naked, swishing her hips like a cat in heat as she said over her shoulder, "I'll be ready in fifteen. Want me to meet you in the garage."

I could only nod and ask, "Which car would you like to take?"

She stopped and thought for a second and asked, "Can we take the Jag?" I could only nod my agreement. Then she looked back at my crotch and said, "You might want to change you came on your slacks Mikey."

I was changed and cleaned up wearing a pair of tight blue jeans and a vintage t-shirt with my hair down, being as it was a more-than-casual atmosphere at the restaurant, when I walked in to the garage and saw her sitting in my '56 Jag roadster, "I thought you wanted to take the new one. I haven't had this one outside since it came back from the restorers."

"Oh Mikey stop being such a bore, anyway its to hot tonight not to take advantage of the convertible."

"I have three convertibles in here, why do we have to take this one?" I replied, "Because if you don't we'll be late for your reservation." I had to admit she was right, we only had twenty-five minutes to get there and I hadn't even gotten to test-drive the newest edition to my collection since it had come back from being restored. Why not I said to my self before saying aloud, "you win, buckle up. I'm going to have to skin it back a little to get there on time."

When she smiled after I told her to buckle up, I realized that I was still secretly in love with this woman from my past, and knew then that no matter how much I haggled and argued with her she would always ended up getting exactly what she wanted from me, just like it was back in college.

I was nervous the entire night, but she just went on like always as if her 'show' had never even happened. We ate our meal, after which we had a few drinks at the bar before heading back to the house. Both of us were a little drunk when we stumbled, giggling back into my library, were I kept my personal wet bar, deciding to have a few more drinks before we went to bed.

I poured us both a double of aged single malt whiskey, and we both took a drink, before she made a face a the strength of the 100 proof liquor and said, "Goddamn Mickey I never could see how you could drink this shit." I replied, "It's definitely an acquired taste, but it gets the job done."

We then finished our drinks and headed of to our separate bedrooms. I was having a restless sleep, like most nights, but tonight was different, in the fact that, instead of worries from the office keeping me awake, it was the mental picture I had of Emily riding her dildo. I finally dosed off around two-thirty in the morning to a fitful sleep. At first I wasn't sure what woke me around four that morning, but then I realized it was just Emily climbing into bed with me, which wasn't a surprise in itself, as she has been doing that since I've known her, but tonight I quickly found out what felt so different. Emily wasn't wearing the t-shirt and boys-briefs that she usually wore to bed, in fact I was pretty sure she wasn't wearing anything at all.

As all of this was registering in my sleep-fogged brain, she quickly kissed me deeper and harder than I had ever been kissed in my entire life. I quickly pushed her away and said, "Emma we shouldn't be doing this where friends. I don't like to fuck my friends, it always causes complications." She rung my jaw with her fist an said in a stern voice, "I don't want to her any of your crap, Linda. I've noticed how sorry Mickey is and I'm her to make it better, and your not going to fuck me, I'm about to fuck you. Now go in my bathroom and fix yourself up, Linda, you look like shit. You'll find my instructions for you on the toilet."

It was then that I noticed she was wearing her pink dong in a strap-on harness. I didn't argue, I knew that I wouldn't be able to talk her out of it. Then it hit me that she had not called me Mickey like usual, but in fact had called me Linda. Linda was the name my sisters use when they would play dress up with their little brother when I was little, Emily was one of the few people who knew about my cross-dressing adventures in early child-hood.

I found myself getting kind of aroused as I walked down the hall to Emily's bathroom wondering just what hear instructions were going to be. When I got there it was all to clear what she wanted, but I read the note anyway. I was to shave all my body hair and the goatee, that masked the feminine lines to my jaw, fix my hair into a more girly style, put on make-up, which she had picked out for me, put on a blue bra and thong set, she even had a pair of breast forms laid out for me, and then put on her only evening dress, a beautiful blue number that she had bought shortly after moving in, and panty-hose, she also had managed to purchase a pair of blue heels in my size.

When I was finished, all I could do was sit there and stare at my reflection in the stand mirror on the door. With the breast forms and the make-up, she picked out a hooker-red lipstick and green eye-shadow, along with the foundation and rouge, I must admit I wouldn't have recognize the beautiful woman staring back at me in the mirror, if I hadn't known that it was me in the dress.

So made up and looking more like a women than the man that I was I walked back to my room, taking great care not to lose my balance in the heels. When I walked through the door Emily wolf-whistled at me and I felt myself blush ant the praise.

She quickly crossed the carpet and then surprised me when she whispered, "Gods, Linda, your beautiful." Before pulling me into a slow, gentle kiss. She lightly nibbled on my lower lip before she slowly parted them with her tongue. We kissed for what seemed like ages before she finally broke the embrace to stare at me critically, her eyes roamed to my crotch before she said, "Well, Linda, we just can't have that, it make my beautiful girlfriend look like a man in drag."

After saying this she immediately lifted the hem of the dress that I was wearing and began sucking me of in true fervor. I was already extremely aroused by this point so I didn't take long at all for me to blow my load, and she swallowed every drop.

"Now that you have got yours, Linda, don't you think it's time for me to get mine?" this was the part that I was dreading, but at this point she was in complete control, and even though I am normally the one who's always in charge, in a way it strangely felt right letting her take control like this so I just nodded. Then she said, "I can tell your going to be a very good girl aren't you, why don't you show me how good you are and bend over the side of the bed?"

And I did it, I didn't even think, she commanded and I obeyed. Before to long I felt her slap my panty-clad ass with enough force that it would've knocked me over had I not been leaning on the bed, I whimpered and chanced a look over my shoulder, noticing she was now rubbing lube onto that plastic cock, as if she was jacking-off, which brought me another raging wood before she finished and pulled the panties down off my ass.

As she put the tip of her dildo to my ass I tensed out of instinct, as she bent over and whispered into my ear, "Just relax sweetie and you'll enjoy this more than I will." I forced myself to relax my sphincter as she slipped the dildo, I had witnessed her using on herself just hours earlier, all the way into my ass. At first it hurt like hell, but she just stood there taking my inexperience into consideration.

Soon as the pain began to subside she brought her cock all the way back out of my ass with the head resting on my rose bud. I felt strangely empty without it, and remember wishing she would put it back, and started to push back against it. She entered me again and began fucking me with a slow rhythm, and the feel of her dick in my ass and my dick rubbing against the satin sheets covering my feather bed was beginning to drive me nuts. She gave a soft moan as she placed her hand on my hips and starting to fuck me in honest.

It was driving me wild with passion I knew I wouldn't last much longer, and by the increasing pitch and intensity of her moans, I knew she wouldn't either. I began bucking back to meet her, and as I did this she started fucking me with a new kind of intensity. It was only about two more stokes before I had the most intense orgasm of my life. She felt when I came and pulled out of my ass, dropping the strap-on harness to her ankle before lying on my bed and shoving her dripping cunt into my face saying breathlessly, "now finish momma off and make her cum like a good little slut." and was grinding my face with her pussy before she had the sentence out of her mouth.

I lapped the juices off her cunt, like man eating his last meal. She was already screaming in ecstasy well before I took the nub off her clit into my mouth, sucking her off with all I had, before bringing her to a mountainous orgasm that gushed what of her juices I couldn't catch in my mouth onto my hookerish face.

I knew then that thing would never be the same in my house from that point on, and was surprised that I was strangely enjoying myself more than I had in years. I felt complete lying there naked, painted up like a prostitute beside Emily, who was sleeping like an angel.

To Be Continued.

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