Relation Feminization

Every boy or girl during growing up discovers many amazing facts about the human body. Like many boys, I discovered them as well at the moment when I masturbated for the very first time. I didn't know what was happening to my body back then, it felt very pleasurable, but that was it. I didn't imagine anything as I didn't watch porn, because I didn't know that something like that even exists. But the urge of feeling that pleasure again got stronger and stronger, as I kept touching myself that way.

A few months later, I discovered that I am getting more aroused when I am looking at women on tv, which were wearing skirts, pantyhose, and heels. The idea of a woman's legs in dark, semi-transparent fabric made my penis hard, which was the signal to touch myself again. Not long after that finding, with every pleasure time as I called it, a white fluid came out of my penis, which terrified me like hell. Since my mom was the only person which whom I could talk about that, I asked her what is happening to my body. She explained everything about birds and bees to me and told me that is healthy for a boy to do what I do, of course in a private space, which is home. She also told me not to push my boundaries, and that I shouldn't do it more than twice a day, which was more than enough for me.

One time, when I was in the bathroom, I saw my mom's pantyhose drying. They were in skin color, but as soon as I saw them, I felt blood filling the smallest vessels in my penis. I couldn't control myself and I touched them at the same moment when I touched myself. I loved the feeling of the fabric immediately, but my joy didn't last forever as I filled my pants with a white fluid, or as my mom said - with sperm.

Over the next years, my fascination with women and their underwear grew, as grew my knowledge about certain things. My mom explained a lot to me during these years, but the most I learned from movies made for an adult audience. Mom never explained the details of intercourse between man and woman, she never told me that woman can give a man pleasure by taking his penis in her mouth. Every time when I watched that movie I was fascinated by women who were so dedicated to the case of french love. It aroused me even more than vanilla intercourse, where the vagina was penetrated by the penis - it was erotic and nice, but fellatio looks much better in my opinion.

Watching porn movies, I have learned even more about women's underwear. There was a much better option than pantyhose, and they ended in the upper part of the thighs with a lace floral pattern, in most cases, they were attached to straps of a belt in a matching floral pattern. To match the outfit of an actress, the bra and panties were matching the garter belt and the stockings. I was in love. In the movies I was watching, the woman was always slightly older than the man, wearing the things I loved to watch, kneeling in front of a man and bobbing with her lips wrapped all around his penis. But the finish was even better when the man spread his sperm across the face of an actress, and some of it landed on parts of her clothes. They looked even more erotic, having marks of one and the only purpose they were used for - the sex.

Years passed, and I cultivated my dirty habit. Watching porn, admiring the outfits, fascinated about oral sex. Then, I hit nineteen and I met her. She was five feet and seven inches tall with jet black hair color. Hourglass figure and medium-sized boobs, wearing black pantyhose or stockings, sky-high heels, leather skirt, and makeup heavy enough to notice her from the other end of a hallway. Everything happened in the local grocery store, where I couldn't stop looking at her with my jaw wide open when she finally disappeared between the alleys. I was a little disappointed and started to buy the things from the list my mom gave me when I heard someone talking to me in a soft, but deep woman's voice. I turned around and I saw her - the high-heeled bombshell. Just now, when she was closer to me, I realized that she was older than me, maybe like four or five years.

"Hello boy. I couldn't help but notice that you are looking at me. Do I look funny or something?"

"N-no, ma'am." I said stuttering.

"Then why you are watching me?"

"I-I just..."

"Just what? I know boys like you. Growing up, puberty time, buzzing hormones. I bet you like what you see."

"W-well... Y-yes."

"'Yes' what? Why are you stuttering so much? Is this your thing? If not, just calm down, we are just talking."

"Y-yes. I mean Yes, I like what I see. And I stutter because I never saw such a beautiful woman."

"Oh, so you are sweet! I like sweet. You know, if you like, we can talk somewhere else. Somewhere where coffee is served."

"Wait, are you inviting me to a... date?"

"If you like, you can call it like that. By the way, my name is Monica."

"Kyle." I responded.

Then she just told me the address of the coffee house and said to finish my shopping. When I walked home, I couldn't believe that I have met someone like her and that someone talked to me and asked me on a date! I was in heaven. When we met again, we talked a lot, we realized that so many things we have in common, our age difference came out, and Monica told me that she is twenty-eight. That was almost ten years of difference, but it didn't bother any of us. We've agreed on a next date as we exchanged our phone numbers. Back at home again, I couldn't help myself and of course masturbate, with Monica in my imagination, touching the soft fabric of pantyhose in the bathroom.

On the next date, she was dressed as hot as on the day we met, and we went to nice coffee houses, bistros, bars, and the movies. Finally, she put her hand on my cheek, moved closer, and touched my lips, with her red glossy lips, penetrating my mouth with her tongue. After less than a minute, she stopped and looked at me.

"You never kissed a woman before?"

"No... Sorry for that."

"Don't be sorry for lack of experience honey. I will teach you how to kiss next time we will see each other."

After a goodbye kiss, I went home. In the following weeks, I found a paid internship in one accounting company, so I could earn my own money and invite Monica for a drink because I was ashamed that she always pays for our dates. But I was determined. I wanted to impress her, I wanted her to teach me how to kiss. I wanted to do with her all the things that people do in porn movies. I wanted her. Our next date was pretty much the same as the previous one, but we were sitting in the silent, dark corner of the bistro, and she moved closer to me. I knew what is going to happen, and I didn't want to let her down.

"Nervous?"

"Yeah."

"Don't be. It's just a kiss. Follow my lead and do the same. You will be good."

And I did. I followed her instructions and we both kissed deeply, penetrating each other mouths. When we finally broke our kiss, her lipstick was ruined and part of it was left on my lips too.

"Someone got aroused!" She softly said, pointing at my trousers. It was a fact, that my penis was rock hard at this moment and I couldn't hide it.

"It's hard not to get aroused around you," I said.

"Feeling flirty, don't you?" She kissed me quickly again. "But first you need to know how to kiss your woman in a good way, then... Then we will see."

I smiled at her, paid for the tab, and walked her home. Monica lived in a relatively small house in a very calm neighborhood. Few yards of grass in front, few yards on the back of the house - nothing fancy, I would say it's an ordinary house. When we were close to the door, she kissed me on the lips again and said goodnight.

The following days were the same. I was improving my skills as an intern in an accounting company. In the department, I was the only guy, and the rest were seven women in their late thirties or early forties. They treated me very well, in fact - I felt like a raisin in a fruit salad. The payment was good too, and my manager already was talking about signing a contract with me.

Dating with Monica went great as well. We saw each other at least every second day and we went somewhere or we stayed at her home to fondle. This day was meant to be like any other day, but I felt in my guts that something was different.

"You finally kiss good Kyle. I like your style." She softly said.

"Thank you. I had the best teacher I could imagine."

"Yes, you had. But I think it's time for something more than kissing."

"Really? Like what?"

"I love your innocence, Kyle."

Monica kissed me and stood up. She slowly moved the straps of her black cocktail dress to the sides, which made the dress fall down to her ankles. Doing that, she revealed the hottest underwear that I could see.

Black bra with floral pattern and strong lace trim just above the cups, which decorated her beautiful breasts, matching lace panties and garter belt with attached nude stockings with high lace tops and black seam on the back. To finish the look, she was wearing black leather platform heels with red soles. She was a bombshell, and I couldn't help myself to stand next to her and start adoring her look with my hands.

"Do you like it?"

"I love it, Monica. You look outrageously hot!"

"You told me one time, that when you watched porn, you paid attention to this kind of outfit on actresses. I wanted to surprise you with that."

"Oh and you did..."

"Maybe you will surprise me now?"

"But how? I'm not dressed equally hot!"

"Just drop your pants lover-boy!"

And I did. My dick was harder than ever, and Monica immediately took it in her hand.

"Look like it's almost six inches. Not bad, not bad. Let's see what it can do."

And she dropped down on her knees. Her pouty red lips wrapped around my penis in no time, giving me a sensation that I never felt before. Suddenly she stopped, leaving a red mark of her lipstick on it, as she stood up and turned around. She whispered to me: "Unlock my bra" and I did, freeing her beautiful tits, but also noticing the marks of the bra on her shoulders and back.

"Are you okay wearing this bra? I can see the marks on your skin."

"Yeah, it's very comfortable."

"It doesn't look like it."

"Trust me, it is. Let's not talk about bra marks on my skin now."

She dropped to her knees again and sucked my penis for a few seconds, then she moved on all fours to the bed, moving her black lace panties to the side, revealing already soaking wet pussy.

"Come here, darling. Push that magic stick inside me!"

I didn't hesitate, and my whole penis slid in easily. Her warm pussy made me cum in seconds, filling her hole with my white, sticky sperm.

"You came? Already?"

"Y-yes... Sorry, Monica, I didn't want to finish so quickly... But it was my first time, and..."

"Oh, don't worry babe. I hope your fingers are working..."

She grabbed my hand and guided it to her sperm-filled pussy. I honestly didn't know what to do, but luckily for me, Monica guided me to the right spot and showed me what moves I should do. In a short while, she started moaning and eventually she reached the climax, collapsing and hugging me. I hugged her back and kissed her deeply when she slowly removed my hand from her pussy. When I looked at it, hers and mine juices mixed up, making incredibly sticky goo on the palm of my hand. It looked disgusting and hot at the same time. "Don't worry babe, we will work on your stamina," Monica said, and she started kissing me. Soon after that, we both fell asleep.

We woke up an hour later, the goo on my hand dried out, but we both needed to take a shower. Monica suggested, that we can do it together, as she has a shower cabin big enough for two people. After the shower, I had to go home, and the rest of the evening I spent in front of a computer, watching porn for educational purposes. The vanilla sex, fingering, and oral sex man to woman. This excited me enough to masturbate and then I went to bed.

The next few days were the same as before. Unfortunately, I could only text Monica since she was on some kind of business trip related to her job in the Human Resources department of a big corporation. Eventually, the weekend came, and I knew Monica was back at home. We texted each other and decided to get breakfast in one milky bar. I didn't wait for her too long, but when she finally came, she looked like million dollars. White sundress, matching heels, legs covered in nylon fabric, some jewelry, and light makeup. She sat down in front of me and guided my hand to her thigh, where I found lace on top of the stocking with an attached garter belt. My dick came to live in a second, as I kept caressing her leg.

"Hold your horses' babe! Let's eat some breakfast first."

I stopped caressing her leg, as she checked if my dick was hard again. We ordered some scrambled eggs with bacon and started eating.

"You know Kyle, I am still thinking about the moment when you asked me about marks of the bra on my back."

"Yeah, what about them?"

"Back then you seemed to not believe that it's not hurting me and it's pretty comfortable."

"Yeah, and I still think it's hurting you a bit."

"That's what I thought you might say, and that's why I have this crazy idea."

"What is it?"

"I thought a lot about it, and I think that there is an option when you can fully realize the bra is not hurting at all."

"Okay, but what is the option?"

"You just have to wear a bra."

"WHAT?!"

"Look, it will be only in my house, and I have already made an appointment with a local bra-fitter. The clerk is very, very discreet."

"You can't be serious right now."

"But I am! Besides, that can be our kinky thing. I would love to see you in a bra. Would you do that for me?"

"But it's feminine! And I am not gay or something!"

"Yeah, it's feminine, but not gay at all! You told me how you like girls wearing lace lingerie, you showed me how you admire me wearing it. Don't you want to try wearing it by yourself?"

"I don't know... It looks great on you, but on me?"

"You will look amazing, trust me! You have a light frame, you are not muscular, it will fit you perfectly! Let's eat and we will go to the bra-fitter."

"Oh-okay. If my beautiful girlfriend wants it, I will provide it."

"That's what I wanted to hear Kyle!"

Soon after breakfast, we walked down the alley to the bra-fitter. Finally, we reached it, and it was a small local lingerie store named 'Rebecca's'. Monica entered first, and I followed.

"Good morning. How can I help you?" The blonde clerk asked.

"Hi, we had an appointment for 10:00 AM."

"Oh, I see. Let's go to the fitting room at the back of the store. By the way, my name is Rebecca."

And that's how we've met the owner of the store, which was a bra-fitter too. But I think it's typical for stores like that. Rebecca closed the main door and we followed her to the fitting room at the back of the store.

"So, Monica told me that you want to try on a bra?" Rebecca asked.

"Well, to be precise..."

"Marvelous! I always admire guys with minds open enough to explore their feminine side. Please strip down, I want to see your naked chest."

With my red face, I looked at Monica first. She nodded, and I stripped down to my underwear. Rebecca measured my chest and my shoulders and went to the storage room. She came back with a blue lace bra.

"This is A cup bra. For a flat chest like yours, you don't need anything bigger. Put your hands in front of you please." When I did, she slid the bra on my shoulders and quickly locked the clasps on my back. With a little adjustment of the straps on my shoulders, the brasserie was perfectly fitted on my chest. "You don't much hair on the chest, but I recommend shaving it completely. You will look much better without it" the clerk stated.

"We will take it!" Monica said loudly.

"Splendid!" Rebecca responded. "I invite you to the checkout."

While both women went to the register, I started to take the bra off. "Leave it on honey!" I heard. I didn't want to make Monica upset, so I left it on my chest and covered it with my black t-shirt. The cups of the bra made two little bulges on my chest quite visible, but I didn't have any time to say anything, as Monica paid for it, grabbed my hand and we went to her place.

"Tell me, baby, is it uncomfortable?" Monica asked me, taking off my t-shirt, revealing my flat chest covered in the blue lace of the bra.

"In fact... no." I responded.

"I told you so. The marks are a normal thing when you wear a bra. What do you think about wearing it for the whole week?"

"I... I don't know..." When I finished saying that, Monica was already pulling out my hard penis.

"How about now?"

"M-Monica... Look..." I couldn't finish my sentence, because she started sucking my dick like crazy. I was on the edge of orgasm after a few seconds, but she stopped.

"I think you like it. You like when I'm sucking your dick when you are wearing a bra. Just admit it."

I couldn't help myself as I couldn't hold it longer. My dick started shooting sperm across Monica's face, but she immediately took it between her glossy red lips. It felt like she was sucking out the life of my penis. I never had such a strong orgasm before. When she finally swallowed the mess I made in her mouth, she said:

"I think you like it as much as I do. If you will wear the bra, you will get your rewards. Take it off and all you will get from me is a little kiss on your cheek. So, do we have the deal?"

"W...We..."

"Great! Now I would like to follow Rebecca's advice and shave your chest completely."

I couldn't say no. It was the only girl that was interested in me and I didn't want to lose her. So I have agreed to a bra and I have agreed to shave my chest. Of course, during the shaving, a lot of the shaving foam landed on the rest of my body, and when I rinsed myself with water, I realized that I have hairless patches on my belly, forearms, and legs.

"Oh my gosh, we can't leave you like that. You look hilarious! I have a better idea!"

And she shaved my whole body, completely. Then, I couldn't protest when she started applying a lotion, as my dick sprung back to life again. Monica grabbed it and led me to her bedroom, where she helped me to put on back the bra.

"You know... When I paid for the bra, Rebecca gave me the rest of the set, which was matching panties. And since when I looked at them, I'm dying to put them on you."

"What? Panties too?"

"Yep. Put it on and move them to the side. You don't need to take them off when you will fuck me."

When I slowly slid on the panties, the sensation was unspeakable. The soft material and the look of the lace covering my swollen member just made my heart pump more blood to it, making it even harder. Monica moved her panties to the side again and instructed me to do the same. Now, with her legs up in the air, I entered her juicy pussy without any problems. I was afraid, that I will finish too soon as the last time, but I've managed to start thrusting in and out, making the fabric of our lace panties touch. Looking at her face and hearing her soft moaning, I was sure that my dick was giving her some pleasure.

Unfortunately, when I pulled out a little, my orgasm came and I sprayed the entrance of Monica's pussy with my semen, leaving her without orgasm once again. She managed to quickly grab my hand and guide it to cream-covered pussy. The only thing she said was "Don't stop now, I'm close" and with the knowledge gained from the movies, I gave her an incredible climax. When she finally regained her senses, she took my goo-covered fingers, and licked them clean, leaving a small mark of the lipstick on them, but to my surprise she came closer to me and started to kiss me very deeply, sharing with me the mixed juices. When kissing ended, she looked me in the eyes and stated: