Can I Try? Pt. 03

The next morning I woke up to the most glorious feeling ever. My best friend Randy was spooning me from behind, his muscular chest pressed against my back, his strong hand on my slender hip, and his morning erection was pressed against my ass. We were both shirtless and so warm and cuddly I didn't ever want to move. The down side was, I really had to pee.

I reluctantly extricated myself from Randy's embrace and went to the bathroom, last night's developments on my mind.

I was no longer a virgin. I had broken through Randy's religious upbringing enough that he had let me give him a blow job and had eventually fucked me in the ass last night. All was right with the world or so it seemed. There was one lingering issue, that of my Mom watching us do it. I knew she had been turned on by it, I watched her masturbate herself to orgasm at the top of the stairs while Randy took me.

What I didn't know was how to handle that little detail. Since he was still asleep, I could feel his hot breath on the back of my neck right now, I didn't know how Randy would handle things in the cold light of day so to speak. These details aside, I could not have been happier.

Things were not at all normal though. It was like ten AM on Sunday morning. Randy would have to leave to go to church with his family by eleven. This wasn't usually an issue when he spent the night because my Mom who is usually an early riser would have us up and eating breakfast by nine. Instead there was not a peep from my Mom at all. The door to her room, which I could see if I looked from the right angle, was still tightly shut. Something was up. Probably just embarrassed, she knew I saw her.

Returning to the couch bed in the living room I looked down at Randy sleeping peacefully. He was gorgeous. I did have to get him up though because his parents would be pissed if he wasn't ready for church. I was bummed he had to go to that hateful place, but if he missed it his parents might not let him come over anymore, that was a fate I just couldn't contemplate.

I could at least send him off relaxed. I looked again to the stairs and my Mom's door was still tightly shut. I gently pulled Randy's PJ bottoms down exposing his beautiful erection. I just looked for a minute with my mouth watering. His cock was just so beautiful, long and straight and throbbing with need, a need I intended to fulfill.

Tucking my long dark hair back I took it up with my long delicate fingers and lowered my soft lips to it. Randy moaned in his sleep as I let my tongue circle the head, which was wrapped between my thick soft lips. I was really gentle as I didn't want to wake him just yet and his moans seemed to be getting closer to consciousness.

I went deeper, letting his thick throbbing cock fill my wet mouth. I pushed down to take it all as my tongue explored his girth and saliva was dripping past my lips. My hand cupped his soft balls as I felt his cock pushing into my throat. I struggled not to gag as my throat contracted then relaxed. I just sat there slowly swirling my tongue around his cock. He was moaning loudly now, probably awake but not saying anything. Then I felt his hand on the back of my head urging me to take him even deeper. My throat was relaxed now so I obliged by sliding my lips all the way down to his base.

Then he was thrusting into my mouth and moaning loudly. It didn't take long for his cock to start pulsing in my mouth. I backed off a little, letting the spurts of cum fill my mouth. I swallowed it all with a sense of the purely sublime washing over me. I was at peace with the world.

"What the fuck dude!"

"What?" I asked sitting up and licking my lips.

"Shit!" he replied ignoring the question but looking at me strange, "I have to get going."

He practically jumped out of bed and dressed in a rush. He was out the door without a word, though he did take one long look back at me, still sitting dumbfounded on the bed with the after taste of his cum in my mouth as he left.

I was upset but there really wasn't much I could do or say about it. My tummy grumbled. There was something I could do about that. I made some coffee and breakfast. Facing my fears I went upstairs and knocked gently on my Mom's door.

"Yes" she replied, her voice cracking weirdly.

"I made us some breakfast"

"Oh that's nice honey... I'm sorry... I'll be down in a minute."

My Mom is usually so upbeat, I really felt horrible hearing her voice. She sounded so down. When she did finally come down my worst fears were confirmed. She looked horrible, wrapped in a big terry cloth robe, her eyes were red and she was sniffling. She had definitely been crying.

She sat down and ate methodically. I poured her some coffee and OJ and sat down to eat with her. The silence stretched on to the point of discomfort.

"Is breakfast OK?" I asked, just to break this stalemate

"Oh Honey, yes breakfast is perfect," then "we should talk."

"OK" I replied as neutral as possible, not really know what was coming next.

"I owe you an apology." She said.

"For what Mom?"

"I intruded on your privacy and I feel like a broke a trust between us."

"You mean last night?" I asked even though it was obvious.

"Yes, last night...I...I"

"Mom, it's OK." I soothed reaching out to touch her hand.

"No Baby, it is not really OK"

"Why Mom," I demanded, "what's not OK, that I'm gay?"

"Ohhh Sweetie no, no, no." she replied, her tone completely changed, "Please don't ever think that. I love you no matter who you are."

"Then what?"

"I watched." She said, slumping in her chair.

"So!" I replied

"I... I... god this is so hard to explain." She started crying really hard now.

"You watched us and liked what you saw," I put it plainly for her since she was having such a hard time, "then you masturbated."

"Yes!" she admitted sobbing, "can you ever forgive me?"

I sat thinking a while. I wasn't upset that she had watched, in fact it was actually was a big turn on. My Mom is a really sexy woman with long dark hair like mine, big hazel eyes and gorgeous curves with big breasts and wide hips. I definitely had a latent attraction to her. Randy practically drooled over my Mom when he came over too. How to address that without her thinking I was a total pervert though. Then it hit me.

"Mom, do you remember a couple of weeks ago when you had Paul over?" I said, eyes downcast.

Paul was my Mom's sometime friend, sometime fuck buddy. My Mom didn't often date seriously, but she did have needs. Again, in our household this sort of thing wasn't really a secret.

"Yes," she replied through her sniffles, "what does that have to do with this?"

"Well, I kind of did the same thing."

"What do you mean?"

"When you thought I went to bed I heard you and well I went to the top of the stairs..."

"You watched us? Me... having sex?"

"Yes."

"And you..."

"Yes, Mom, I masturbated watching you have sex, just like you did last night watching me."

"Oh Honey...Really?" in a quizzical and oddly disapproving tone of voice.

"Yes Mom, I liked it."

"I'm your Mom, you should like that."

"Well I did." I said with finality, raising my eyebrow at her obvious hypocrisy.

"I thought you said you were gay?"

"I don't know what I am Mom, watching you, I wanted to be you... and I also wanted to be him... it was all so confusing and just so... I don't know what to call it."

"Erotic" she finished for me.

"Yes exactly."

It was good to get everything out on the table. We talked a little while longer. She asked me about my feelings for Randy and I told her about his internal conflicts. Soon we were talking the way we used to and all of this confusing stuff was put behind us.

The rest of the day was blissfully normal. I was both elated with what had happened with Randy and glad my Mom and I were on some kind of normal ground again, though there was a lingering sense that we needed to talk some more. I was also sad and nervous that Randy hadn't called or come back that afternoon. One part of me understood while the other part, well I wanted him to be all in and it just didn't seem like it was going to happen.

So on top of it all I had a lingering sadness. I wished he could just be free to be with me however we wanted but all that conservative church crap was in the way. Not for the first time I wished I had just been born a girl and none of this would be an issue, then again, Randy and I probably wouldn't be as close as we were that way.

At dinner that night my Mom brought up the conversation that was lingering between us. Things started of fairly normal. She cooked pork chops while I did the mashed potatoes and salad. We worked happily and hugged several times affectionately. I set the table and we ate for a while in comfortable silence.

"Honey, can I ask you some personal questions?"

"Of course you can Mom." I replied feeling all of a sudden nervous.

"You said earlier that you don't know if you're gay," she began, "did you like what you did with Randy last night?"

OK, so I was glad we could talk now, but still this was not going to be easy.

"Yes" I managed to choke out as I felt my face flushing a deep red.

"I know you sometimes like to wear pretty things," She continued ignoring my embarrassment, "do you ever wish you were born a girl?"

"Ummm, yeah sometimes, I mean I guess so." If possible I flushed even more.

Mom knew I wore girls clothes sometimes. She had caught me a couple of times in her things, at which point she bought be some underwear, stockings and a few skirts and blouses. She had left them in my room without a word. We never actually discussed it.

"Do you think you might be," she replied hesitantly "Oh I don't know what they call it, like transsexual?"

"I don't know, maybe?" I responded through my embarrassment.

"Would you like me to help you find out?" she asked, the earnestness in her expression was heartbreaking. I loved my Mom so much.

"Umm, like how?"

"Well I could go shopping and maybe I could help you with a real look, not just some silly clothes." she replied, "we could do like a makeover kind of thing."

My heart was pounding. This was like the chance of a life time and I really wanted this to happen so badly. Yet in the stupid way of people I was really afraid to admit it. I could feel my palms sweating and my heart thumping in my chest as I built up as much courage as I could muster.

"I guess we could try."

"OK," she replied with a huge smile, "OK, just leave it to me then, this is going to be so much fun."

She gave me a huge hug, her large breasts pressing against my arm. Her enthusiasm was contagious and I found myself excited and more than a little horny at the prospect of her plan. We didn't talk much more about it that night, but I went to bed very happy and my problems with Randy largely forgotten.

The next morning when I got up for school my Mom had already left for work. When I jumped in the shower I noticed that my normal Men's razor had been replaced by a pink one and some women's shave gel. I am not a hairy person and I have always shaved what hair I had on my legs, arms and pubic area. I never really needed to shave my face, just plucked the few hairs I had. It did feel much nicer to use these feminine things on my body and my skin was much softer afterwards.

When I dressed for school I was feeling so great that I even put on a pair of my panties rather than my boy's underwear. No one would know and I would feel really sexy all day.

When I got home that night my Mom was waiting with a ton of bags from stores in the mall. I noticed one was Victoria's Secret and on was Sephora a makeup store as well as several others from woman's clothes outlets. Damn, my Mom had gone all out.

"So I took the rest of the week off of work," she began, "what does your school schedule look like?"

It was mid semester and my grades were good. I only had school on Monday, Wednesday, Friday and I already had my assignments, it wouldn't kill me to miss a few days.

"Great!" my Mom said, "Let's get started!"

My Mom got up and pulled the shades on the windows to block off any view from the street.

"OK strip" she demanded in a motherly tone, "let's see what we have to work with."

I hesitated at first and she just arched her eyebrow at me. I stripped down to my panties. She looked at those with a slight smirk, but didn't comment or laugh. I stood nearly naked in the middle of the living room with my attractive mother scrutinizing my body. She made little comments as she walked around me.

"Hmm, well your hair of course is lovely; we can get away with just a bit of styling there."

She held my hand up and inspected my nails. I took pretty good care of myself and yet still she tsked, tsked the state of my fingers.

She also ran her hand over my hip and across my ass, which to my embarrassment caused me to get hard. My cock is not big, maybe five inches hard, but still out of place. I shifted so at least my cock was flat against my belly rather than poking out a tent in my panties.

"You have a really nice shape." She declared, patting my ass appreciatively, "We can definitely get away with a lot there, very nice skin too Sweetie."

"We'll have to figure out what to do about this though." She said gently running her fingers over my hard little cock and sending shivers through my body. After that she moved on and ignored it.

She continued her inspection of my body, her fingers touching me here and there. She teased my nipples a little and they responded by hardening, I have pretty big nipples for a boy even though I don't have much of a chest.

She stepped back and looked me over one more time. "OK" she said in a business like tone, "we can make this work."

After that she had me put on nice black silk robe and join her at the kitchen table. We were going to start with my nails so she could tell me what else she had in mind. She brought out a bag with fake nails, several colors of nail polish and a bunch of different implements.

She took my hands and talked me through the steps of a proper manicure. She also said we could do each other's toenails later. She shaped what nails I had and removed my cuticles, all the while talking away. It was really starting to feel like we were a couple of girlfriends. She applied fake nails to each finger, holding my soft hands in hers the whole time. The intimacy was giving me the most pleasant shivers down my spine.

"So, what shall we call you?" my Mom asked.

"I've always liked Sophia" I replied, it was weird saying that name out loud.

"Hmm, Sophia," she pondered looking at me and trying it out, "Sophie, Sophia, I like it."

"What color do you prefer Sophia?"

"I like that one Mom." I replied pointing to a nice dark burgundy color with sparkles.

"Good choice, though I think we'll need to work on your voice too, we should start practicing."

"I like that one" I said in my best girlish voice.

"Better, but keep practicing."

"OK" I replied in a high tone.

By the time my nails were done I had settled into a husky female voice that my Mom said was very sultry and believable.

Next we moved to the bathroom so she could do my hair. My dark chestnut hair was already shoulder length so she had a lot to work with. She started out by trimming the bangs in a deep V shape on my forehead. I didn't question it at all until it was done. In my mind I realized that it was kind of a one way street, if I wanted to go back to credibly being a boy I would have to cut it all off, something I definitely did not want to do.

Then my Mom started curling the long strands of my hair to give them a nice wavy appearance. She hummed as she worked.

Then out of nowhere she said, "You know Sophie, I think I like having a daughter."

And there it was. What had started out as an experiment was quickly becoming a transformation to a new reality. There was something in our relationship that just made this feel very right for both of us. There had always been an aspect of the feminine in how my Mom and I interacted, it was always very intimate and sharing and yet just shy of right. This experiment was bringing us closer together and closing that gap.

As for my feelings, a sense of calm and rightness was settling over me. I had never been comfortable with my body really. I was skinny and had effeminate mannerisms. Rather than aspiring to be more macho, I always found myself wishing that people would appreciate my delicate features, that they would look at me and perceive beauty. As my Mom worked her magic that was becoming a reality. Our house had become a fantasy bubble for both of us and I wondered how long it would last.

My Mom showed me how to do the things she was doing, guiding my hands with the curling iron, hair spray and barrettes. She took a couple of strands from my temples and twisted them back and clipped them at the back of my head. She left a couple of curly strands to frame my face. It was an easy to do but elegant hairstyle.

"There," she said admiring her work, "OK now into my room and sit in front of the vanity."

I sat looking in the mirror. The hairstyle went a long way to making me look more feminine than I did normally. I probably could throw on some simple clothes and pass on the street as long as no one looked too close.

"We'll need to get you one of your own," My Mom declared as I sat down, "you'll need a place to do your makeup."

"Wow Mom," I said breathless with anticipation, "you're really getting into this."

"Aren't you Sweetie?" she asked, "am I taking this too far?"

"Oh no, not at all Mom, it's just not what I expected."

"Well I didn't expect to all of a sudden have a daughter either, but life can be exciting like that sometimes."

While we talked my mom applied foundation to my face. She used different colors to create contouring that wasn't really there. She used darker colors in the hollows of my cheeks and under my chin and on my forehead. I was really surprised at how much like painting or other art it is, dark colors move areas back and light areas appear moved forward.

"We'll blend these in so you won't even notice." she intoned as she worked, "They will give your face a more feminine shape with high cheekbones."

She blended the foundation down my neck into my upper chest, highlighting my collar bones and even working the contouring technique into some appearance of cleavage.

"There," she said as she blew on my chest and sat back to admire her work, "that should help until you get boobs of your own."

Boobs of my own... wow. My Mom was all in. It was starting to seem like decisions had already been made, but I hadn't been included on the conversation. While I was thinking about this my Mom started plucking my eyebrows, another semi-permanent change to my look.

"Um.. Mom?"

"Yes, Sweetie?" then, "hold still, I know it hurts, but beauty doesn't come cheap."

"No it's not that," I started hesitantly, I didn't want to spoil her enthusiasm but I did want to slow it down a bit, "do you really think that I should be a girl?"

"Oh Honey I know it seems like maybe I am pushing, but I really find this whole thing exciting. Are you having second thoughts?"

"I know Mom, I really do too. No, not second thoughts really, I am just not sure."

"It's a big change Baby, I was thinking maybe we could approach this week like we are all in and then talk about how to go forward next week. No matter what you decide it is your decision and I just want you to know I love you not matter what."

"Thanks Mom, that sounds perfect." I replied hugging her. I noticed I was still using my girl voice and it was becoming comfortable, like part of who I am.

From the foundation and eyebrows we moved on to my eyes. This part was really artsy and fun. We went with a smoky eye look, with thin dark eye liner. I have really long lashes naturally so by the time we got to the mascara, I was looking really feminine. Each step was bringing me closer to an ideal I never thought possible. We finished the look with lipstick that was a close match for the red on my nails.