Pantyboy

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Crossdresser's first exploration.
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College was interesting. You meet people from-EVERYWHERE. Six months into my freshman year my roommate came home from a weekend visit to his parents. When he came back he had arrived with a bunch of magazines and newspapers. I looked through them with some interest. I was from a very rural almost uninformed town in the midwest and he was from what can only be described as "The Big City".

I was intrigued about what was going on in "The Big City" so I read voraciously. Everything. Even the personals. And -boom-right there was a personal that caught my eye.

"Want to be my pantyboy? We will go out when you are ready." And then the name Estella and a phone number.

I was just a little intrigued. I have been attempting to wear panties since I was at least 6. And even as I read this personal I was wearing panties. So why would I have to be a pantyboy when I was all ready. Clearly -to me at least - something else was going on.

After several days of pondering I decided I wanted-NO I needed-to call. The initial conversation was very awkward. And I think Estella was exasperated with me. Finally she fairly exploded, "You want to discuss this further -come to this address." She gave an address and city and hung up abruptly. I was not about to give up.

The address she gave was very close to "The Big City". When I rolled up I was shocked how suburban the area was. People going to work, joggers, white picket fences, children playing. I went to the house number indicated and knocked.

A small woman answered. No more than 5 foot 2 inches. Maybe 100 pounds. Red hair. Nice body.

"Hmmmm. Is it you who called me??" Right to it. No introductions. No small talk. No nothing.

"Yes."

"Well, come on in. Let's hope you talk better in person than you do on the phone."

She gave me iced tea. We chatted. She asked a bunch of questions. Some relevant. Others I didn't see the point.

"OK," she finally said, "Let's get down to brass tacks."

I nodded.

"What I mean by pantyboy is someone like you." She paused and looked at me. "You are slight in build, nice legs, adorable butt, nice hair. Your eyes are a little small and beady but we can work with that. But most importantly you have desire and enthusiasm." Pause.

"Here's what's going to happen if you decide to accept this challenge. Whatever life you are living now-you have to forget. You will have to come and live with me here. On a daily basis I will train you to be a woman. How to walk. How to sit. How to talk. How to put on makeup. How to flirt. When I said we will go out I meant that. But it will almost surely be several times we go out. Just to see how well you took my instructions."

"But there are things we have to talk about." Another pause. "Most importantly your name." I must have looked confused. "If I am going to make you a woman you can not go by your birth name." I realized she was right.

"So--ummm-ok-how about Dee then?" I inquired.

"Good enough" she nodded.

"While you are here in your off time you will live as woman. Dressed as a woman. Act like a woman. BE a woman." A skeptical glance. "This isn't for everyone. You are not my prisoner. Any time -and I mean-anytime you are ready to go-GO."

I nodded. "Yes"

"You will have to get a job-because what's going to happen isn't cheap. And honestly it shouldn't come out of my pocket. This is something you want. And if you don't realize that you need to think hard and long about this path you are about to take."

I had accepted all the terms. Got a job at a toy manufacturing factory and started my training. Being a woman is hard. You walk differently. You talk differently, You act differently. You even think differently. Make up. The way you sit. Actions in public. I was extremely ill-at-ease-for the first couple of weeks. When I wasn't working I wore women's clothing at home. I had no problem with-but what made me uncomfortable was the number of people that seem to come and go all the time.

But I got past it. And one day Estella came to me. She laid out pink jeans, white panties and a strapless bra, a white halter top, white tennis shoes with pink laces. And something that was brand new-breast forms.

"I have a friend who works at a prosthetic department for a medical clinic. She experiments with everything. But her passion is breast forms for women you have had breast cancer. When you use these correctly you will give the illusion of having 38C breasts. Let's get started. You are going out today."

I put it on and we went shopping. I was nervous of course. But pleased when I realized that there were guys checking me out. I began to enjoy the attention. It was a great day.

Some days later Estella informed me we were having a BBQ in our backyard and that I was going to have to be on my best behavior. I agreed

The day of the BBQ Estella laid out some clothes for me. Matching pink bra and panty set, jean shorts, white halter top, a pair of shoes that looked like sandals except they had a 2-inch cork heel. And a new set of breast forms that looked "fuller" than the one I had used for shopping.

There were dozens of people at this BBQ. Mostly guys and mostly unknown. That being said that didn't stop most of the guys slapping my ass, groping my ass, and otherwise trying to work their fingers into my shorts and up my ass. The entire afternoon was a history of me being molested-and I found that I loved it. Soon-almost everyone was gone and Estella pulled me aside.

"You did well Dee. I think it's time for you to go out with a real man-this is what I meant when I said when you are ready we will go out." I nodded my understanding.

Several days later Estella came to my room with a brown bag. My interest was intrigued. And when she dumped the bag on my bed it revealed two very large very realistic dildos.

"You have a date with Carl on Saturday," she looked at me, "No idea how far you want to take this but I brought these just in case you wanted to practice."

Saturday rolled around. My date with Carl was going to be at a country themed bar. Estella and I had spent most of Friday searching for just the right outfit. When we were completely done I had matching robin egg thong and bra, white mid-thigh skirt, a decidedly country shirt mostly light blue, white cowboy hat, and white open toe strappy heels. As hard as we looked we could not find a pair of women's cowboy boots that fit me-so we had to settle for the heels.

Late Saturday I painted my nails (fingers and toes) to match my red cum-fuck-me lipstick. I put the outfit on. And as I waited for Carl I looked in the full length mirror and I was pleasantly surprised how sexy and erotic I looked. This was really happening.

Carl showed almost exactly when he said he would. Taller than I thought, dark hair-touch of gray, kind eyes, easy smile. I felt this was going to be a success of a night.

The line for the bar we were going in was long and moved slowly. As we waited and trudged forward I thought about this night. I knew I was anxious. This was going to be my first true night out as a woman. And I hoped it went well. Carl small-talked for awhile. But at some point I realized his hand was on my ass and he was cupping and squeezing and fondling my ass. I was complimented by this action but I also knew he knew what I was. And he might just be trying to put me at ease.

We finally ended up inside and found a table not too far from the dance floor. We drank a little, danced a lot. At some point we were sitting down, drinking maybe our third drink. And without much warning I found his hand inside my inner thigh caressing me. He was erotically close to my 5-inch penis. And I could feel myself stirring. He leaned in close-his lips less than an inch from my ear.

"How much do you want to be Dee?" he asked . Plain enough. But the implication was there.

"More than you can imagine," I whispered.

With no more invitation than that he cupped my chin, pulled me close, and started kissing me. I was a little startled at first. But responded almost immediately. I opened my mouth and accepted his tongue, his kiss, his love. I felt his tongue roaming around in my

mouth. Our lips were touching, he was sucking on my tongue, and his hand had found it's way into my panties. He was thumbing my little cock, groping my crotch. I spread my legs as far apart as I could get them to allow full access. I was grinding my hips into his hand and sucking on his tongue. At the rate I was going I would be hopping up on the table to get fucked. Fortunately for me it didn't come to that

"Let's go to my place," he whispered. I didn't have to be asked twice.

Once at his place he got us some drinks. We sat on his couch. Close enough that I was almost in his lap. Carl was caressing my neck, my cheek, my inner thigh. His hands were everywhere. At some point his hand got tighter on the back of my head and I realized he was guiding my head into his groin. At this point I realized I was almost past the point of no return. And I made a decision.

My hands struggled with his belt. His buttons. His zipper. His jeans. Luckily for me Carl was very helpful. And finally his cock popped free from his jeans and underwear. It wasn't the size of the dildos that Estella had me practice on. But it was sturdy.

With no pleading from Carl whatsoever I dropped my mouth on to his rigid meat. I felt the head press into the back my throat. I could taste the stiff flesh as it slid along my tongue. It felt good. It felt natural for a hard cock to be pumping my mouth. It was at this point in my life that I realized I loved the feel of a big hard dick in my mouth. Carl grabbed me by the sides of my head and started fucking my mouth. His hard thick cock was sliding in and out of my hot wet eager mouth. The pulsing veins stretching my mouth, the head hitting the back of my throat, the sweet taste of pre-cum coating my tongue. My heavy breathing and his soft moaning were the only sounds in his apartment as he fucked my mouth-making me aware of who I am. I realized that at some point his moaning was louder and his rhythm was increasing. I knew he was close. Almost as soon as I thought that thought I felt a flood of sperm in my mouth. As I was swallowing as fast I could I realized that I loved the taste of cum. I tried to slow the cum flood so that I could taste and savor the offering I was given. But Carl was determined to drown me in his jizz.

Twenty minutes later-the taste of his cum still in my mouth-we were in the bedroom. As I prepared to strip down he stopped me. Turns out he wanted to strip me himself. He unbuttoned the side button of my skirt and let it drop. I stepped out of it. He hooked his fingers into my panties and stripped them off. I now stood before him-my 5 inch penis hard as a rock. Very gently he placed his hand between my legs and caressed my penis. I was unable to NOT moan. With one quick movement he scooped me up and placed me on the bed. He rolled me over so that I was on my belly and my ass was in the air.

"Ready?" he asked quietly. I was more than ready. I felt the bulbous head of his rigid cock at my anus. I prepared myself for what was to come. And then I felt it.

The head had forced it's way into my anus with little more than a gasp from me. I felt the firm but continual advance of his hard thick cock up my ass. And I finally felt his balls on my ass.

Then he started to withdraw and knew the fucking was just seconds from happening. And I was right. He pulled me up to my knees by intertwining his fingers with mine and pulling me up. And for the next 20 minutes I felt his cock slamming my ass. I was grunting, and groaning, and moaning. At some point I heard him say, "Jeez Dee what a slut you are". I felt this was fair and said nothing in return-mostly because the continual assault on my ass made it hard to breathe let alone talk.

Finally he took one final plunge deep up my ass and yelled, "Goddamn Dee darling," and emptied his hot love offering up my ass. Several minutes later he pulled his still half hard cock out of my ass. dripping white seed everywhere. But mostly at my cock opening and down my quivering thighs.

He pulled my head around and with his cock just seconds out of my mouth shoved it in my mouth. I cleaned the cooling cum from his cock. I smelled my ass and I could taste my ass. But still I was dreamy and sated.

I would leave Estella's within 6 months and later down the road I would realize this was where Dee Darling was born.

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3 Comments
AnonymousAnonymous10 months ago

Thanks for the afternoon hard-on.

AnonymousAnonymousover 6 years ago
Hot

Just like my first time dressing for a man .. I had taken time to make myself as feminine as possible .. he was impressed at my look - as was I - we spent a lovely evening in his house , culminating in his cock emptying itself in my ‘mancunt’

I moaned and wailed like a cheap whore in a porn movie !!

AnonymousAnonymousover 6 years ago
comment

auadruple double 5 star omg !!!!!!!

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