Chapter 8

(Two years transitioned )

With my second anniversary just having passed since I came home, I went out with Andy and Leslie and celebrated. They called it a celebration, but I didn’t see what the big deal was. To me, that part of my life was long over now. I got rid of nearly everything from then, and what I didn’t trash or donate, I packed away. My house resembled my current life, personality, and feelings, and that was all I needed. I understood that Andy and Leslie were happy for me, though, so I went along with it. Alice came with us too, who turned out to be a great fit with Andy.

Halfway through dinner, the restaurant staff came around to our table and began to sing happy birthday. It confused me, so I figured they had the wrong table or something. When the staff finished, everyone explained that they would consider this my birthday now as when I was born into Jenny.

“Yall are gonna make me cry,” I said, putting my hands up to my eyes to keep tears from falling.

“We also got you a present,” Andy said, then handed me a square wrapped gift, which seemed to be a picture frame.

“I can’t believe you guys,” I said, after opening it.

It was a framed novelty birth certificate with my birthdate being two years ago and having my name Jenny. I gave each of them a hug and a kiss on the cheek, starting with Andy, then Alice, and ending with Leslie. It was a fantastic night and much needed since I spent long periods focusing on work. When the check came, no one would let me pay since it was my ‘birthday.’

After dinner, Leslie and I went to the gym for a late-night workout session. We picked up a membership nearly a year ago and were going four days a week. Leslie roped me into signing up because she wanted to stay fit for her camming job. I didn’t have a particular goal in going to the gym as she did, but with the physical trainer she had paid for, I got into good shape. We worked out for a couple of hours, and I took a selfie when we finished, as always. I posted it to my social media too, which now had thousands of followers.

It was quiet when I arrived home. It had been quite some time since I moved back into the house after my parents left it to me, and I was still living alone. My salary allowed me to pay for everything comfortably, which stalled my plans for finding a roommate. Even so, I found particular enjoyment in living alone and coming home to a quiet place every day.

With my new birthday having been celebrated, it was fitting that I was scheduled for my last checkup involving my transition. In the morning, I prepared for it with a thorough shower, then dressed for work since I planned to head in afterward. The checkup followed the same procedure as all the previous. I had my eyes checked, my ears, voice, reflexes, and so on.

Afterward, I undressed for a more intimate examination. Every bit of my breasts was checked, followed by a speculum being inserted into me. When they finished, I got up so they could take my measurements, which was usually the last step of the examination. The good news was that they hadn’t changed, which also meant my breasts probably weren’t going to get any bigger, and that made me happy. It was difficult being a thin girl with big boobs and finding tops that fit well, that also fit my boobs. Luckily, I was recommended a site that did custom shirts, which I used to buy shirts for work.

“Alright, Jen, this actually completes our evaluation. Your vitals have been consistent, and there isn’t anything to show future problems as a result of the transition. Even so, you’re still the first person to ever go through this, so if anything feels off or strange, definitely contact us.”

“I will certainly do so,” I answered, smiling.

(My boss)

A week later, my job put together a banquet to give out annual awards. We rented out a catering ballroom space, provided food, music, and even drinks. Employee of the year recognitions was given to staff from different areas of the company. It was a formal event, and I had to present a few of the awards myself. Anticipating the event, I had gotten my hair done, along with my nails, and bought a new, black dress.

When my turn came to hand out awards, I stood behind the podium and looked at all the people seated at their tables. I was nervous up until this point. I expected to be even more once I got up in front of everyone, but my professional persona kicked in, and I just started. I had three people in my district that I wanted to give awards to for exceptional service. I called them up one at a time to provide them with a certificate and gift card, then had a photo taken.

My district manager, Mike, took the podium after I finished. He was the same manager who tried to coerce me into sex before I got the promotion. That memory was always present in my mind when seeing him. It didn’t make me mad or angry. Instead, I remembered how it made me storm into his office a few days later, after finding my courage. He flirted with me often since then but never tried anything else.

By the time I got comfortable in my seat again, Mike had called my name on the microphone. To my surprise, he was awarding me as a manager of the year. Just as I had done with the others, he handed me a certificate, and I gave him a hug. I smiled and blushed on the way back to my seat.

After the formalities were over, everyone was able to have dessert, drink, and dance. As for me, I stayed at the table and had a few drinks, while mostly keeping to myself. Eventually, Mike came over and invited me to dance. Perhaps it was because he had awarded me or because I was a little tipsy, but I accepted. Even though I wasn’t the best dancer, I think I did alright, or that could’ve been the alcohol thinking too.

When the function finally came to an end, I waited until everyone exited before leaving myself. I got into my car and sat there for a moment, making sure I was okay to drive. I didn’t feel dizzy or lightheaded, so I turned the key and nothing. The car didn’t start, nor was there any sound to it at all. I tried several more times before falling back against the seat, wondering what to do next. Since this was the company’s car, I called the hotline for it and explained the situation. By the time I finished on the phone, I could see Mike walking over to me.

“Everything alright?” he asked.

“The car won’t start,” I answered with a sigh. “They’re sending a tow truck.”

“These cars always seem to have battery issues,” he said. “Well, when the tow truck comes, I can give you a ride home if you want.”

“Yeah, I would appreciate that,” I said.

It felt a little weird to be alone with him in the dark of night, but at the same time, I was glad he was there. I got out of the car, and we stood there and talked for a while.

“You did a wonderful job tonight, as always,” he complimented.

“Thank you,” I said, smiling, though I had no idea he thought so highly of me.

“I never sincerely apologized about what happened in my office,” he suddenly said. “I’ve used my position to take advantage of women, and you were the first to stand up to me.”

“I accept your apology,” I said when he paused. I never expected to receive one, and I had gotten over it.

“Thank you. But, if you’ll let me get a little more off my chest, I would be grateful.” I nodded. “I can apologize for years, but I know this will probably all catch up to me sooner or later. I’ll be fired, or arrested, or both. And, even though I regret much of what I did now, I still feel the urge to keep doing it. There’s something about a woman doing whatever it takes that turns me on. Even as I walked over here, I thought about asking for a sexual favor.” He went silent and shook his head.

“I won’t speak for anyone else, but you did cross a line with me back then. You did stop, though, which I suppose is the reason why I was able to move on from it.” I said.

The tow truck arrived and interrupted the moment. After my car was hooked up and pulled away, I got into Mike’s car. We sat in silence all the way to my house. I suppose he was thinking about what I thought of him now. I did think about that for a minute. My thoughts went back to the day he tried to force himself on me. Even tonight, he looked at me with lust in his eyes. I wondered if he knew how obvious it was that he kept looking down at my body. As we pulled up in front of my house, I realized how horny I was and how long it had been since I last had sex. Mike was twice my age, at least, probably more. Still, he didn’t look bad, and he always dressed nice and smelled good.

“Would you like to come in?” I asked. “I can make some coffee or something.”

“Thank you for offering, but it probably isn’t a good idea. I’m sure you know what’s on my mind right now,” he answered. I could see his eyes look down at my body again.

“It’s up to you,” I said again as I exited the car.

I walked up to the house and turned to look back when I reached the door. I assumed since he hadn’t parked the car correctly yet, that he wasn’t going to take my offer, so I went inside. I started looking for a place to put my award until there was a knock on the door. I checked the peephole, even though I knew it could only be one person. What I didn’t expect was for him to step inside, pull me toward him, and kiss me.

He kicked the door closed as we moved in further, with me in his firm hold. It happened fast. Once we reached the sofa, he turned me around and pulled my dress up before then pulling down my panties, which fell around my ankles as I stood in my high heels. My mind raced, knowing what was about to happen, questioning if this is what I really wanted, and if I would regret it. His hand landed on my left hip, then I felt the tip of his cock press against my womanhood. With a light push, it went inside of me, sinking into my depths. His body pulled back, then came rushing forward to slam into me, which made me moan out loud. He pushed me over the sofa more as he repeated this several more times before finding a rhythm.

I couldn’t believe I was having sex with someone so much older than me. It felt good, though. His hands moved up my sides, then pulled the top part of my dress down to gain access to my breasts. His hips continued to plow me from behind while his hands grabbed my tits.

“Fuck, Jen!” He grunted. “You’re the youngest girl I’ve ever been with, and the sexiest too.”

My hands braced the arm of the sofa as I felt him drive his cock into me over and over. I could feel his hands firmly squeezing my breasts and holding them for leverage. My dimly lit, quiet living room was now filled with the sound of me being fucked by my boss. The longer it went on, the more I knew I was going to regret it. Right now, it didn’t matter, he wanted to fuck me, and I wanted it to happen.

He didn’t stop or change position. It was like a lust-filled drive to fuck me as hard and as fast as he could. His hands moved from my breasts to my shoulders, holding and pulling me, while his hips slammed me from behind. For an older man, he had good stamina and vigor. Eventually, he grunted, then shoved himself deeply and firmly inside of me as he came.

Almost just as quickly as it started, it was over. We fixed our clothes in silence while my mind thought about what just happened. I found my phone and set the alarm as a reminder to take a morning-after pill. This was already starting to feel awkward enough, so I didn’t want to increase that by ending up pregnant.

“I guess you can cross me off your list now,” I said.

“I wouldn’t put it like that,” he rebutted.

“I’m a big girl. I know what I was getting into,” I said.

Trying to prevent things from being too awkward, I went to make some coffee. As I stood there waiting for it to brew, I could feel his cum already seeping from me. I looked to make sure he was still in the living room, then quickly reach down to clean myself. After the machine finished, I carried a cup out to him and took a seat.

“You know, if you want, I can stay the night. I don’t want it to seem like I just came in for sex,” Mike said.

“You don’t have to stay,” I answered. “As I already said, I’m a big girl. I knew you wanted to have sex with me, and I chose to act on it. I don’t expect anything else. This was a one-time thing, so don’t expect it again,” I said, smiling.

“I respect that,” he said, smirking. “Forgive me in advance for trying.”

(Roommate)

It didn’t take long for the rumors to start about Mike and me. They were rampant for a few weeks and slowly died off just as with the other girls. I was just another girl that Mike had supposedly slept with now, but it didn’t bother me as much as I thought it would. Despite what anyone was to think, I made it clear with Mike that I didn’t want any rewards for having sex with him.

I told Leslie all about it when we finally got to have a girl’s night. We bought some snacks and drinks, then crashed at my house after the gym. After a few drinks, I recounted the entire thing, from the award ceremony all the way up to inviting him inside and having sex. Leslie loved every bit of the story, even getting up and asking exactly how it happened while posing over the couch in the same way he fucked me. She kept getting it wrong, so I finally got up and showed her. I bent over and placed my hands out in front of me.

“And you did that while in high heels? I’m impressed,” she said with a grin on her face.

“Yeah, he held me just like that,” I said.

“And, where did he finish?” She asked.

“Inside,” I answered.

“You let your boss cum in you?” Leslie asked, surprised.

“I was tipsy, and it all happened fast,” I explained.

“See, this is why you should get a boyfriend or at least a fuck buddy. Then, you won’t get horny enough to fuck your boss in the middle of the night,” she said, laughing some.

“I tried that last year, remember. I got with Alex a couple of times, then he kept demanding anal sex.”

“Whatever happened to him, anyway?” She asked.

“Not sure. The last time I was with him, he was mad because I wouldn’t do anal. After that, we just stopped talking. I wasn’t even into him that much, anyway.”

“Maybe you should try it sometime,” she suggested.

“I wasn’t even into it when I was a guy, so I don’t think I’d like it now.”

“You don’t have to like it. Just tolerate it long enough to for him to do it. Then, you’ll have a happy guy,” she said.

“I suppose,” I said, laughing some.

“So! Are you still looking for someone to move in with you?” She asked, changing the subject.

“I wouldn’t call it looking, per se,” I said. “Why?”

“Well, the lease on my apartment is up, and I want to move. It’s okay if you changed your mind, though,” she said.

“Oh, no, I think we can make that work,” I answered.

“Will you be okay with me doing my cam shows? I promise everything involving them will be kept in my room,” Leslie added.

“That’s fine. You can look at the room if you want, and of course, you’re free to use the rest of the house. We can talk about rent and stuff tomorrow if you want.”

It didn’t take long for Leslie to start moving her belongings in once we agreed on everything. By the end of the month, she finished moving in, and I gained a roommate. I missed the benefit of quiet and privacy right away, but she was always home, and she bought a lot of food and supplies for the house. As she promised, I barely even knew about her camming. Now and then, she came running down to the kitchen for a drink covered in lube, oil, or something. Which, I must admit, she did look good, though I didn’t get quite the same feeling as when I was a guy.

One night, Leslie came down wearing nothing but a robe while I was sitting in the living room. She picked up a bottle of water, then came and stood near me while she chugged it down. I was curious as to why she was always so thirsty just from being on a webcam. I pictured camming as just lying there and touching yourself.

“Why are you always so thirsty?” I finally asked.

“Messing around on cam for hours at a time and having like ten orgasms will do that to you. Not to mention the lights beaming on me,” she answered.

“Ten orgasms?” I said, surprised.

“Well, I think I’m up to eight tonight, but, yeah,” she said. “Don’t tell me you’ve never done it.”

“I mean, I’ve heard girls can do it, but no, I never tried that many.”

“You should. You have to suffer through a period every month, so you might as well enjoy the upside of being a girl, too.”

“Maybe,” I said. “And, before you ask, no, I still don’t want to get on cam.”

“Of course you don’t,” she said, laughing. “I gotta go get the show back on, so have fun.

As Leslie scampered back to her room, the thought of orgasms was still on my mind. She was right about me not utilizing the full potential of being a female in that regard. I went up to my room and got comfortable in bed with my laptop. Just like the old days, I put one hand below and used the other to search for porn. It had been a long time since I last watched porn. Because I wanted to try and cum a bunch of times, I went for one of my favorite blowjobs videos. The feeling was quite different since I didn’t have a dick anymore, and hadn’t had one in years. In moments, I pictured doing the sucking rather than being sucked. I imagined how hard he was, how much I could take in my mouth, and how it would feel if he were inside me.

It worked well too. My fingers moved down from my clit, then pushed into my wet slit. I drove them back and forth, progressively getting faster as I warmed up. With my left hand, I continued to browse for videos. After a few minutes, I remembered that I wanted to go for several orgasms, so taking my time wasn’t going to get me there. I left the current video on, then moved my hand down to rub my clit while the fingers on my other hand still pumped in and out. It was really hard for me to orgasm without using my clit.

I built myself up and finally reached my first orgasm, then paused briefly while I enjoyed the warm tingling all over me. My second orgasm happened a few minutes later, followed by a third after almost the same amount of time, and a fourth after that. From the first to the fouth, it took about fifteen minutes. With just four, I already felt tired, but I didn’t need anymore since I confirmed I could have multiple in one session. I got up to clean myself and could still hear the faint sound of Leslie’s show going on. It was hard to believe she could be on camera for so long in front of people.

(Clubbing)

For Leslie’s birthday, we both went to a club, even though it wasn’t really my thing. It did give me a reason to wear some clothes that I hadn’t had a chance to wear yet. I had a new dress and heels that I had bought, but they weren’t appropriate for work. Not long after we arrived, we started drawing the attention of guys. Leslie, of course, was looking for that, and it didn’t take long before she was off dancing.

I turned down the first couple of approaches, unsure if I even wanted to join in at all. Skylar had been on my mind lately, even though I hadn’t seen or spoken to him since we split. It was probably the reason I never pursued another relationship too. Skylar treated me well, and I threw it away because I was scared and tried to pick my best friend for comfort.

Eventually, another guy came over to talk to me. Leslie was still dancing, and because I didn’t want to be a killjoy, I followed him onto the dance floor. We spoke long enough to find out each other’s names and ages while we casually danced. His name was Jamie, who was also celebrating his birthday today, having just turned eighteen. Even though having a younger partner felt okay when I was a guy, it somehow felt weird to be a woman with a younger guy.

Jamie’s age didn’t stop him from getting comfortable with me. His hands dropped down, and very purposely landed on my butt. For now, I went along with it, turning to the beat of the music until I ended up grinding against him. The music and dancing were a good distraction, which allowed me to start having fun. After a few songs, Jamie bought me a drink. It was only a soda, but his gesture was nice.

“So, did you come to a club by yourself on your birthday?” I asked.

“No, I actually came with a couple friends, but they’re over there drinking somewhere,” Jamie said.

“Some friends you have there,” I said, smiling.

“Eh, it’s okay. They can get drunk and be dumb while I get to talk to a pretty girl,” he said.

“Mm, thank you,” I said, unable to stop myself from blushing.

“Do you hang out here a lot?” He asked.

“This is actually my first time here,” I answered. “I don’t usually like clubs. What about you?”

“Second time for me, but first time at this one. My friends only brought me here so they could drink,” he said.

“Hopefully, you got to at least do something you wanted today,” I said.

“There wasn’t much I wanted until I saw you. Now I’ve just wanted to kiss you,” he said with a laugh.

“You want to kiss me, huh? This all sounds like a scheme to hook up with me,” I said, then smirked.