Fantasies

Requested by Heather love :)

It was a simple question. An innocent question. A question one may wonder why it take so many years into a happy and balanced marriage for it to come up. And yet Sam feared the fateful moment when he would have had that conversation with his beloved wife Jennifer basically ever since they started dating. <<What’s your secret fantasy?>>

He knew he could not have possibly revealed the truth to her. Nobody could have known! Sure, she was his wife and confident, and she had no qualms revealing him that she fantasized about having a threesome with another girl. But he knew his fantasy was much more… problematic, and that by telling the truth he may have risked to even doom his marriage. Maybe he could have come up with something generic and innocent, but he also felt so bad about lying to her. He could not do it. For how much longer could he have kept his true nature a secret? He needed to get it off his chest, no matter how extreme the consequences would have been. So he decided to be frank.

He told her everything, all the things that had been bugging him for countless years and made him feel like a weirdo. He confessed to Jennifer that he was into crossdressing, and that sometimes he wished he was a woman. It was hard, but it felt good to finally get it all out. And yet it didn’t feel nearly as good as the discovery that Jennifer was actually quite excited to hear that. She not only didn’t mind that, but she was willing to help him fulfill his fantasy, and suggested that he should have gone to work the next day wearing a pair of her panties. Sam was so excited. Not only had he finally confessed the secret that tormented him for almost all of his life, but starting the next day he would have even started leaving out his secret dreams. He was so happy, and so madly in love.

The next day, while Sam was at work, Jennifer went out shopping for all types of underwear for him to wear, and even for some special pills she had recently seen advertised. Sam had a blast while wearing those panties. He was so tense, so constantly nervous and worried somehow would have caught him. And yet it felt also so enticing, so incredibly thrilling, and as hours went by and he started to get used to it he also realized how comfortable they felt, and how pleasant the feeling of the lacy fabric was. That evening as soon as he got home, he and Jennifer both agreed to make it a regular thing, and got rid of all of Sam’s old underwear and replaced it with what Jennifer had bought. However Jennifer did not tell Sam about the pills right away. Instead she started to make him take them unconsciously, crumbling them and putting them in his meals.

With time Sam got more and more excited with what he was doing, and even started to up the ante at work by sometimes wearing a bra, or a blouse, or pantyhose, which he would keep hidden under baggy sweaters and pants, pushing his limit further and further. It didn’t take long before the pills started to take effect and transform his body, and soon he begun to fill his wife’s clothes with soft new curves. He obviously couldn’t help but notice those changes, and Jennifer eventually had to tell him the truth, that she had been secretly giving him the TG pill, and that his body was slowly transforming to better fit his desires. Sam was shocked and overturned by the news. He sure was quite intrigued by the perspective of changing into a woman, but that still seemed like a pretty extreme route to take, and that thought scared him more than he had imagined. And yet, as he felt his skin getting increasingly smoother and more sensitive, and started to notice small mounds of flesh filling the cups of his bras, and saw how much cuter and attractive his face was becoming, he decided to keep undergoing the treatment. No matter what the consequences would have been, he would have thought about that when the time would have come.

One day he forgot to wear his sweater at work while wearing a low cut blouse and a bra, but to his surprise nobody seemed to pay attention to it, and did not say anything about it. He was confused, but quite pleased. After all the TG pill was starting to get very popular, and it was not surprising that in almost every office there would have been someone taking it. From that day on he stopped trying to hide what he was wearing and his changing body, and started to go to work completely en femme, showing off his new body which would keep transforming and becoming more and more womanly. And after a while he decided with his spouse to take the final step and undergo a complete sex change, becoming fully a woman and taking the identity of Samantha.

Life was great. Finally her most desperate fantasy had become a reality, and despite that, her marriage didn’t seem to be hindered by her transformation, and both she and Jennifer had never been happier. Her joy made her just radiant with beauty, and she soon become a confident and successful young woman, finally comfortable in her skin, and everybody around her noticed that and started to give her attention. Men especially. One man specifically. Her boss. It didn’t take long before he started flirting with her, even going as far as grabbing her ass and teasing her. Samantha was pretty shocked, and even quite scared, but since she had never experienced that kind of attention before she was also kind of flattered by it, and even started to enjoy the way her boss would flirt with her.

One day he mentioned that there was a performance review coming up soon, and suggested what Sam could have done to get an excellent review. She was both excited and frightened by the offer. She could not deny that she had been waiting for a chance to have sex a woman for the first time for quite a while, but the possibility also was quite scary, and most importantly of all she had to first hear what her wife thought about it. She had been with her every step of the way, and she also promised herself she would have always been sincere with her, not wanting to hide anything from her after she helped her making her fantasy come true. So she revealed everything to Jennifer, and to her surprise she not only was ok with that, but even wanted to help her get the best performance review possible, and suggested to invite him over for dinner. Apparently Jennifer would have soon seen her fantasy come true as well, having a threesome with her husband-turned-wife and her boss.

Sam started off her sex life as a woman with a bang, riding her boss’s thick and throbbing cock while Jennifer guided her and helped her. It was the most incredible experience of her life, and even though she realized that from that day on she could not have possibly experienced such heights of pleasure with her wife alone, she felt her love for her had become even stronger. After that night she got a big raise from her boss, and life could not have possibly been better, until one day she started to notice something was wrong. She felt sick in the morning, her head would spin, and she had nearly constant nausea. She thought it was some kind of virus, unsurprisingly considering that Jennifer had started suffering of the same symptoms, but one evening when she got home from work she found her waiting for her with a shocked and frightened expression on her face, and holding something in her hand. It was a pregnancy test, and it was positive. Soon they realized that that fatal night they both got pregnant from their night of sex with Sam’s boss.

As he learned that he knocked up both of them, Sam’s boss moved away and was never heard from again. The two girls were on their own, and since that was going to be also Jennifer’s first child, that meant that the following months would have been a continuous discovery for both of them. However, although slightly scared, they were not worried about what was to come. They were happy to know they could always count on each other, and they knew they would have managed somehow. As long as they had each other, they knew they would have been happy.