Baby Girl and Naughty Boy Ch. 07

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"Uh huh," Patty answered as she nodded her head, "Did you ever think about sucking him off, too?"

"To tell you the truth, yes I did." I told Patty directly and honestly. "I had a lot of conflict rolling around in my head that night about it." I replied.

"Ohhhh, Paul," Patty sighed, "what stopped you and why haven't you ever said anything about it?"

I told Patty the night it happened in the store, I was so surprised at the situation, I was initially petrified to do anything except stand there and let him suck me. Looking at Patty, I added, "But, if you would have told me to do it, I would have."

"You're kidding!" Patty exclaimed.

"Not at all." I answered. "That night I would have done anything you told me to do. I feel the same way now -- even more."

"So," Patty asked, "if I set something up with Fred and Wilma and told you I wanted to see you suck Fred's cock, you'd do it?"

"Yes." I said, embarrassingly.

Noting my obvious embarrassed condition, Patty told me there was no reason to feel self-conscious and we talked about it in great detail. I told her I'd always had some curiosity about sex with another guy, but, the opportunity never availed itself, and once I'd met her, I didn't want her to think I was 'Gay'. Patty said that just because I was curious about it didn't mean I was 'Gay' and she told me she didn't have a problem if I wanted to try it sometime. I confided in her that I'd thought about it more and more once I realized it would turn her on, but I was very careful to add that I didn't want anything to come between us.

"I think you should do it," my angel encouraged, "you'll never know how you feel about it until you actually try it. If it's not something you like, you'll know. And if it turns out to be something you want to do again, it could be something we can share.... you know, something we can do together. I love giving blowjobs," Patty continued, "feeling a hard cock in my mouth..... and I totally love the taste and feel of a man's cum, so it's easy to understand how you might want to do it, too."

Her answer was nothing short of implied permission to suck a cock - and unless I missed my guess, she was encouraging me to do it. When I asked her how far she'd want me to go with another guy, she answered, "All the way, if you want to -- as long as I can be there to watch."

It was at this point I took the time to explain to Patty that I had an intense fear of something as big as a man's cock up my ass. I had all these visions of my poor butt being impaled by some joker with a ten inch cock who just wanted to fuck my ass without using any lubrication or taking any time. I didn't want to be simply bent over and fucked. "Oral sex," I told her, "is something I think I could do fairly easily right now; and I wouldn't ever think about doing it unless you were there with me. But," I added, "the thought of anal sex with a guy terrifies the hell out of me."

Patty said she could definitely understand -- not only from a pain and comfort point of view, but also from an emotional point of view. "It's like the most submissive position anyone could ever be in," Patty said, "being bent over and knowing you're in that position for only one thing -- to let someone stick something up your butt. And once they do, you have stay like that while they pound it into you. I'm sure it's worse for males than it is for females, though."

Patty went on, adding "I think all females eventually accept the fact that all our holes are going to be used by a cock -- our vaginas, our mouths..... and out butts, too. But for a guy," she added, "I imagine it could be traumatic and humiliating. I admire you for being open to it, though."

Even having said all that, my A-Cup angel honestly admitted she was extremely turned on by the thought of both oral and anal sex between two guys. She said she wasn't trying to push me into anything, but wanted me to know she wouldn't see it as 'Cheating' as long as we did it together. She was, however, very firm about the fact that we should never consider doing anything with someone we didn't know or didn't trust.

Patty suggested that we get some toys from the local adult store and experiment to see what I liked. She seemed to think getting an assortment of different sized and shaped items might help get me over my fear of having something larger than her finger up my butt, and that seemed logical and appealing to me.

So, a few days later, my A-cup angel and I went to the adult store and bought a bag full of different kinds of anal toys, along with different types of anal lube. Patty's eyes lit up when she saw the strap-on harnesses for sale there, so we bought one along with an assortment of fake dongs to go with them. The love and tenderness Patty displayed during this period of our relationship was very much appreciated by me, and even though I knew she was doing this partly to satisfy her own desires, I knew without a shadow of a doubt her concern for my emotional and personal well-being were always put ahead of her own interests.

The night we first tried the strap-on, I was over at her house visiting. I wasn't expecting anything other than a kiss or two, but knowing Patty, she probably set the whole thing up with me in mind. PJ was conveniently out of town until the next day, so Patty and I had the huge mansion to ourselves. I felt so shameful walking through the big house with just my undies on, praying there weren't any security cameras there. . "Come on," Patty urged, "I do it all the time. I've been all over this house completely naked, you Naughty Boy." And with that, Patty pulled me out of her bedroom with just my bra and panties on. We raided the kitchen and took a basket of snacks and a bottle of wine back upstairs to Patty's room where she kissed me and asked me to put myself in her hands for the evening. "I've got a little surprise for you, but only if you promise to be a good girl for me." She said.

"Good girl?" I thought.

Patty went to her closet and pulled out a big box wrapped with a huge ribbon. "Ta Da!," she said excitedly, "It's for you!"

Patty had the hugest smile on her face I've ever seen, and taking me by the hand, she led me to the bed, sat me down and handed me the box. This was just like Patty, she was the most thoughtful person I'd ever met and it was perfectly in her character to give thoughtful presents and surprises.

I took a long time to open the box, meticulously removing the ribbon as slowly as I could, knowing full well it would frustrate her if I didn't rip it open to see what was inside. When I finally opened the box and peeled back the yellow tissue paper, what I saw made my heart jump -- and my cock jump, too.

I'm not sure how Patty pulled this off, but she'd found a seamstress somewhere on the East Coast who made their living making intimate feminine apparel for men. In this case, Patty hired her to make me five different nightgowns, all based on the 'Baby Doll' style I told her about from my childhood memories. Not only that, each one came with a matching pair of rumba panties, which Patty immediately pointed out had extra material in the front so a man's erect cock would have plenty of room.

They were all different colors, but two of them caught my eye. The first one was white and it was made of pure silk. It had thin shoulder straps and the length came down just below my waist. There was a single row of ruffles around the very bottom and it was light as a feather. The other one that immediately got my attention was light purple in color and made of nylon. The cut of it and the way it looked reminded me exactly of my sister's baby doll nightie I used to wear -- the same one my mother caught me in that day I was admiring myself in Sissy's mirror.

But, they were all beautiful. Patty showed me the inside of each one, pointing out that nothing scratchy would ever touch my skin. Each baby doll was slightly different than the others and I could tell that Patty probably went to an incredible amount of effort to have these made for me. "We'll keep two here," Patty said, "and you can take the other three home with you. But," Patty continued, giggling, "that's just the first half of the surprise."

With her eyes twinkling, Patty announced we were going to play "Mother and Daughter Dress Up" and we were going to play with the strap-on toys. She immediately worked to put my mind at ease, saying we would go slow, use a lot of lubrication and she would let me pick out which dong I wanted her to use with the strap-on. Patty said she'd thought it all out, taken my fears into consideration and she was sure we could do it in a way that would give me a wonderful first-time experience.

"Will you let me do this for you?" Patty finally asked after she explained everything she had in mind.

Patty had a way of making things happen. She would meticulously plan and set things up to the point where all I ever had to do was be there. She never spared any expense or effort and never gave away what she was planning to do until it was time. She never put me in a position where I felt vulnerable or adversely surprised -- I think that's because she never did anything until she looked at it from all angles. This was one of those times where she planned perfectly and presented it in such a way that I had no option other than to love her for it and agree to everything.

Patty jumped for joy and ran to her closet and brought me a bag full of things she said we would need. It was filled with all kinds of girl things -- shampoo, conditioner, nail clippers, nail files, special washcloths, conditioning creams, and delapidory creams. "We're going to turn you into your sister again," Patty said, "just like your Mom did... but only for today. I'm going to show you everything girls do to make them selves soft and 'girly' and we'll see how you like it. Then later, I'll make love to you with the strap-on and you can stay here until Daddy comes home tomorrow."

I took a few minutes to visualize what Patty said. I'd previously told her the entire story of how my Mom dressed me in my sister, Sissy's, clothes that time before I went off to college and let me be her 'Daughter' for a couple of days. I'd told her all the details of how much I enjoyed it and how my mother made it such a memorable time for me -- one of the best few days of my life. Mom pulled out all the stops, too; even giving me a long and detailed gynecology lesson using herself as the subject. She talked to me just like I was a girl and we had long discussions about emotions, feelings, and every sexual topic under the sun. Mom was the first one to ever discuss anal sex with me and explain about the pleasure and stigma surrounding it. She was specific when she talked about cleanliness and the emotional connection between someone's butt and their sexual desires and fears. I could see in Mom's eyes that she was speaking from experience on much of it, and one thing I took away from that specific discussion was that it only took one bad anal experience to make someone shy away from it forever. She gave me a piece of advice I've never forgotten, and that is: "Don't ever expect your partner to do anything you wouldn't do and always treat them better than you would want them to treat you."

So, Patty was offering me a way to safely be a girl and we would go all the way with it -- all the way with the mother tenderly fucking her daughter's ass. She was going to show me how to prepare myself and how to use all the things she bought me. Patty was going to remove all my body hair, too. In effect, I was going to be a girl in almost every way, shape and form. She was going to 'Make Love' to me and I would sleep next to her; safe and sound next to my 'Mother' when it was all over.

Damn, I loved that girl. One thing bothered me, though, and I brought it up.

"You know," I said to Patty, quite embarrassed, "I don't have any desire to be a girl..... you know.... full time. You realize that, right?"

"I know, Baby." Patty answered. "I get the fact that it's a fantasy and a role play for you. I'm not trying to turn you into a fem or anything like that, but I don't see any reason why we can't incorporate this into our relationship if it's something we're both interested in."

"Baby," she added, "it turns me on just as much as it turns you on, and it can be something just for the two of us to share. Plus, you might even discover some things about yourself that have been there a long time, and you never realized it."

"And what would that be?" I asked.

"Well, for starters, maybe you'd like to have a male lover from time to time." She answered, taking my hand in hers.

"Ah," I said, laughing, "you'd like that wouldn't you? That's one of your fantasies."

"Okay," Patty answered, "that's true, I would like to see that.... but, I think you're interested in it as much as I am, you're just afraid to admit it, Naughty Boy. You're afraid it will make you look 'Gay' or less of a man in my eyes. I assure you, though, that's just not true at all."

I understood what Patty was saying, and she was right for the most part. I'd always had some degree of bi-curiosity and repressed it because I was afraid of what would happen if people found out. Having Patty as a willing partner to all of it was a blessing, or at least it was looking that way.

For the next several hours, Patty took me under her wing and started my transformation into my sister. We spent the better part of three hours in her huge bathroom. When I emerged, I'd had a shower, a soaking bath, my body hair was removed, all my nails were cut, and my skin had a soft, supple feel that was amazing. I never realized how many things girls do to them selves to make them cute and pretty, but she explained everything as she went and showed me how to do it myself, saying I could do these things on my own at home if I wanted to, and offered to help me in any way she could. "No one will ever know but me, Paul, and I'd love to help you with this." She said.

Throughout most of it, I maintained a healthy erection. Patty tried her best to ignore it, but after a while, she gave up, saying "I guess it just means you like what we're doing." And I did. The whole process was incredibly erotic and it gave Patty and me a different kind of 'together' time. It was a time where she was the hands down expert; she knew exactly how to do it and she not only made it fun, she made it successful. But, be sure of this -- Patty didn't want me to cum while we were 'Getting Ready'. She didn't touch me much there, except while she was doing the hair removal, and she kept an eye on me to make sure I didn't try to touch myself, either.

The whole time, Patty was dressed in just a pair of panties and a girl's cotton vest top with little flowers on it. I imagine the vest top was intended for a child, but it fit her small frame and tiny boobs magnificently. It was probably sexier than her being naked because the panties crept up between her pussy lips and she left it like that the whole time, knowing it would hold my attention and keep me agitated.

When the time came for me to put on the Baby Doll and the rumba panties, I was just as excited as Patty was, maybe even more, and my erection proved it. Patty started to role play as my mother and referred to me as her little girl or her daughter numerous times. I knew she was just playing our little make believe game, but she took great care in doing it lovingly, speaking softly and touching me innocently. It was nice -- very nice, and even though I knew we were pretending, the way she handled it made it seem warm and inviting. When Patty picked up the rumba panties from the bed, she looked at me and took a deep breath and let out a sigh.

"Let's get you dressed now, little girl." My A-Cup Angel said quite calmly.

Those words rang in my ears as she motioned for me to come closer. When I did, she put her arms around me and we hugged for a few minutes. "Whatever happens with all of this," Patty whispered, "whether you like it, or not, and regardless if we ever do this again, I want you to know that I love you now and I'll love you afterwards, too. None of any of this changes the fact that you're the man I love with all my heart."

With that, Patty bent down and held the panties out for me to step into; first one foot and then the other. Once I stepped into them, Patty pulled the panties up my legs and settled them on my hips. The panties felt light and airy -- and my hard cock poked out, billowing the gathered material of the rumba panties out in front of me. They weren't tight at all. The leg and waistband was just right and when I swung my hips back and forth, my erect cock swayed easily inside the confines of the panties. Obviously, the seamstress who made the panties for Patty knew how to accommodate a hard cock. They were tight enough to stay on me, and allowed plenty of comfort room for my full blown erection.

Patty stood back and looked at me. I could tell by the smile on her face that the panties met with her approval. "They're like little girl panties," she observed, "and with your legs nice and smooth now, you really look like a girl from there down..... well, except for this." Patty said, as she reached out to feel my rod poking out in front of me. Unfortunately, when she touched me, my cock lurched and a few drops of precum leaked out onto the panties, leaving a dark wet spot where the tip of my cock touched the material.

"I'm sure these will have to be washed by the time we're done.... at least I hope so." Patty laughed, adding, "I'll wash 'em for you tomorrow after you leave."

As Patty reached for the matching Baby Doll, my heart started to beat violently in my chest. "Come here, so Mommy can put your nightie on." Patty cooed as she gathered up the material so she could slip it over my head.

I took a timid step toward her and when I got close, she said, "Arms up." I raised my arms and Patty reached up to put the Baby Doll over my head and as I slipped my arms into arm holes, I instantly got a rush reminiscent of the days when I used to put my sister's nighties on years ago. I felt a blush starting across my chest, but it wasn't a blush of embarrassment, it was a blush of joy -- a sense of remembrance. It had been so long since I'd allowed myself this pleasure and it felt good -- really good. Patty's eyes sparkled when she let go of the fabric and the Baby Doll fell down, flowing over my body. "Oh, Sissy," Patty moaned, calling me by my sister's name, "its beautiful... you're beautiful. Come look in the mirror."

Patty took my hand and pulled me to her dressing mirror. "Look." Patty said. In the mirror, I saw something that had been hidden for years, but yet something I knew was lying dormant within me. It conjured up such a deep set of feelings in me -- for instance, the way my mother allowed my panty wearing and panty sniffing, the way Mom let me pretend to be her daughter for those few short days..... and I began to realize something. I realized that this is a part of who I am, and then I realized Patty was right -- this was something special.... something intimate and meaningful and it was just for us..... something special and private.

Patty left me standing at the mirror and I couldn't help from twirling right to left looking at myself in the mirror. Even though I had a full erection, with the way the Baby Doll hung on me and the fullness of the hem, I could barely tell I had a hard-on. I embarrassed myself thinking I could even wear this in front of someone and feel safe that no one would tell I was a man. If it wasn't for my short hair and my lack of breasts, I could almost "Pass".

When I turned to find Patty, I saw her pulling the comforter down on her bed. As she pulled it down and then all the way off, it left the rose color sheets visible along with four very large and fluffy pillows.