She went back through the bathroom door as I went to the bed and lay down on my back. Everything seemed so good right from the comfortable feel of my wig down to the perfectly fitting heels on my feet. I looked down between my tits, over my flat crotch and down my silky legs. It looked great as well as feeling great. It made me long all the more to stay like this.
"All right lady, are you ready?" I looked over and gasped as Jan marched right over to the bed. She was still naked except for a pink cock jutting out from her twat. She sat down beside me, placed my hand on her cock, leaned down and kissed me. God, what a woman (or man). The cock was soft to the touch and fairly rigid, like she had a hard on.
"We wouldn't want Ralph to be disappointed by having a virgin ass, now would we?" She smiled again and reached down to pull my 'V' down and off. My cock sprung right up. "I'm glad he's still alive and well," she smirked.
She spread my legs and kneeled between them, obviously surveying my tits and cock with a great deal of satisfaction. She bent over, kissed my cock and then placed her arms under my legs and lifted them while spreading them wider. She then pushed them back so my ass raised up and she could see directly into my hole. "There now, you can hold them back while I go to work."
I grasped my knees and held them there wondering just how much this was going to hurt. She then reached down and got a tube of something that I hadn't even noticed when she came in. "This will make everything easier, Hon. Just let me spread this where it's needed and away we go."
She then proceeded to anoint the tip of the extension emanating from her crotch with a large gob of what appeared to be a clear, thick solution. "Just to provide maximum ease we'll just add a little here too", she muttered as the tube disappeared from sight and I felt a cold gob of something making its way around and slightly into my asshole.
I was breathing heavily by this time in anticipation of what I didn't know. Looking down through the valley of my heaving tits and past my excited cock, not to mention my loose front garters (and rear ones tight against my ass) I saw her withdraw the tube, set it aside and grasp her 'cock' just like a guy would.
Her eyes gleamed as she said "Are you ready lover?" With that she started slowly forward and I tensed myself for whatever was to come "Relax, as best you can. I'll be slow and easy."
Her hands gently pulled my cheeks apart exposing my asshole and I felt the smooth, greasy head pause at my hole. All of a sudden I felt relaxed as I just knew Jan would treat me right. Slowly the head stretched the hole as far as it needed to and then the whole knob was in. She eased it in a little further and stopped. "Let's just wait there a moment while you get adjusted.
How are you doing?"
"Just great. It's difficult to keep from squeezing on it though."
"MMMM, that'll make the owner of a real cock happy. That's what they live for. You know - like when you were fucking me - couldn't you feel it when I squeezed my twat while you were in there"?
"That's right. I just didn't make the comparison I guess." With that she eased on in until I thought the thing was going to come up my throat. I could feel her stomach and top of her thighs against my ass so she had to be in all the way.
She then began a series of slow movement in and nearly out and then back in. With each movement I began to groan louder and to thrust my ass forward on her in strokes. I let my legs come to rest on her shoulders and used my long arms and hands to reach behind her and pull her ass into me.
The feeling was marvelous and as we continued she quickened her thrust and withdrawal as I did my ass thrust. I was groaning now and just begging her "Fuck me Jan, fuck, fuck me harder!' Her body was now slapping into me with each thrust and finally my cock just had to let loose. I stayed with my body arched as my cum spewed forth all over my belly and even my lower chest.
Upon seeing this she eased right out and first thing I knew there she was, sucking the remainder cum out of my cock. Without waiting after it was dry she proceeded to lick my entire torso as if she was dying of thirst.
When she finally had me licked clean she eased herself on up so her gorgeous tits rested on mine and we kissed, and kissed and then kissed some more. She was truly wonderful as we just sucked the life out of each other. The taste of my own cum made it that much better. My ankles locked together as I wrapped my legs around her.
Finally she eased off and looked down at me. "You are the best Ronnie, the VERY best. You pass with flying colors. I can't believe a threesome with Ralph could be any better - but it'll sure be fun to try, won't it?"
We fell asleep in each others arms and stayed that way for at least two hours. Upon waking up Jan got a warm, wet cloth from the bathroom and cleaned me up where my cum had landed. She then retreated to her bedroom after telling me to put my 'V' back on.
I did so and was again admiring myself in the mirror when she returned with what appeared to be some clothes and a small velvet covered box. "We've gone this far so may as well let you see what it's like to complete your dress up.
Here, hon, slip this sweater over your head for a start."
I easily slipped it on and pulled it down over my tits (I really liked the expression 'my' tits). It came down to just below my waist as I gazed in awe at how lovely it exposed my tits. It had a v-neck and was sleeveless with the over the shoulder portion just wide enough to hide my bra straps. It was white and lent a kind of mystery as my black bra was faintly discernable beneath it.
"Ok Ms. Wonderful, let's try a skirt." With that she handed me a dark gray skirt which had a stretch waist. "Since you don't have a petticoat on you can pull it up rather than take it over your head." she said. I glance at her and she seemed very proud of her 'project'.
I stepped into the skirt and tugged it up over my hips. It was very snug as I pulled up the side zipper and buttoned it at the top. I glanced down and was pleased to see it was flat over my stomach and looked perfectly seemless on down over my crotch. The bottom of the skirt came to just above my knees and had slits on each side. My nylon clad legs extended down into my spikes - which I had not even removed during our recent 'session.'
I began to walk around and found I had to shorten my step because of the restrictions of the skirt which was practically molded to my body. 'This would not be a problem', I thought. The real neat part was the feel of the skirts' silky lining massaging my legs as I walked. Yummmmm!
"You look great but let's make you look greater. Sit down and we'll see what we can do." With that Jan brought out the velvet case and opened to expose a variety of jewelry. First thing I knew I had a gold pendant around my neck, bracelets on each wrist and a couple of rings on each hand. "Ok, stand up and let's see," she said, already standing back and admiring her handiwork.
This time as I pirouetted in front of the mirror I just knew I had to develop a plan to look like this all the time. "Jan, honey, would you please take a couple of pictures of me?" I handed her my camera and stepped away.
"Not until we comb your hair and freshen up your lipstick. My goodness you must have been doing some wild things to get them looking like that." We both laughed and I took a comb to my hair - wig. "Use this pad to clean up the smears and then you apply a fresh coat yourself." I did and it seemed like the most natural thing to do.
A couple of minutes later Jan had directed me in how to pose and we had three polaroids that really turned out great. "I can't believe that's me," I sighed. "It is you, hon, and I'm not sure even then that they do you justice," she countered.
"Thank you so much, Jan," I said as I put my arms around her and we just stood there hugging each other and sobbing away like crazy. It must have looked strange, me dressed to kill and Jan stark naked.
"Time's up - for now," she said as we broke our embrace. "I want you to know that all these clothes and jewelry were on my 'disposal' list. I want you to have them along with a few other things I'll bring in," she said as she retreated to her bedroom. I just gaped at her in wonder, not knowing what to even say.
I began to carefully strip and enjoyed every second of it. I got out my large suitcase and carefully folded each item before tenderly placing it inside. Jan returned and handed me a handful of things including two sheer nighties, a couple of bra and panty sets and another pair of spike heels. By this time I was standing there clad only in my 'V'. She took one admiring look at me and said "later" as she left the room.
Chapter 4
I groggily shook my head as I kind of semi woke up in the rest stop. One glance at my watch told me I still had plenty of time so I just closed my eyes again.
------------- Time went by quickly and I began to wonder if Ralph, Jan and I were ever going to get together. Jan had told me Ralph was out of town on a business trip and not to worry.
I continued my pornographic tour of the internet and picked up on an email conversation I had been having with 'Ellie' who lived in Las Vegas. I wasn't positive but I kind of guessed that Ellie just might be a she-male. She(?) said so many things that just struck home with me and made me quite comfortable in talking to her.
I had explained to her just how I felt about sex and the depth of my inclination to 'dressing'. I could sense the eagerness in her words when she responded to that email. It sounded just about pleading as she expressed a desire to see a picture of me. She even sent me a picture showing her fully dressed and very attractive. She had dark hair and a lovely figure - a little heavier than I am but attractive none-the-less.
After considerable thought I said 'what the hell' and I sent her a picture that Jan had taken of me fully dressed. I was somewhat concerned as to what her reaction would be but was really pleased when she mailed back with really neat compliments and a wish that we could see each other. She also commented that she would love to see just what was under those lovely clothes!
That got me and I really agonized over that. What if this was all bogus and my pics turned up in a magazine or something like that? Since I didn't respond for a couple of days she emailed again and was concerned that I might be afraid of just that. She then told me that she was a she male and ran a 'business' from her home. She promised me our correspondence would remain confidential. To emphasize this she even sent me a picture of herself naked.
I couldn't help but get excited as I looked over the picture. She had a lovely build and her hair framed a gorgeous face. Her tits looked firm and inviting - I would guess about a C cup. Her flat stomach and great hips then gave way to her cock. She was cut and appeared about 6 inches when soft. She had shaved all around it and there wasn't a hair in sight other than on her head.
All in all, she was marvelous and I couldn't help but feel envious as I looked at her tits and then her cock. I found I couldn't resist and I got out a picture I had taken of myself, naked, no make-up or wig and full height. I preceded the pic by apologizing for having a flat male chest and not knowing what to do about that.
Her response just blew me away. She told me my figure was wonderful and, with the proper handling could pass for a female anytime. Then she threw the hooker at me. She said since I loved sex, as I had previously mentioned, and had such a great figure and face she would love to have me visit her in Vegas. She had a house she owned where men came occasionally to visit her and her roommates. It was quite lucrative and she would love to have me stay with her and see what I thought of things.
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