tagTranssexuals & CrossdressersMy Bizarre Life Change Ch. 03-04

My Bizarre Life Change Ch. 03-04


Chapter 03

It had been a little over six months since my wife left a note stating she was leaving me for another woman and my next door neighbor agreed to help me win her back. Although that required me to follow her directions to the tee which included feminizing me and introducing me to gay sex with her husband. I know it all sounds so bizarre and crazy but at the time I was so distraught I would agree to anything to get my wife Denise back.

Little by little, Cynthia, my neighbor, began to get me more and more accustomed to my feminization. She had begun by instructing me to have sex with her husband Frank and to take her dildos, strapons, plugs, and his cock up my ass. She began replacing my wardrobe with female undergarments and started me on a hormone treatment that included testosterone inhibitors and female estrogen. Within weeks my facial hair slowed and I began to add some padding around the hips, ass, and chest. My nipples became darker and swollen and much more sensitive as the breast themselves started to grow.

Cynthia wanted my nipples to be much more prominent so she trained them several times a week by using a pump that sucked on my nipples through a tube, pulling them out. Then she and Frank would spend an enormous amount of time pulling, twisting and sucking on them. Cynthia had me wear panties and a bra under my work clothes which required me to wear heavy oversized shirts to keep my attire hidden from my staff at work.

The downside to the hormone therapy, besides my testicles which seemed to shrink, was my loss of libido. I just didn't have the sex drive I previously enjoyed. I still made love to Frank, sucking his cock and allowing him to fuck my ass and I often went down on Cynthia. But I just didn't really care about sex any more and certainly never instigated it.

Cynthia was best friends with a sexual therapist who advised her to back off the testosterone inhibitors and to begin using crèmes and natural supplements which had less of an impact on my sex drive. The therapist gave her pills which greatly enhanced my lagging libido and soon I felt myself in an almost a habitual state of arousal. Cynthia was satisfied with my breast development and size which now completely filled an "A" cup and felt the new treatment would be a good balance.

The therapist added one more element to my regimen which included psychotherapy. While I had not resisted Cynthia as she physically altered my appearance, I think she knew deep down how ashamed and uncomfortable I still felt about what I had become. I was resigned to what she was doing and totally submitted myself to her but embracing it was another matter entirely. Cynthia's friend Jean created a website that I was instructed to view for half an hour each day.

The website was loaded with literally hundreds of images of preoperative transsexuals, lesbians, and gay men in a variety of sexual acts. There were women making love to women, men sucking and fucking other men, and men and women having sex with she males. The images flashed up just long enough for it to register before the next image filled the screen. Several in just a second. These subliminal messages were intended both to make my mind more acceptive to the activity as well as drive me to state of sexual frenzy.

Cynthia had prohibited me from masturbation although I was encouraged to stimulate my nipples and to engage in any anal stimulation with vibrators and plugs. I found that I could cum just as easily and sometimes more intensely by massaging my prostrate with a vibrator while pulling on my nipples which were now about an inch and a half long. After one of the therapy sessions, I would beg Frank to let me suck him or to take my ass which I had begun to refer to as my pussy per Cynthia's instructions. Just as often, I would have oral sex with Cynthia and she would fuck me with one of her strapons which were always bigger than Frank's cock.

It wasn't lost on me that Cynthia never had sex with me in front of Frank, although Frank and I would often do so in her presence. It was commonplace for me to go down on Frank while the three of us were watching television or to begin kissing, which always led to Frank sucking on my tits in front of his wife. Perhaps more peculiar, I could not recount a single instance in the six months of living with them that I had ever seen Frank and Cynthia make love.

Sure they had kissed, but even when he came from their bedroom, there was never any sound or evidence that the two had ever engaged in sex. One morning after Frank and I had made love, his cock still buried in my pussy, I asked him about it.

"Frank, can I ask you something," I inquired.

"Sure babe," he responded as he moved his chest into my back, dropping his arm over my waist, reaching around and holding my own little cock.

"I never see you and Cynthia together. I mean really together...having sex," I paused. "Are you two intimate. I mean, its okay with me. I would only assume you are. She's your wife. I just never see the two of you...doing it."

Frank was quiet. There seemed to be a little tension. Something I had not quite expected. Then his soft voice broke the silence.

"I kind of thought you knew. Cynthia is a lesbian. Always has been," he said back with emphasis on the last the words.

"Even when you married her," I replied back as I twisted my head back, trying to look back at him.

"Yea, we met in college. I was taking a sociology course and I saw her across the room. She was the most gorgeous girl I had ever seen. We struck up a conversation and then I saw her in the lounge, library, and café. Each time we found we enjoyed each other's company and began studying together. It wasn't long though before I asked her out and she was honest with me telling me she was strictly a lesbian."

"While I was crushed, we kept seeing each other socially, attending things together and then even going on dates. We just didn't have sex. At first she took pity on me and jacked me off. Then little by little she encouraged me to cum for her and it seemed after the moment had passed, we both went on having a great time together, Frank continued.

"I knew she had relationships on campus with other women but she never rubbed it in my face and it was Cynthia who first brought home a guy she knew who was bisexual that sucked my cock and let me fuck him. Pretty soon, she had a variety of these men and it became something that I appreciated. She sort of took care of both of us," he went on.

"At first the thought of reciprocating was the last thing I thought I would do, but Cynthia encouraged me to experiment, give it a try. After a while, I found that I enjoyed it and I became pretty much a bisexual. I prefer women to men but at the end of the day, I can go either way," he finished.

"But you really seem to enjoy being with me. Well, you're not exactly a guy now are you," he said as he tugged at my waist. The realization of what he said sent a shudder down me. "You're sort of both."

"Frank," I started and then stopped, trying to choose just the right words. "My wife....Denise said she left me for a woman. Is Cynthia that woman?"

The silence was stark as I felt his arm tighten, drawing me closer. I knew I hit a nerve. I knew the answer already.

"Did Cynthia do all this to me to help me get Denise back... or did she do this for you?" I could feel tears in my eyes thinking about what I had just said. Had I undergone all this, changing me from a man into a she male, thinking I was doing this to win back my wife, only to find Cynthia had other intentions.

I sat up in the bed as Frank called out my name. I ignored his plea to lie back down as I wrapped a robe around me and headed down to the hall where Cynthia was having her morning coffee.

"You're the woman my wife left me for," I said curtly from the doorway as Cynthia looked up and then calmly reach for her coffee cup drawing it to her lips.

"Yes. Yes I am," she replied back matter of factly. "Did Frank tell you that?"

"He didn't have to tell me. So, was all this for Frank? Was there never any real hope of Denise coming back to me?" I said feeling a tear rolling down my cheek. I wasn't sure if it was a tear of anger or sadness as the realization of it all hit me.

"No Erin (the name she used for me instead of Eric) , it was for all of us. I promised I could get her back and she's coming back. She'll still be a part of your life, my life too. You see, I love Denise as much as you. We love each other. But neither of us could leave you guys. I love Frank and will never leave him. Denise loves you but we know we need each other. If I would have suggested six months ago that you accept me as Denise's lesbian lover and Frank as yours, what would you have done?" she reasoned.

"Now we all have each other. Denise has already planned to come home this weekend. We will all be together. As a matter of fact, she's making arrangements to sell your house next door. Neither of you stay there anyway. We'll all live here...together."

"But, will she still be my wife," I struggled trying to get my hands around all this.

"Wife, husband...those are just labels. Denise and I are lesbians. We prefer to have sex with other women...and you, well you're not exactly all man now are you? It's the best of everything, you and I have Denise and Frank has you. It will all work out, don't you see?"

In a crazy way I did see her logic. She was right. There was no way I would have ever allowed our arrangement months ago but in a perverse way, it did make sense. I wanted Denise back and was willing to do anything to make that happen. Now she was coming home, our new home. One that included Frank and Cynthia. Looking at it now, I couldn't image anything I wanted more.

Chapter 04

It had been several months since I'd seen one of my buddies that I often hung around with. Matt and I had grown up together and while we went to different colleges, we had remained great friends. He was in my wedding and one of my few single buddies who had yet to tie the knot himself. We typically got together to shoot hoops, play tennis, or racquetball and so it wasn't a shock when he called and asked me for a game of racquetball after lunch.

I knew my appearance would be quite alarming to Matt with my longer hair and feminine features so I decided to prepare him by telling him I'd had a small bout of prostrate cancer. I was aware that men who have prostrate cancer are often prescribed estrogen which could explain my appearance.

"Look, I haven't made it public or anything but a few months ago, I had prostrate surgery," I explained.

"Are you okay?" he said with anxiety in his voice.

I hated lying to him but it was much preferable to the truth. "Yea, they got it all but I'm undergoing hormone treatment and they have me on estrogen," I explained.

"What's that?" he inquired.

"Well it's a hormone women produce and it manages the testosterone levels in the body as I recover. But it has some bitching side effects," I explained setting up my story.

"Like what?" he inquired.

"Well, you'll see for yourself. Just don't give me any shit," I demanded. I hoped that might at least settle things as I changed in my office, slipping a sports bra on to secure my small breasts.

I informed Lynn and our receptionist Ann that I was headed out for a little R&R and would be back mid-afternoon.

Matt was indeed surprised but my preemptive work at least kept him from asking too many questions. He didn't want to offend me as I pointed out that estrogen did have the side effect of adding a little weight and perhaps rounding my features.

"Kind of letting your hair grow out too aren't ya'," he teased.

"I suppose that was me rebelling against all this shit," I shot back as we took our positions on the court.

More than a few times, I could feel his eyes examining my body, looking at the changes that were taking place. But he dropped any further discussion as we settled into our game.

I'm not sure if I can blame it on the hormones but my game had slowed considerable as Matt beat me unmercifully. We both acknowledged my recent surgery had likely impacted my performance. Although, there had really been no surgery. I was just that out of shape!

I took a shower at the fitness center in a private stall, careful not to let anyone see my body that was transitioning between male and female. I slipped on some sweats and headed back to my office to actually change into my clothes I had on earlier in the day. As I walked through the office, Ann, our receptionist seemed to be out and Lynn was in her office on the phone. Lynn was my marketing representative. She was a very pretty 23-year old that I interviewed after she graduated college.

Lynn was a natural at sales and would bring the business in for me to develop the software that she in turn trained their employees on. The job was intense as it required a great deal of travel. She was a single girl and we kept her bouncing from city to city. I knew I was extremely fortunate to have someone of her skills and business savvy as well as striking good looks.

I closed the door and locked it behind me as I quickly slipped off my shoes and pulled off the sweats. I eased a pair of yellow thong panties up my legs and was just fastening the matching bra set when Lynn knocked on my door. It startled me and I yelled out just a minute when her voice broke the silence of my office and sent my blood rushing as I heard her utter my name.


I could have sworn I turned the lock on the door but apparently in my haste to dress, I must not have done so as I turned to see Lynn peering from around the door. My arms flew up trying to cover my chest as my right hand plunged in front of my crotch. Lynn's eyes grew wide but rather than slam the door back shut, she eased on in my office, all the time her eyes surveying my semi-nude frame dressed only in the skimpy panties and bra.

"Eric?" she said again but his time much more a question than the previous which signaled her entrance. It was a terribly awkward moment as I struggled for just what to say as she closed the door and seemed to back up against it. All the time, her eyes roaming up and down my body.

"Lynn, I can explain," I began stammering. "My wife and I, we made a bet, and this is, well, it's not what it seems." Each utterance, each explanation was falling flat as I tried to think how I explain myself.

"Oh my heavens. Holy shit," she uttered as she surveyed the scene in front of her. "So you have been dressing as a woman. I thought months ago, I saw a bra under your shirt but I dismissed it. But you are..."

"Lynn, please let me explain," I started but unsure exactly what to say next.

"It's okay Eric. I'm not here to judge you. It's just, well its not everyday you find out your boss is into dressing up as a woman," she said smartly now catching her breath as she began walking toward me, her eyes still trailing up and down my body which was now on full inspection as I still stood with my arms trying to cover my strategic places.

"So, you want to tell me the truth," she asked.

I finally dropped my arms and then began to relay a little of how this all came to be. While I didn't go into all the details, I told her most of the story.

"You've got real tits," she exclaimed. Those are real," she said as her eyes fell to my chest. Her gaze fell to my feet and I could tell she was examining my freshly painted nails.

"So," Lynn began, "Just who knows about this?"

"My neighbors, Cynthia & Frank, my wife of course, and a few ladies down at Cynthia's spa," I replied.

"And that's it?" Lynn shot back. "Pretty tight circle...and me. But I can keep secrets. I can do that for you. Thing is, what are you going to do for me," she stated as she continued to walk around me, gazing at my cheeks exposed by the thong I was wearing.

"What is it you want Lynn?" I asked back, knowing I had little room to barter.

"Well, first off, I've worked my butt off for you. I find the customer, sell them, deliver them, and then train them. I know this is your company, but I feel I'm more of a partner than an employee," she began.

"So you want money?" I asked.

"Not just money Eric. I mean a partnership. I believe I'm entitled to that. I mean what do you have without me? " she responded.

She had a point but I wasn't ready yet to start giving away a company that I had worked years to build. "So, twenty percent? Does that work for you?"

"Don't insult me Eric. I could ask for fifty-fifty. But I'd settle for 40," she said with emphasis on the 40.

"Are you kidding? 40%?"

"I think that's fair," Lynn responded back, "and in your position, perhaps more than fair."

She had a point and she really had significantly contributed to the success of our company.

"Okay. I'll do that," I agreed in resignation.

"And then there's Ann," she kept on.

"What about her?" I asked.

"We need to take care of her too. She's my right hand and not to mention we need to keep her quiet. It's only a matter of time before she catches on like I did. I figure for ten grand, we can keep her happy and quiet," Lynn reasoned.

"Ten thousand on what she already makes?" I shot back.

"Damnit Eric. You...we," she corrected yourself, "can more than afford it. In spite of the recession, we've had a great year. I need her here on the ground keeping up with things. We're giving her a raise...effective today."

I looked at Lynn. She wasn't budging and quite honestly, Ann was a great employee. "Okay, give her a raise," I complied.

"Now, now we need to talk about us," Lynn smirked.

"Us?" I said back.

"Do you know what kind of social life I have?" Lynn asked waiting for some type of response. "None. I'm on the road all the time. I haven't been on a date in months. And all this time, you know, I've always had a bit of a crush on you."

"Lynn," I started to respond.

"No, be quiet. Let me finish. From the day you hired me, I've always thought you were the most attractive, sexiest man," I felt myself blush a bit as she relayed her feelings. "But every day when I came in, no matter how I tried to impress you, it was like beating my head against a wall."

"Lynn, I thought it best to keep things professional. Not to mention the fact I'm a married man," I stated back.

"Married? Professional? Look at you. Wearing women's under garments under your work clothes. Your nails painted. You have tits for heaven's sakes. And married? Your wife left you for a lesbian. You're having sex with her lesbian lover and her husband. I got all that right?" she stated more than inquired.

I hung my head listening not able to respond.

"Any of that wrong?" she said raising her voice. I simply shook my head back and forth.

"I didn't think so," she said as she moved toward me. "I'm dying to see what's under that top. Why don't you take that bra off for me," she directed.

I thought just a second, but knew we were too far down a road now. I suppose I should have been embarrassed and perhaps a part of me was. But I gathered from her tone she was more interested than curious.

I reached behind and undid the clasp as the straps fell around my shoulders and I removed the cups which surrounded my little "size a" tits.

Her eyes widened as she took in my breasts, the hard little nipples, contained behind the padded bra.

"Damn," was her one word reply. "Look at those. They're real. You have real tits. I've never seen anything like it," she raved. "And your nipples. They're so dark and long!"

I looked down myself to see my little mounds.

"Can I touch them?," she asked looking up at me and then back to my breasts.

"Go ahead," I replied back as her hand reached out, dropping softly on my left breast. Her fingers were so warm as they gently ran over the contours of my tit, tracing patterns over my nipple as she ran little circles around the aureoles.

Report Story

bywatchdwag© 15 comments/ 130949 views/ 40 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: