After that wild evening, when she'd dressed me as a woman for the first time, I awoke the next morning without any misgivings or concerns. I trusted her and we and felt comfortable that would continue our relationship in the same direction but with mutual love and respect. Looking at the pictures she'd taken and printed off for me I immediately got a hard-on. I wasn't sure it was because it was because I knew it was me or just a picture of a woman sucking on a cock.
Calling her shortly after some brunch, we decided to meet and make Saturday a family day with Belinda and Anita's mother. I had the biggest car so we decided I would pick them up and go to the beach that afternoon. At the beach I saw Anita in a bikini for the first time. I'd seen her naked but to see her in public with bits of cloth barely covering the strategic parts of her body was even more erotic for some reason. I knew that if it hadn't appeared that we were a family she would have been hit on many times. She had a fabulous body and I felt really proud that the world saw her as my woman. Since she was a cop I wasn't worried that she couldn't handle any guy that got out of line anyway. I'd seen her off duty, snub nosed 38 in her beach bag and she knew how to use it. It made my groin tingle when I thought how I could be dependent on her for my protection. I thought how nice it would be if I could wear a bikini and look like she did. It felt strange to associate myself with womanhood, but now, whenever I did, my cock would harden.
We covered Belinda with lots of spf 30 sun screen, since being a red-head she could be more sensitive to UV radiation in the sunshine. Then, we all put some on. Belinda and I built sand castles with her toy shovel and bucket while Anita and her mother sunned themselves. I really enjoyed bonding with the little girl. After that we all went for a long walk up the beach and played in the surf until it was time to go home. Belinda held my hand the whole time. It was so easy to give my heart to this little girl, just like I did with her mother.
We stopped at a Burger King on the way home and had our dinner. Anita insisted on buying. I wasn't worried about it not being a guy thing since she probably made a good salary and supported herself and Belinda. Arriving back home we dropped Anita's mom off at home and then went over to the condo pool and had a brief dip to wash the salt off our bodies. Next we went to Anita's condo and changed our clothes. Then we watched TV until Belinda tired and we both put her to bed. Afterward we went into Anita's room and made slow, passionate love. She wanted me on top. I was thinking all the time about my experience as a woman the night before and it kept me hard through three orgasms. Later, we rested on the bed before I went home.
"You were really hot tonight lover. Any reason for it?"
"I'm not sure whether it was the memory of you in that bikini today, our hairless bodies or our session last night." I responded.
"I take it you liked our session last night."
"Very much. I honestly felt so feminine submitting to you. I'm almost afraid to tell you how much it turned me on."
"Why would you be afraid to tell me? I know you were turned on. You came when I fucked your pussy didn't you?"
"Yes, I came but I don't know how far you want to take me into femininity and all that it could mean."
"Let me tell you right now that I want you to trust me that I will not jeopardize any future relationship we might have by making you do something you feel uncomfortable with. Does that satisfy you?"
"Somewhat, but I'm not sure how far I might take myself if my libido is raging."
"OK then, I will promise to keep you under control. Our future relationship must include Belinda and I'm becoming very sure that I want you as her daddy. A daddy has to be masculine, not feminine. So, I have a very big reason to keep things under control by keeping our special love making to Friday nights. At least, " she continued, "until she's old enough to understand."
"Do you think you will want me to suck a real cock someday?"
"I don't want to lose my respect for you as a man or feel I've humiliated you. My plans only require that you submit to me sexually on our special Fridays and to get you to enjoy being a woman at those times. Do you think you might want to suck a real man's cock someday? A woman will do that for her man."
"I don't think I could do that, but as I said, my libido might drive me to do it if it would pleasure you to see me do it. Maybe as a woman I could."
"That's so lovely, sweetheart. I just love it when you submit to me, but I want to pleasure you too. That's why our Fridays are so special. I think about it all week, don't you?"
"Yes, especially when I don't masturbate. I try to not to think about you and our special Friday sessions during the week and now those pictures have me climbing the walls."
"That's the way I want my girl and my guy." She giggled. "Hot to trot and ready to try anything."
I groaned in response, "You're an evil influence, dear heart." I told her as I kissed her softly on the lips.
She responded tenderly to my kiss and then told me, "I want you ready for next Friday night so get your enema and shaving taken care of before you get here. Also, I want you to think about permanent hair removal with lasers. A lot of guys are doing that now."
"I've heard about it. Is it expensive?"
"Somewhat, I understand, but when you balance it against never having to shave again, how it feels and how sexy it will make you look I believe it's worth it."
"I'll get some quotes and think about it."
"Thank you sweetheart. Now it's time for you to get going. Why don't you plan on coming for dinner on Tuesday?"
"I'd like that. Thank you."
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So my integration into a family situation with Anita and Belinda continued as did my slow transition into enjoying submitting to Andy and being his woman on our special Fridays. I found over time that my "pussy" became my main way to achieve an orgasm at those times and I yearned more and more for her "cock" My training as a "cocksucker" with the dildo continued also. I learned to deepthroat it and for some reason this gave me a feeling of deep satisfaction, especially after she went to a larger size. She also began to use it in my pussy and I was quickly able to take it and grow accustomed to the larger size and the additional fullness it provided. The orgasms I had with it were much more intense and satisfying also. We began to incorporate erotic DVDs dealing with transgendered males into our special Friday evening bedroom romps and my libido soared in conjunction with my need to submit. I had a feeling that she was building me up for something and I didn't know whether I wanted to proceed in ignorance or confront her on what she was planning. Eventually, I just let her go ahead as I was really enjoying the eroticism of my seduction and wondering how far she would take me. I knew I loved her and had to trust her. Except for our special Friday nights our love life was a pattern of normal love and interaction between a man and woman. However, I really looked forward to Friday.
After checking prices I began a series of laser hair removal procedures and within a month my whole body was bare and hair free except for the top of my head. Anita also convinced me to let them thin my eyebrows somewhat. I was afraid it would give me a more feminine look but it didn't appear to be too feminine when they were through..
My exploration of dressing in women's clothes and applying makeup proceeded in parallel with my other activities and I slowly learned the things that women seemed to grow up knowing. "How to make themselves attractive to men." Anita insisted I do it with that in mind. My sensuality as a woman increased and I developed feminine traits as I walked, sat, conversed and even ate. My comfort level as a woman grew and I was starting to move out of the bedroom and into the condo in my new persona while Belinda was asleep.
One Friday evening after dressing and watching a particularly hot, erotic DVD Andy asked me if I wanted to go for a walk.
"Go for a walk? Where to?" I responded nervously.
"Just a walk together on a warm summer evening."
"You've got to be kidding. I didn't think that I would be leaving the confines of your condo as a woman."
"I just want to show you that for all intents and purposes you are a woman and you could easily pass for one."
I wanted to confront her but another side of me, pushed by my libido, couldn't say no so I allowed her to lead me out the door to the sidewalk. I was scared but it was dark and I could feel my cock urging me on. It was trapped in a male thong that kept it confined and tight to my body and struggled to get free.
"C'mon." Get up she told me as she took my hand and pulled me up out of my chair.
Reluctantly, I rose and allowed her to lead me toward the door.
"I don't think this is a good idea." I told her but allowed her to lead me outside. Andy was dressed in a pair of oversize men's shorts, running shoes and a bulky sweat shirt. Her hair was pulled back under a baseball cap and without makeup she looked a little masculine but somewhat dykish. This was confirmed a few minutes later as we passed another couple out walking in the dark condo complex and I heard a whispered "lesbians" between them.
Anita must have heard it too because she giggled and whispered to me. "See, you passed. They think we're both lesbians."
"Oh great!" I responded and rolled back my eyes in mock disgust.
We continued walking and I found that my hips rolled a little with the high heels on much to the delight of Andy. We passed a group of guys sitting out on a patio drinking beer and were rewarded with a few catcalls.
"Why don't you girls come over here and we'll show you why men make better lovers." one called out to our mutual embarrassment and we hurried away giggling and listening to the laughter behind us.
When we arrived back at Andy's condo I found I wasn't as nervous as when we'd started but wondered if I would pass as a woman in the daylight or under lights.
"There, that wasn't too bad was it. Nobody took you for a guy."
"It's OK in the dark but I probably wouldn't pass in the daylight."
"How much do you want to bet?"
"What do you mean?"
"How much or what do you want to bet that you wouldn't pass as a woman? Hell, you're a betterilooking woman than some of the women I meet on the job every day. I'll tell you what, if you don't pass as a woman I'll do anything you want and if you pass you'll do everything I want. How about it?"
"This sounds like a setup."
"It is and it's a sure thing for me so you'd better be ready to pay up."
"What am I going to have to do?" I asked with a tingling now in my groin as we continued to stand outside her front door.
"I'll tell you that when I prove to you that you can easily pass as a woman... Are you ready to do it?"
"Now?"
"I can't think of a better time. Let me go in and get my wallet and car keys and I'll get you a purse."
I was stunned and suddenly apprehensive. How did I get myself into this mess?
She was back quickly and handed me a purse as she led me to her car.
"I put your wallet in the purse. We're going to the store."
"What am I going to do there?"
"Here's a list of things I need. You're going to go in and buy them for me."
"You're not going with me?"
"No, you don't need me. Just go in to Albertson's and do it."
What had I gotten myself into? I was in a panic. In a few minutes she's pulled into the parking lot.
"OK. Go ahead. Get me the stuff on the list. I only ask you to remember that when we make love on Fridays, you're a woman. Go in there and be a woman. Don't look anyone in the eye, especially men."
Apprehensively, I opened the car door and got out. I was so scared I didn't think my legs would hold me.
"Go ahead." she urged. "Remember, you're a woman. Be one." she commanded.
"Yes, my darling." I whispered as I gathered my nerve and began to move toward the door and bright lights of the store.
I passed a couple coming out but they just glanced at me to avoid hitting me with their cart and I breathed a sigh of relief as I breezed by them. The automatic doors opened as I approached and I was inside under the bright lights. I realized that if I looked nervous or hesitated it would draw attention to me so I grabbed a cart and started down the nearest aisle trying to keep up a leisurely pace without drawing attention to myself. I was thankful the store was not busy as I strolled up and down the aisles picking up items on the list. If I met anyone I would pretend to be studying the list to avoid looking at them. At first I was so tense that my mind seemed to be nonfunctional and I had a hard time thinking. When I'd been in the store for about fifteen minutes without being discovered I began to relax and I remembered to swing my hips as I walked. I even smiled at a young couple with a small child and they smiled back.
I was doing it. I was a woman. Somehow, my cock began to stir in its tight nest and when I got to the check out I responded to the cashier's greeting with a higher pitched response and a smile. I paid after rummaging in my purse and finding my wallet, said "Thank you" to the cashier in my pseudo feminine voice and then left the store feeling very pleased with myself. Andy was waiting for me in the car.
"How did it go?" she asked after depositing the groceries I the back of her small SUV and getting back into the passenger seat.
"I think it went very well." I responded as I relaxed in the seat with a sigh.
"Does that mean I won the bet?" she asked as we returned back to her condo..
I guess it does. What are you going to want me to do?"
"I'll tell you when we get back to my place. You aren't going to be afraid to go out anymore are you?"
"Well, I think I'm always going to be a little apprehensive. I guess it will be like stage fright. You never get rid of it entirely."
++++++++++++++++++++++++++++++++
When we got back to Andy's condo I helped him carry in some of the groceries and sat at the kitchen table watching him put them away.
When she finished he got us both a beer and we adjourned to the living room. He patted the seat next to him and I sat close with our thighs touching. Raising his bottle me he congratulated me.
"Here's to you Simone for the wonderful job you did in you're 'coming out.'"
I responded by first kissing him lightly on the lips and then raised my bottle, touched his and responded in my very best contralto voice,
"Thank you. Now, what am I going to have to do to pay off the bet?"
"I have another first for you in mind."
Taking my hand he looked me in the eye.
"I want you to suck a real cock."
I was stunned and took a hefty swallow of the beer before responding.
"I don't think I could do that, my darling." I choked back. "I'm afraid you would lose all respect for me and I find it repulsive."
"I would make it as easy for you as possible, but if our relationship is to proceed I need you to do this for me."
"Why?"
"It would be almost the ultimate in control over you for me that you would submit to a real man and it would be a big turn-on. For yourself, you'd be a woman submitting to a man.
I thought about it for a few minutes without saying anything. I'd occasionally wondered what it would be like to take another guys cock in my mouth but had never done anything about it. I guess I wasn't that curious. Maybe as a woman I could satisfy my curiosity if Anita wouldn't lose her respect for me. I had to ask her.
"Maybe Andy wouldn't lose his respect for me, but what about Anita?"
"I believe I can speak for Anita when I tell you that she's OK with it.. What happens on our Friday nights is just between us anyway. I want to keep it that way. Now I want to make love to the sweetest girl in the whole world."
He put his arms around me and brought his lips to mine in an open mouth kiss that I quickly responded to. When we finally broke for air he took me by the hand and we went into the bedroom. Quickly undressing, except for my thigh high stockings, I lay on the bed and Andy slipped his naked body between my legs and began to kiss and suckle on my nipples. These were the times I wished I had real breasts to give him but my nipples had gained some sensitivity since we'd been going together so I enjoyed his ministrations. Finally, he slid up my body and brought his lips near my ear.
"I want to go deep inside you Simone. I want you to be my slut bitch. I want to put my cum deep inside you."
I moaned in response as Andy's cock slipped inside me. I wrapped my legs around him and locked my ankles behind his ass. Then he began to fuck me in long, penetrating strokes; mashing our pubes together in our dance of love. When I finally felt my orgasm start I jammed my hips up as he stiffened and we blissfully strained together in orgiastic pleasure. As we came down off our high we slowly relaxed and clung together.
"Oh Simone, you're such a great lover. I've been waiting for you all my life."
"Thank you my darling." I whispered back. "I never realized the void in my life until I met you. You've made me a complete person. I enjoy being a woman very much and I also enjoy being your man and a daddy. However, if you want me to suck a cock, I will for you. I love you so much and want to please you."
"Oh Simone. Thank you, my dearest."
We kissed again to seal our bargain. Then I went down on her without being asked and drove her to another orgasm as I recovered my cum from her pussy. Finally, she fucked me with her strap- on until we came again to confirm her dominance of me and then we slept in one another's arms the rest of the night.
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To be continued