SPECIAL FRIDAYS - 02
By Libnos
It was a tough week of choices for me. I had never gone such a long time without masturbating so that by the time Friday rolled around I was decidedly horny. Maybe my heightened libido was responsible for me to shave off all my body hair. I then followed it up with a treatment of Nair to remove any residual stubble before meeting Anita on Friday. I was as slick and smooth as a baby when I picked her up. It actually felt sexy and with my blue balls I was ready for anything that night.
I had previously decided that I wanted to take her out to a fancy restaurant for dinner and then we would go dancing. She accused me laughingly of using dancing to cop a cheap feel when I told her and I had to agree with her. She also told me that Belinda was over at her grandma's for the night.
When I entered her condo to pick her up that Friday evening it appeared that she had gone all out to dress and prepare herself for our evening out. She was wearing a lovely dress that hugged her beautiful figure and the mid thigh length accentuated her legs atop her four inch heels. Her hair was swept around her head in a coiffure that provided a perfect compliment to her face and together with her subtle make-up emphasized her femininity.
"Wow," I told her as I took her in my arms, "You are a vision. I feel sort of like a bumpkin next to you.
My cock went rigid as I held her soft body against mine.
" Thank you. I can tell you're pretty horny."
"You have no idea."
"Yes, I do. Its been a long week for me too."
"You abstained?"
"I couldn't ask you to not masturbate and not abstain myself."
"I'm not going to beat around the bush. I want you to know that I love you and I want you in my life."
"I love you too and we need to talk about a formal relationship soon." she responded.
"Are you going to ask me to marry you? You're daughter wants a daddy and I'm more than ready to take on that role. So when are you going to ask me?" I laughed, thinking about Belinda's request.
"When I do," she responded, "it will be a surprise."
I wondered what sort of surprise she had in mind.
That evening we dined at the best restaurant in town which also had a lounge with a dance floor and a pianist. We had wine with our dinner and then switched to our favorite beer afterward. I slipped the pianist a twenty and he played some of my favorite, slow, romantic songs. A couple of guys tried to cut in or ask her to dance but she declined to leave me and I felt like a million dollars. I had the prettiest girl in the room who wanted nobody else but me. It was a great ego booster because she was hit on by some really handsome, masculine guys.
I had a hard-on most of the evening and kept poking her with it as we danced. She delighted in pushing her pussy back at my cock so that I eventually had a wet spot from precum on the front of my pants. It was embarrassing to keep myself close behind her as we left and returned to our table. She knew what was going on and just smirked at me.
Before we had consumed too many beers we headed back to her condo. It was only about 10:30 when we got there and as we entered she took me into her bedroom and we stripped together. The sight of her in a black bra with her breasts overflowing the tops, her black thong and garter belt with black stockings was almost too much for me.
"Oh Anita. You're so sexy and beautiful. Lordee woman, you've got me turned on like no one ever has."
She ran her hand over my newly hairless chest and then slid it down to my hairless pubis.
"Lordee!!" she mimicked, "You look and feel pretty sexy yourself. Before we get into the kinky stuff I want you to do something for me. Go into the bathroom and give yourself an enema. Its all set up and do it at least twice to make yourself nice and clean down there."
I hesitated and looked at her with what must have been a puzzled look on my face.
"You do trust me don't you?"
Without responding orally, I turned and walked toward the bathroom.
"That's my girl." I heard behind me and my cock grew more erect.
When I returned ten minutes later feeling she had removed her makeup, tied back her hair and had on her boxers and a large T shirt. She was standing by the bed with her hand behind her.
"Put this on." she told me as she brought out a pretty corslet trimmed in lace from behind her back and handed it to me. I hesitated a moment before taking it in my hand and awkwardly tried to put it on.
"Here, let me help you, Simone. With a little practice you'll get the hang of it."
After she had it on wrapped around me she began to tighten it, pulling in my waist until I had developed a more feminine form. Then she brought out some imitation breast forms and stuffed them in the empty cups.
Next, she gave me a pair of white stockings and helped me put them on and attach them to the garter straps hanging from the corslet. Finally, she handed me a pair of white, satin panties trimmed with lace that I slipped on. The feel of the satiny material felt exquisite against my cock and balls. With my erection tucked up under the corslet I felt very feminine. It was strange how I was beginning to feel more comfortable dressed as a woman.
"There, you're starting to look like a real girl. Now come into the bathroom where the light is better and I'll put your make-up on."
"Make-up?"
"Yes, Simone. A girl has to have make-up on to look her best for her lover."
Even with my raging libido I was beginning to wonder if this was going too far but I followed her into the bathroom. After getting me under the brighter lights of the bathroom she went to work with lipstick, mascara, eye shade and makeup.
"Now Simone, I want you to watch what I do and the sequence I do it in so next time you can try to do it yourself. When we make love in the future on our special night, you'll want to get yourself ready for me like a real girl does for her lover."
After about twenty minutes she finished and told me to wait as she left the room. While she was gone I glanced in the mirror and was awe struck at the changes she had made on my face. My features, which before were passably masculine, were now passably feminine. As she came back I was still staring at myself in the mirror. She came back carrying a dark wig.
""What do you think Simone? I just did a fast job with the makeup but with this wig you could pass as a woman easily. Let me put this wig on and then take another look."
She carefully placed the shoulder length wig on my head and I looked back in the mirror. My god, I was a woman. My cock immediately began to throb for some reason. I was confused. I was turning myself on.
"Oh Simone, you look so good. You look so sweet, honey. There are some shoes by the bed. Why don't you put them on and see how you look in the full length mirror? I think you're feet are as small as mine but if they aren't we can get some that will fit you."
I went into the bedroom and found the shoes; a woman's shoe with 4 inch heel. Slipping them on I discovered that they were a little snug but I stood in them and looked at myself in the mirror. The heels lifted my ass and gave my legs a feminine look. My god!!, I thought. I look like some guy's wet dream as I slowly turned to look at myself.
"You're lovely Simone. Are you ready to have Andy make love to you?" She asked as she took me in her arms and gave me a passionate kiss without waiting for a response. I hungrily sucked her tongue as it probed my between my lips. Something hard probed me in the groin as she pressed into me and it felt like another cock pressing against mine. My mind was in a turmoil from her kiss, now it was utterly confused.
Breaking from me stepped back and put her hands on my shoulders and pressed down.
"I want you on your knees, Simone."
"Yes, my darling."
Falling to my knees in front of her she lifted her T shirt to reveal the head of an almost real looking cockhead sticking up above the waist band of her boxers. The large, purple head seemed grotesque against her soft belly and when she pushed the boxers down it fell forward to point directly at my mouth. The straps holding it in place at her pussy were snug around her hips and between her thighs.
As her boxers fell to her feet, she said, " Take it in your hand Simone and place the head in your mouth."
I stared at the realistic head of the cock and a feeling of revulsion came over me. It was so real looking with a slit in the end and the veins standing out on the shaft.
"I don't think I can do this, honey."
"Oh Simone, please try. I think you'll find its not too bad. I promised I would never humiliate you and this will never leave our bedroom unless you want it to. When you take it in your mouth I will show you something I think will turn you on."
I reluctantly reached up and grasped the shaft and then leaned forward and took it in my mouth. I still didn't feel right about it but I did it to please her. I closed my eyes so I wouldn't be able to see it protruding out of my mouth. It felt so soft and real laying on my mouth. Except for the coolness of the plastic I felt that it could be a real cock and I shuddered to think of my reputation if this ever got out.
"Now, tighten your lips around it and take a suction on it. Good, now hold it a second.
A sudden flash caused my eyes to pop open and I blinked as a second flash followed. I looked up and saw Anita with a digital camera pointed at me.
I fell back away from her, the dildo slipping from my lips, as I went into panic mode. My cock instantly deflating.
"What are you doing?" I squeaked out.
"Calm down. Calm down, Simone. These are for you."
"For me??"
"Now look." she told me, thrusting the camera with the small screen in front of me.
"See. No one can recognize you. I just wanted you to see how sexy you looked with a cock sticking out of your mouth. See, with your lipstick, mascara and eye shadow, you're just a woman sucking a cock. Just you and I know who it is and you look so sexy with your red lips wrapped so tightly around the shaft and your hollow cheeks as you suck on it. I want to print up a copy for you to take home when you go."
I looked at the small screen, my blood pressure and breathing returning to near normal. Reason slowly returned as I listened to her. She was right. I didn't even recognize myself. If I hadn't known it was me, I'd think it was just a picture of a woman sucking cock. But just looking at the tiny picture seemed intriguing some how.
"OK, I'll put the camera away. Just get up on the bed and watch what I do."
Getting on the bed I fell on my back and she got on with her head between my legs. She pushed the crotch of my panties aside and grasping my still soft cock she took the head in my mouth and within a few minutes of tongue and lip action, she had me hard again.
"See how easy it is to get a guy hard?" she asked.
"Why are you doing this?" I moaned.
"A girl should know how to suck cock. If you're going to be my girl, I want you to be able to do it well. It will help you feel so feminine pleasing your man. You want to please me don't you?"
"Oh yes, Andy."
"There, that's my girl. Think about your pussy. Think how it would feel so nice and full of my cock after you get it hard with your mouth."
While she was talking to me she was slowly rubbing my cock through my silky panties. God, it felt good. and I started to buck my hips against her hand. I wanted to cum so bad, but she didn't respond to my body's need. She just kept moving her hand slowly.
"Would you like me to put my hard cock in your pussy and make it nice and full?"
"Yes, oh yes, Andy. Please put your hard cock in my pussy. I want to cum so bad."
She fumbled around at the bedside table for a moment and then I felt her hand push my panties aside again and a finger covered with some sort of cool grease pressed into my ass. I jumped at the invasion and she reassured me as I felt her finger reached my prostate and begin to rub it gently.
"Oh Andy!" I moaned. "That feels so good."
I groaned in frustration as she suddenly withdrew her finger from my ass and then pushed my knees up so that my ass was fully exposed. I felt the head of her dildo press against my ass..
"Just relax now Simone. Let my big hard cock fill you up."
She kept pressing and the pain began to build up. Just when I thought I'd have to stop her the head slipped inside and the pain eased off. She then continued working it inside me. First in short little strokes that took it a little deeper each time and then as she got in deep she shifted to longer strokes. My pleasure began to grow as the pain eased and soon she was plunging into me.
"Does your pussy feel full now Simone?
"Oh yes! Oh yes! That feels so good! Don't stop.! Don't stop!"
I was hers. She claimed me like a man would a woman. A million feelings were pulsing through my body that seemed to be centered in my groin. I was on fire for my lover. I wanted him in me. I wanted to pleasure him and take his cum. How quickly I was switching the role I'd assumed was mine.
He was beginning to pant as he fucked me. I felt so good knowing I was pleasuring him as he was pleasuring me. An orgasm was beginning to build in my groin, even though my clitty was not being manipulated. We both burst forth in what seemed a roar of sound and emotion as my cum flooded my panties. This was one of the best cums I'd ever experienced and I wrapped my arms up around her body as our lips mashed together in a final passionate kiss. The ecstacy of our mutual cum slowly ebbed away and she slid the dildo out of my body. Unstrapping it she tossed it in the corner and then flopped down on the bed beside me. I rolled over and looked down at her face and gently kissed her soft lips.
"Thank you, my darling. I never knew what it felt to be a woman before. It was glorious."
"You're welcome, lover. I do love being Andy and I'm so glad you're happy being Simone." She giggled and told me, "You're lipstick is smeared and your wig is on crooked. As a girl you should keep up appearances."
"Never mind Andy. You've got lipstick all over your face so I suggest we go for a shower. After that I think I'll go home before I fall asleep. This has been one helluva night."
We undressed and went into shower together. While were there with the water cascading around us she gave me a blow job and shared the cum with me in a long kiss. The cum coated my mouth and reminded me for some time what had transpired that evening. Before I left she printed off the pictures of me blowing her cock to take with me. I felt so drained and happy and I slept like a log back at my place until late in the morning.
Waking, I recalled what had happened the night before and realized she'd taken me on a new step in our relationship. However, I didn't feel any misgivings. I felt so in love with her and felt I could trust her completely. Looking at the pictures she had given me my cock got hard again. I didn't know whether it was because it was an erotic picture of a woman sucking a cock or knowing that it was me.
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To be continued