From Sam To Sarah: A Genre-bending Story Of Sexual And Personal Discovery. Chapter 2 free porn video
The anticipation was eating me alive. My girlfriend, Aubrey, a strikingly sexy, gorgeous, blonde, polyamorous, bombshell grad-student and I had been living together for about three months. She had taken my virginity and was the dominant one in the relationship. She had been fucking another guy, Scott, every other weekend for about two months, and I had finally asked if I could be there in the room next time he fucked her.
She sat there, pensively deliberating. Her adorable eyebrows were scrunched together, and her chin was in her palm. Finally, after what seemed like a half an hour of thinking, a big beaming smile graced her face. She bit her bottom lip, the same way she does when she gets horny. I’ve seen this face. I’m sure Scott has seen it.
“Hold on. I need to make a phone call. I think I have an idea of how this can work,” she said.
She practically jumped out of her chair, grabbed the cell phone out of her purse, and ran into her bedroom. I heard, “Hey babe!” before the door shut and muffled the sound. As much as I was in love with her and accepting of our relationship choice, it still hurt a little when she called him “babe.”
She was in her room talking to her side-guy for several minutes. All the while, I couldn’t stop my mind from flashing me images of how I thought her and Scott got it on. I imagined her on all fours (a position she rarely let me partake in) with Scott’s muscular body behind her, his cock pushing in and out of her tight, velvet pussy. I imagined his hand pulling back on her straight, blonde hair. I imagine her on her back and Scott shoving his thick cock into her throat, making her gag.
The door swung open and Aubrey returned to the kitchen with an even bigger smile than before. She had gotten what she wanted.
“He’s into it?” I asked.
“Well, sort of,” she replied.
She paused again. She was trying to figure out how to say what she was going to say. Again, my heart raced.
“Well, what?” I asked.
She took a deep breath in and finally told me what she had been planning.
“Look. There’s no way he would be into letting another guy into the room, especially one that I am seeing – which he doesn’t know by the way – while we have sex.”
“I thought you said, ‘sort of’ though. What does that mean?”
“You can be in the room next weekend,” she giggled, “because I told him my lesbian roommate wanted to see what a girl getting fucked by a guy looked like.”
At first, I was confused. What lesbian roommate? Slowly, however, the reality sat in.
“You mean you want me to pretend to be your lesbian roommate, to dress up like a girl to watch you get fucked?”
She could tell I was nervous and apprehensive, so she changed her tone from triumphant to consoling.
“You said you wanted to be there, Sam. This is the only way that I could think of that can make that happen. Scott was totally cool with another girl being in the room to watch. He said it would be ‘so fucking hot to have a gay chick watch him fuck’ me.”
She twisted in her seat a bit. Clearly even talking about this idea was getting her horny. I sat there stunned, trying to wrap my mind around the situation. She reached out and touched my hand, slowly stroking her finger back and forth.
“What do you think about that?” she asked.
“I don’t know what to think,” I said, “there’s no way he would believe I’m a girl. That’s ridiculous!”
Her tone became more serious.
“Look, babe. Honestly, you’re pretty girly as it is. That’s one of the reasons I need Scott every couple of weeks to get that feeling of being taken by a man.”
As she spoke, I knew she was telling the truth. She continued.
“We’re planning on hooking up next weekend. You don’t have very masculine features, and your chubbiness,” she reached out pinched my love handle with a smile on her face, “makes it so you don’t have any predominant masculine feature. I’m sure that if we got you dressed in the right clothes, I did your makeup really well, and I gave you some pointers on how to act more feminine, that you could definitely pull it off. To tell you the truth, I’m really turned on by the idea!”
She came close and started to kiss my neck, her hand reaching into my pants.
“Don’t you want to be my little lesbian roommate?” she said.
Without waiting for my reply, she dropped to her knees and gave me the best blowjob she ever had. After I shot my load into her moist mouth, she swallowed it and stood up.
“We have ten days,” she said, “girly training starts this afternoon.”
The next ten days would be a pivotal era for our relationship. The rendezvous would be on the last day of class before winter break, so the plan was for me to go throw her “Girly Training” sessions for the next ten days, and then, on the day of, she would take me to the salon to get my hair and nails done, and then I could cut it back to normal before classes started back up.
I was exceptionally nervous about the arrangement. Scott was so much bigger and stronger than me that I thought that, if he found out, I could be in some serious physical danger. I was also unsure of the whole crossdressing situation. Sure, I had always had an extreme appreciation for women – to the point that sometimes I couldn’t tell if I was lustful or envious of them – but I had never done anything like this before, and I was a shy, introverted person to begin with!
Girly Training, Day One began that afternoon. Aubrey sat me down in the chair across from her and we worked on hand gestures and sitting posture. I was clumsy and awkward at first.
“Just embrace it,” she said, “I know you have some inner femininity in you. You love me being dominant with you, you like to please me, you like to cook and clean this apartment, you’re a little shy – doesn’t that sound like an undergrad girl to you?”
Her implications dug deep into me, but they worked. I somehow started channeling those feelings in my movements. She told me I was getting much better!
Day two was walking. First with bare feet. I had always noticed the graceful and bouncy way that girls walked, but I never knew exactly how they did it. Aubrey stood behind me, grabbing my hips while I took slow steps and moved my hips for me. After an hour or two, I started to get the hang of the hip-swivel-walk, as she called it. When I had it down-pat, she ran into her room.
“You’re doing so good, babe. Now put these on!” she said with a giggle.
She handed me a pair of 4” shiny, patent-leather pumps that she had apparently purchased for me earlier that day.
“Oh, my god,” I stammered, “you want me to where heals?”
“Of course! Now put them on and we can practice making that little bubble but of yours really bounce!”
To my surprise. It only took another hour of practice before walking in them felt like second nature. Aubrey was impressed and told me as much. Also to my surprise, I was really starting to understand why some girls loved wearing heals. The clicking on the ground, the way I bounced when I walked, and how they elongated my legs was really empowering … in a quite feminine way. I wasn’t even mad when she told me I had to wear them around the house for the rest of training. Was I starting to enjoy this?
Days three through six were almost entirely voice training. This was difficult. I didn’t have a deep voice, but the way girls speak is so much different. It’s airier, more bubbly, and has completely different inflections. Aubrey’s training was spectacular. I could see why her undergrads always gave her high ratings on her reviews for the classes she taught.
Miraculously, by day seven, I could to really throw my voice in a somewhat convincing manner. Aubrey had me call to order take out, and call customer service lines to see if the operators would answer back with “Misses” or “Ma’ams.” They did. I don’t know why, but when they did I was happy.
Day eight was hygiene. Aubrey woke me up with a hand job and then told me to get in the bathroom and rub Nair all over my body and wash off this “nasty boy hair” as she called it. I did like I was told. I walked into the bathroom and covered every inch of my body with the pink slime. I could smell the hair burning.
When I stepped out of the shower, I was smooth all over. She opened the door and saw my now smooth, slightly plump little body.
“Oh. My. God!” she exclaimed, “you have such nice curves!”
My classes had ended by then, so Aubrey saw no problem with grabbing her tweezers and telling me it was time to get my eyebrows shaped. I was so nervous. Up until now, everything I had done could be hidden, but getting my eyebrows shaped meant that the next time I stepped out of this apartment it would have to be in female mode.
Nonetheless, I submitted to her, as I always did. She gave me one of her pink robes. The softness of it was a brand-new experience on my hairless body. It was so sensual and invigorating. I was starting to understand why girls enjoy getting pampered. I sat in the chair while she went to work, painfully yanking each individual hair out of my face and creating a feminine arch.
On day nine, Aubrey woke me up with a blowjob. It was different this time. She wasn’t sucking as much as she was licking, and her hands were more active. She was rubbing me up and down. She pinched my nipples and squeezed what natural boobs I seemed to have from my chubbiness. It was a whole different experience – more sensuous than ever before.
After I came, she gulped down my cum and started talking.
“I have to buy clothes for you today,” she said, “my stuff is a little too small, I think, and we need to get you some girl’s clothes so that your eyebrows don’t stand out when we go the salon tomorrow. The problem is, I don’t know what your lady-style is.”
She looked around the room for inspiration. Her eyes stopped on one of the posters on my wall. It was of the pop-bunk band Paramore.
“I got it!” she exclaimed, “you’re going to be my little lesbian rocker.”
A giant smile crept across her face.
“There’s another thing. Day nine is naming day, babe. We need to give you a girl name. I think its important that you pick it, though,” she said.
I searched my soul for something that was fitting, something that felt right. Almost without trying, I blurted out, “Sarah!”
“Of course!” she giggled, “well, my sexy Sarah, when I come back we get to have a dress rehearsal!”
While she was gone, I took the opportunity to really reflect on how all these changes made me feel. I sat on the couch and rubbed my bare legs together, enjoying the smoothness. I ran my hands up and down my body to experience the new softness of my exterior. I practiced my hand movements and speaking.
She came back with bags and bags of clothing. Bags from H&M, Macy’s, Payless Shoes, Sephora, Michael Kors, and Victoria’s Secret. For some reason my heart pitter-pattered when I looked at the pink striped bag.
“Aren’t you excited, Sarah?”
Being called Sarah already felt so natural. This was taking me by surprise. All this feminine training must have really been paying off.
“Actually, yeah,” I said, “I am excited!”
“Good! But there’s one more thing we have to learn before we can dress you up. We have to learn how to tuck in that little clitty of yours so that you don’t have a bulge in your skirt.”
I was nervous. I guess I hadn’t thought I would be wearing a skirt. I thought it would be something more conservative. She pulled up a YouTube tutorial and we both laughed with nervous little giggles as the demonstrator showed how it was done. After the video finished. Aubrey reached into the Victoria’s Secret bag and pulled out an incredibly sexy pair of lacey black boy-short type panties. These were much sexier than I thought I would be wearing!
I stood up and put my legs through the holes. I slid the panties up to my mid-thigh and then proceeded to push my testicles into my stomach and stretch my cock back like they had said to do, all the while Aubrey looked on wide-eyed. Once my hardware was tucked in, I pulled up the panties to hold everything in place.
“And just like that,” Aubrey said, “Sarah is officially born!”
She ran over and kissed me deeply, passionately in a way she hadn’t before.
She had me try on several outfits before finally picking the one she liked best. I wasn’t yet allowed to look in the mirror. She had bought this special kind of bra that really squeezed what was now my ‘natural cleavage’ together and filled out the rest with these silicone bags. She took out the makeup she had bought and brushed some dark lines on the insides of my breasts.
My breasts? I thought about how odd that was.
She brushed on a highlight to the top of my cleavage. She also applied makeup to my face – eyeshadow, blush, lip-liner and lipstick, and glued on some fake eyelashes.
“Okay, Sarah, go look at yourself in the mirror.”
Aside from my still boyish shaggy haircut, I was stunned at how much of a hot rocker chick I looked like! She had dressed me in a loose-fitting, off-the-shoulder Ramones t-shirt that showed the bra straps hanging on my shoulders. On my hips was slug a slouchy studded belt. I was wearing a sky blue jean skirt with a frayed hem resting two thirds of the way up my thigh, just high enough to give a little peek-a-boo of the lacey apex of my sheer black stockings.
“You look so fucking hot,” she said.
I couldn’t help but agree! Looking at myself in the mirror I saw one of those girls I would be drooling over at concert while her boyfriend stood behind her with his hands on her hips. I was floored and, for some reason, proud. There was something inside me that was truly happy with what I saw in the mirror.
“Everyone at this party is going to be all over you!” Aubrey exclaimed.
My heart sunk. What party? I thought I was just going over to Scott’s house with her.
“What the fuck, Aubrey?” I said, somehow in my girl voice without trying, “I thought this was going to be a private thing.”
She looked a little taken aback, but a little devilish.
“Why would we be going through all this trouble to make you passable for you to just sit in a room and watch me get fucked?” she said, “we could have done that with half as much work! C’mon, babe, I want to show my sexy little lesbian roommate, Sarah, to the world!”
I was exceedingly nervous, but agreed that we had come to far now. And, looking in the mirror, I thought I had a decent shot at pulling this off. Did I actually want to do this?
On day ten, the anticipation was almost unbearable. I was a bit of a nervous wreck as I put back on my sexy rocker girl outfit. After I was dressed, Aubrey took me to a salon where I got my hair, makeup, nails, and toes done. When they spun me around in the chair, I was floored. I now had a sexy little chin-length hair cut with bangs. The bouncy curls on the sides framed my face perfectly to make it appear sexy, soft, and feminine. Maybe this would go well, and nobody would know my secret!
My fingers wouldn’t stop shaking as we drove to the party. Aubrey looked over at me and saw how much of a wreck I was. She pulled the car off the road and into an alley, and told me to step out.
“What? Why?” I asked.
She told me to just do it. Then she followed me out. She pushed me up against the wall, dropped to her knees, pulled my little clitty out of my panties and sucked me off. I couldn’t help but think how this would look if someone happened to walk by – one gorgeous girl sucking the cock of another. What a thought?! She took my load in her mouth and then tucked my cock back in, securing it behind the lacey front of my panties.
“There,” she said, “now hopefully that took some of your nerves away, and hopefully nothing arouses you and makes that little clitty of yours pop out and blow your cover.”
I hadn’t thought of that. But I figured that by the time I was watching her get fucked, I would be alone with them and could probably hide it well enough from Scott.
We got back into the car and resumed our drive. When we pulled up in front of the house, Aubrey turned and looked me deep in the eyes. She took my delicate, manicured hand in hers.
“You look so sexy tonight, Sarah,” she said, “you are going to do great. Just remember the story. You are my sexy little lesbian roommate. The guys here know you’re a lesbian – I think Scott told them as much – so you shouldn’t get hit on too much.”
Hit on? Hit on! I hadn’t thought about that either. What the hell would I do if I guy decided to hit on me?
“You have touch-up makeup in your bag, and you know how to fix it up in case it gets smudged, right?”
“Right,” I said, my confidence building.
“And I put tampons in there just in case another girl asks for one.”
Another girl. That made me feel good for some reason.
“There’s also some mace in there just in case something awful happens,” she said.
There were so many thoughts and worries I had never experienced as a boy. I was carrying mace now? I knew what that was for – in the case some guy forced himself on me. The mere thought was enough to send shivers down my spine.
“Take a deep breath,” Aubrey said, “remember all the training we’ve been doing. Let out your inner girl and your actions will match the fucking hottie that I’m looking at right now. Ok? Are you ready for this?”
I took the deep breath she suggested and replied.
“I’m ready. Let’s do this.”
We got out of the parked car and our two sets of heels clicked on the pavement as we walked arm and arm toward the party.
... to be continued.
Alma
- 17.01.2022
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- Crossdressing
