When I opened my eyes, I was standing in front of my sister’s full length mirror. Believe it or not, I was so surprised at what I saw I had to look up at my face to make sure it was really me standing there. I would say that the sight took my breath away, but that’s such an understatement and doesn’t really describe the way I felt about the way I looked. I think the best way to describe it is this: I was a girl.
The skirt was made of wool, red and white checked, almost like a school girl skirt. I could see that it really didn’t wrap around enough to be my size since the flaps only overlapped an inch or two. It was incredibly short and when I moved, I could see the top band of the stockings peek out from under the skirt. Pulling the flaps apart, I got my first glimpse of my panties pure white, with a huge bulge running up the middle. I saw mom’s reflection in the mirror checking me out to gauge my reaction, and she was trying to hide her smile, but not doing a very good job of it.
With the exception of the bulge in the front of my panties and my hair, I had been transformed into a girl. I never had any interest in stockings before, but as I rubbed my legs together and ran my hands over them, I decided that was going to change. My hands traveled up to my bra, and as I touched it, I turned from side to side, looking at my reflection. I squeezed the cups covering my non-boobs and found the bra was, as she said, very well padded. But, looking at the reflection of my profile, it was obvious that I now had a ‘bust’. Maybe not a big one, but it was the chest of a girl, not the chest of a guy.
Admiring my reflection, I hadn’t seen her slip away from Linda’s room. But, I saw her when she came back through the doorway, smiling and holding something small in her hand.
“Bobby,” she said, “if you really wanted to go all the way dressing up as a girl, we would need to get you some clothes of your own, do something about your hairy legs, your straggly hair and your rough skin. But, you’re just as cute as you could be the way you are… there’s just one last thing I want to do now.” She stepped behind me so I couldn’t see her and after just a second or two, I saw her finger come up and touch my neck right behind my earlobe.
“We have to be careful with this,” she said, “I don’t want your sister, and especially your father, to be able to tell when they get home. This is my favorite perfume, baby. It’s not cologne, or any of that cheap stuff. I only use a tiny, tiny bit on special occasions and I love the way it makes me smell. The problem is that when your father smells it, all the blood in his body goes south and the only thing on his mind will be sex. Isn’t that devilish? Seriously, I’m not kidding, this stuff drives him wild. So, we’re only going to use a smidge and maybe it will help you feel a little more feminine. It’s called Halston.”
It wasn’t long before I could smell it. As soon as it hit my nostrils, I immediately recognized it. Yes, I had smelled it before wafting through the house and yes, it was as good as she said. I felt warm knowing she’d shared one of her special feminine secrets with me.
She stood next to me and we looked at each other in the mirror. “Seems a little foolish to spend all that time getting ready and all dolled up just so I can undress you and do what we’re about to do, doesn’t it?” She asked.
“It doesn’t seem foolish to me, mom.” I answered. “I can’t describe the way I feel right now, but, I feel good. It’s not like dressing up for Halloween or anything like that. I know you’re overdoing all of this strictly for my benefit kind of a ‘try before you buy it’ kind of thing. I really appreciate that, mom. Really, I do. And I’m really ready for the rest, too.”
Turning to me and resting her hand on my chest, we looked into each other’s eyes and kissed very softly, pecking each others lips several times. “That’s true, Bobby.” She said. “I’ve tried to lay it on pretty thick since I don’t know if we’ll ever have a chance like this again. I pushed you emotionally and physically and I swear I’ve never seen a boy or a man get hard as often or as fast as you can.”
We chuckled together for a minute and then she continued, “Seriously, Bobby, I’ve done everything I can to give you little tastes of the things we talked about, and I’ve exaggerated some things, too. I just thought that if you never got another chance to explore and talk about these things, at least you would have had at least one chance…. with me.”
We kissed again, and I told her I loved her. “I know, baby,” she said, “I know you do, and I love you, too.”
We looked into each other’s eyes for what seemed like a long time as we hugged. Before she spoke, she patted my tits, smiling as she fingered the cups of my cotton bra and then she said it. ‘It’ was the words that I knew she would have to eventually say to me before she fucked me and when my father and sister’s return was imminent.
“Baby, in just a few minutes I’m going to take you by the hand and lead you to my bed where I’m going to make love to you the way you asked me to. You’ll have to forgive me for telling you earlier that I was going to ‘fuck’ you, I know that sounded harsh, but I had to see if you really wanted this…. I can see now that you do. I want you to treasure this time so much, Bobby, because you’re only innocent once. When you lose your virginity, everything changes, baby. So, I’m going to make love to you slowly and gently and I’m going to try to make it something special between us that you’ll remember forever. Granted, maybe it’s not the same virginity you want me to take, but, it’s perhaps the best I can do for now.”
“There’s three things I want to say before we do this.” She said. “First, once your father and sister get home, we have to go back to normal. I don’t know what will happen in the future, but when they get home it has to appear the same as it was when they left. Second, I want you to promise me you’ll think about talking with your father. I said this before and I’ll say it one more time. Just give him a chance, that’s all I’m asking. And lastly, remember there’s going to be no regrets, no shame and no guilt.”
“Mom,” I began, “I already decided I would try to talk to dad and I was planning to ask you to be there with me. As long as you’ll do that, I’ll give it a try. It’s not that I don’t trust what you said about him, it’s more that I want you to be there, too. And, I understand about going back to normal, I knew we would have to do that.”
“Good.” She answered. “Are you ready then?”
“Oh, yeah,” I replied, “I’m more than ready.”
“Well, let’s have a quick look at you then and we’ll see if we can get the show on the road. Pull your skirt up for me, sweetie.” She asked.
She stood in front of me with her arms folded across her chest and her breasts cradled upon them. I got a huge burst of excitement as I reached down and lifted the hem of my skirt. “Lift it all the way up for me, sweetheart,” she asked, “I want to check inside your panties.”
I almost came when she said those words. I lifted the skirt above my waist and stood there as she looked at me. I felt deliciously exposed and exhilarated at the same time, too. It felt delightful to stand in front of her like this. I felt my face turn red and my heart rate increased, but I knew that was because of the excitement, not because I was embarrassed. I proudly held my skirt up for her to see me. My cock was angrily pushing against the cotton panties which were tented out by the force of my erection. She stepped forward and put her hands at the elastic of my panties and pulled them out so she could look inside. When she did, my cock perched out toward her, now free to seek its own erect angle. The condom was still firmly in place, but it was obvious there was a significant amount of precum trapped inside. As my cock strained toward the ceiling, she twisted it from side to side to make sure the condom was secure and when she was satisfied, she held my cock against my belly and then pulled the panties back in place and rubbed me for a few seconds.
“I think we’ll just leave the condom on, sweetheart.” She said. “It’s been my experience that guys will either cum spontaneously or eventually masturbate themselves while they are getting it with a strap on. Remember this morning when I put my finger in you?” She asked.
I nodded my head, answering “Oh yes, I remember.”
“Well this will feel a little different than that, I imagine.” She said. “We’re going to use the dildo you’ve been sucking and it’s long enough for the tip to easily massage your prostrate gland. Maybe I shouldn’t say this, but, Uncle Mike and your father both cum bucket-fulls with the strap-on. It can actually be kind of violent sometimes; at least it looks that way to me because it sneaks up on them and the next thing you know they are shaking and convulsing and literally spraying cum everywhere. It might happen to you, too.”
I didn’t know if she was telling me this to warn me or to tease me. To be honest, it sounded wonderful to me and wearing the condom wasn’t a problem to me. I just wondered if she had an ulterior motive with the condom that she wasn’t telling me about.
“Here’s my best advice, Bobby.” She continued. “Most of all, don’t stiffen up on me. I’m not going to hurt you, you’ll see. And, try to relax, especially those muscles you use when you clench your butt together.”
I nodded my head to say that I got all that.
“When you feel it going in, press back with your muscles… I know this sounds gross, baby…. but, like you were going to the bathroom. That will open you up. Once you get used to it, it’ll be fine, and I think you’ll really enjoy it if you relax, let me do the work and just let it happen. Think ‘submissive’ sweetie.”
“Okay,” I said, “I’m not going to fight it, Mom. I want to do this.”
“I know you’re saying that now,” she added, “but when we get in there, something might distract you and make you might lose your focus. Sweetheart, this can be one of the best feelings you’ve ever felt if you just let it happen. I’m not trying to brag, but, I’m pretty darn good at this. Just relax and trust me. Okay?”
I smiled and hugged her. “Really, mom,” I said, “there’s no need to worry. I trust you.”
“Well.” she sighed. “I guess this is it.”
“Yeah,” I answered, “I guess so.”