To New Beginnings Ch. 05

The next month went by really quickly. It started with the day after meeting the doctor, learning what Jennifer had done and coming to the realization that I not only was accepting of everything happening but also was enjoying it all.

I awoke even before the alarm, made us coffees, did my workout, got undressed in the change room and showered, my head held high, no embarrassment, I got dressed in front of the couple of guys, did my makeup, and headed out. Although, what was weirdest to me about everything was how I was starting to notice guys more, how they looked, if we passed close enough by, how they smelled and I had started to check them out, my eyes always drifting down to their crotch especially at the gym while they were mostly in shorts. I was especially careful of not staring too long... and they were noticing me too. I noticed more and more guys checking me out. I wasn't sure if the looks were increasing from the past months or I was nothing it more.

After leaving the gym, I went out on my own for the first time, first to Sephora to buy all of my own makeup instead of using Jenn's, I spent a bit too much there especially on the perfume but I had the cash from my car, the income from the website, what I was getting from pleasuring Mr. Big and everything I got was needed, or so I reasoned with myself. The girls at Sephora ended up being so helpful, they didn't think I was a guy for one moment, or at least they didn't show it, I had just told them that I grew up in a very conservative home and wasn't allowed to wear makeup... not too far from the truth. The biggest help was getting foundation that matched my skin tone and giving me a few tips on application that Jenn didn't know or hadn't thought to mention. I thought that I looked even better in my own makeup.

After that I went on to several thrift shops buying a week's worth of new to me outfits, the sluttiest things I could find as I was instructed to look for, so that I wasn't wearing the same thing every day or Jen's old gym clothes. Not that I minded wearing her gym clothes, they fit pretty well despite being one size too small. I managed to find a really cute feminine small desk that I could finally set my monitor, keyboard and mouse on. After the shopping was done, I had two appointments that Jenn had set up for me. One to get my nails done, looking down at them, now about an inch long in length, painted bright pink. The next appointment was to get fake eyelashes and lip injections. The injection to the lip wasn't bad but getting fake eyelashes put on strand by strand was a long process. Looking into the mirror after it was all done, it was confirmed, yup I looked like a slut. If I had longer hair and bigger boobs, some would likely call me a bimbo... big boobs would look so hot I thought to myself.

I brought home my haul, thankfully there was guy in the parkaid willing to help bring the desk up to my apartment, so I wouldn't risk breaking a nail. I got it all set up, then knowing myself, cleaned the apartment first before gaming, setting an alarm in case I lost track of time to make sure dinner would be ready for Jenn. It felt good to game again, that was a piece of me that would never change. The alarm did end up being needed, so after it rang from my phone, I made another amazing dinner for us, this time veggie burgers, with a recipe I had found online, with a side salad. She was impressed again by the meal. After dinner she pulled out a small pink leather choker with 'SLUT' spelled out with rhinestones, I put it on and then she fucked me passionately with her strap-on. The choker would hardly ever leave my neck except to shower and workout.

This became my routine for the next month except for the shopping which I still did usually once a week to see if the thrift stores had gotten anything new in, also finding that consignment shops were another great way to get clothes at a better price that were in like new condition. I also ended up adding in doing hot yoga to increase my flexibility, interspersed with taking more pictures and videos of myself and usually with Jenn in them as well, and pleasuring Brent. I finally had his name, I got it the next time I sucked his cock. There was something hot about not even caring about his name and just pleasuring his big cock but I wanted to at least be able to attach a name to a cock. I still added his name in my phone as Mr. Big as we exchanged numbers, so he could see me other times other than at the gym.

That same night Jenn had decided that it was time to downsize my cage. It was the first time my cock had been out of the cage in nearly a month. I noticed my cock didn't seem to get as big after being caged or at least didn't get as big. She let me fuck her. It felt wonderful but for some reason all I could think about was how much I would rather be getting fucked by the dildo. I still came but it didn't feel like the first time. Getting p-spot orgasms so often had ruined any penis stimulated ones. Even the times she had let me use her Hitachi on my dick through the cage while getting fucked felt way better. So, when she locked my cock away in its new one-inch pink cage, I was strangely fine with it. Looking down at my cock in the cage, I wondered if could I even call it that anymore, it was basically a big clit now.

After a week had passed I could truly feel myself slipping into the role of housewife for Jenn and slut. The clothes, getting better each passing day with applying makeup and enjoying all the lacy, silk, tight fabrics. I was becoming exactly what Jenn had hoped... maybe becoming more of a slut then she expected in the beginning.

At the beginning of the next month, I had my follow up with Dr. Wagner. My body had taken well to the new dose, my testosterone and estrogen levels were now in line with a healthy teenage girl which now I felt completely like. I also had managed to lose another 8 pounds down to 137. Dr. Wagner was a little concerned at the rate I was still losing weight and suggested I start upping my calorie intake or start scaling back my workouts. I told him that once I hit my goal weight of 120 that I would. I wanted a little bit of a buffer to put some weight back on to my ass, boobs and hips, now that I had normal female levels of estrogen, that should be doable, especially with the additional months it was going to take to lose the weight. I left with a refill on my scripts and an appointment for follow up in 3 months.

The next day after coming home from the gym, as I was doing a bit of cleaning of the apartment dressed in a pair of tight denim shorts, white tank top and thong with no bra, with the choker of course, there was a knock at the door. I had expected it to be Mr. Big, I called out to the door to give me a second and quickly set up and turned on the video camera, figuring that I might as well get some content out of it.

I opened the door to find Tom, the guy I had met and had lunch with a month ago. I hadn't ended up texting him since then. How did he know where I lived? Jenn... Jenn must have gotten his number from the business card he gave me. He looked really good, giving him a look with new eyes, he was in his early 20s, clean shaven face, stood over me by a fairly significant amount so he had to be at least over 6', in great shape, looked like he played some sort of sport, probably hockey as a lot of boys here did, he had piercing blue eyes and blonde hair.

"Can I come in?" he asked politely.

"Sure." I stepped aside of the door way, giving him room to walk in, closing the door behind him.

He came in and looked me right in the eyes, still full with the same passion for me I had seen a month ago. "Stephanie... Jenn told me all about you... in fact she told me everything over text the same day that we had lunch together... I wasn't sure how to take it all... and then she offered you to me... ummm... sexually... but I'm not that kind of guy, if there was to be a thing between us, I would want it to be out of your liking for me, not because I'm paying... I've thought about it for a long time and I really like you. I don't care that you were born a guy."

I smiled, leaning forward, my eyes closed not quite putting my lips to his but leaving enough room for him to back off or to close the gap and kiss me. He chose the latter. Wrapping his arms around me, kissing me passionately with tongue. It was similar to the way Jenn kissed me but much different. Feeling his strong arms around my body. I felt extremely feminine in the moment. We continued kissing, standing in the middle of the floor until I guided us over to the bed. We practically fell into it, Tom not letting me go out of his arms. When the kiss finally broke, I began to suck and kiss at his neck, reaching my hand under his shirt to feel his hard flat stomach. I pulled his shirt over his head and while doing that, I had noticed he was trying to do the same to mine, I lifted my arms above my head to allow him to take it off. We returned to making out, our naked chests felt amazing up against each other, his hands made his way to my budding breasts, massaging them and then giving my nipple a bit of a pinch. I moaned out in pleasure "harder" which he obliged.

Breaking away from the kiss, I began kissing my way down his chest, stopping at his waist line, looking for confirmation that I was good to continue, he nodded, so I undid his jeans, stripping them to the ground leaving me on my knees in front of him. I began massaging his already hardening cock through his boxers which caused it to grow to its full length. I pulled them off as his uncut cock sprang to life upon being freed. It was nice, reminded me a lot of the dildo Jenn had used on me so many times by this point. Just over 7" in length and decently thick, not near as long or thick as the beast that I had spent the last month sucking on frequently, but still a very nice cock. Tom's cock was wet with pre-cum and throbbing, I took the head of his cock in my mouth, sucking it, twirling it with my tongue, licking it up and down, coating it with a healthy amount of saliva. I easily deep throated his entire cock, bobbing up and down on it. Groans and moans coming loudly from him.

I could feel him tense up but he put his hands on my shoulders, stopping me, I looked up at him, unsure of what was going on. He looked down at me, "Stephanie, I would love to fuck you. If you finish me down there I'm not going to be good to go again for at least half an hour." He laughed a bit at the end of sentence.

I smiled, nodding up to him and crawling back into bed, kissing his lips, he broke the kiss this time, kissing down to my neck, stopping to suck on my nipples which caused me to moan loudly, they were so sensitive now. After he spent a few minutes on each nipple, he continued kissing his way down my stomach, stopping where I had on him to undo my shorts and take them off, taking my thong with them in the process. He gave the cage a kiss which surprised me, the moisture of his kiss adding to the wetness of my own. He then did another thing that surprised me more, flipping me on to my stomach, taking out the butt plug that had lived there except for when Jenn was fucking me or when I was pleasuring myself, then he spread my ass cheeks and began to lick at my hole. I moaned loudly feeling his tongue on the outside of my hole, then darting in which caused an even louder moan, he ate my ass out for a long while before stopping to ask for the lube. I reached for the night stand and handed it to him.

He placed his body up against mine, whispering that he was about to enter me, I moaned and nodded, his head of his cock popping open up my hole. The walls of it settling around his meat. It was harder than the dildo, didn't have quite the same give to it, I did my best to relax as he pushed more of himself into me. It was my first time being fucked by a real cock and he was taking my virgin hole, if you could even still call it that after being fucked by a dildo so many times but still the was the real thing. He eventually bottomed out, his hips resting on top of my ass, he began to fuck me, slowly at first picking up pace as our bodies became entwined in the same motions. I looked back to him to see his face of pleasure, motioning for us to change positions.

He pulled out and I turned on to my back, placing a pillow under the small of my back, holding up my legs as he stood and put them on his shoulders, his cock then pressing back up against my hole and we were back to fucking. It felt amazing, having his cock buried deep inside of me, our moans almost matching, until almost in unison we both took deep breaths, I could feel his body tensing up again and mine starting to spasm, as we both came at the same time. My own cum coating my stomach and thighs, his cum filling my hole and down on to my ass cheeks. He collapsed on top of me, kissing me, letting himself go limp in my hole and slowly pulling out.

We embraced in one last kiss; I offered him to shower but he decided to get dressed and leave. I was sad to see him go but he had to leave for a hockey game, turns out I was right about my easier guess. I was just hoping that it wasn't him regretting his decision to have sex with me and running out the door. We exchanged phone numbers, this time me adding him to my contacts and then texting him, so he knew I was serious.

I looked at the clock, shit Jenn was going to be home soon. No time for a shower. I pulled my thong up my sticky thighs, feeling it make contact with the cum still slowly leaking out of my hole. I pulled on my shorts and then my tank top which stuck to my stomach. I made a quick dinner, just a salad topped with lots of veggies and nuts. It was okay but not the best thing I had made. She came home just as I was finishing. The look she gave me when she came in, told me she knew something was up. She walked over and took a smell of me, "you smell like sex slut." She said coldly but then the coldness turned into a laugh and a smile. I was confused about the quick change in tone. "It's okay, I know Tom was over here. He knew we are together and cleared everything with me before he came over. You should have texted me to check it out was okay but I guess you just wanted him so bad that you didn't even think about me.

"I'm sorry Jenn... he just came over and he looked so hot, was telling me that you had told him everything about me... and then it just happened."

"It's okay Stephanie. We've never really set up any boundaries in our relationship or said we were exclusive... and that's not what I want. At least I can go back to getting fucked now without having to worry about your reaction to it. So, this all worked out."

"What do you mean to back to? Have you not been hooking up when we aren't together... to be completely honest, I kind of assumed that you were since we weren't fucking."

"No, I haven't been with anyone other than you in the last month. To tell you the truth, I don't need be fucked often, fucking you gets me off nearly every time and you've become quite good at eating my pussy if I don't. So, I won't be hooking up much but you have my permission to hook up as much as you want and when you want, it would be better if you were getting paid as well but doing it out of passion is fine as well. As long as the sheets here are changed after." She pointed to the mess of the sheets which I just realized now had big cum stains on them. "Just if you fall in love with some guy, make sure to let me know, so I can hopefully recover from falling for you."

"Falling for me?"

"Yes, you idiot. Of course, I've fallen for you. You've spent the last 5 months becoming my ideal person. You've put up with my shit and all the shit I've put you through. I'm surprised that you are still here and with me to be perfectly honest."

"Well Jenn, I do really like you and like I said previously, even though some of the things you did were absolutely not okay, it got me to where I am today and given me a clear vision of where I want to go in life."

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This is likely the last chapter of this story. I hope you enjoyed and if you do want more, drop a comment, it will likely involve a significant time skip. However, I am open to suggestions and ideas where you would like to see Stephanie's story go.