tagTranssexuals & CrossdressersPool Boy Gets Dressed Up Ch. 01

Pool Boy Gets Dressed Up Ch. 01


I loved my job as a part-time pool maintenance man, or pool boy as everyone loves to call it. I just finished high school and enrolled in night classes at the local junior college, that don't start until September. Having night classes will allow me to work my part time job during the day. I loved going from beautiful house to beautiful house, cleaning and testing pools, wearing only shorts, a tank top, and flip flops as my uniform. Florida is so nice in the early summer. Most of my customers are at work which leaves me time to clean the pools and sometimes take a nice dip to cool off. I am really shy so I prefer to be by myself all day and not have to interact with people, while I am still going through the awkward teens.

My name is Brandon; I am 5 foot 6, 120 pounds, dark brown hair which I keep real short so that when I swim I just have to shake the water off without worrying about weird hair. Thanks to my Italian genes, I have green eyes and a smooth almost hairless body. I am really self-conscious about my body. I just turned 18 and I don't think I have finished puberty. The hair on my legs only grows on my front shins. I only have a couple hairs in my arm pits and not much more grows around my cock. I have small budding breasts with large puffy areolas. My nipples are large and stick out over 1/4 inch. I shave my cock, balls, legs, and even my arm pit hair, just because I prefer the more even look over that intermittent sparse hair growth I have going. My biggest embarrassment is my cock; it is still the size of a little boy's. My cock is about 4 and a half inches hard and really skinny, a real pencil dick. I am hoping this will all develop one day soon.

One particular day it was hotter than normal and the pool I was working on was enclosed in an atrium room off the home's living room. There were huge picture windows and sliding doors that allowed anyone in the home to see the beautiful patio, bar, spa, pool, and waterfall. It is my job to make sure that all the rocks and tiles are kept algae free and the pool balances are perfect so that the water is crystal clear. I was only wearing a white small speedo and tank top, since nobody is ever home during the day.

I only met the owners once when I had to come on a Saturday. The wife is a gorgeous blonde woman that is at least 6 foot tall, nice set of boobs, slender build, and legs that go on forever. Her husband was about 6 foot 4 inches and looked like a Greek God, shiny black hair, steel blue eyes, and thick dark black hair on his olive tone arms and legs. They introduced themselves as Debra and Don, and they both looked to be in their early 50's, very wealthy, and in very good shape for their age.

I had introduced myself and told them that I usually come to their home on Fridays but I had finals and my school schedule changed for this week only. They said that they were pleased with my work, and even though I was out of school they hoped that I would continue on as their maintenance person. Then Don made a point to let me know that if I had to leave the company for any reason that he was to see him first and that he would at least offer to keep me on as a side job and would work around any schedule I may have.

Debra showed me around the pool area and bar, she told me to always help myself to anything they had in the bar as long as I didn't drink and drive. As she said that last part she put her arm around my shoulder and pulled me in for a quick hug pressing my face to the side of her exposed breast, then laughed at how red I had gotten. I thanked them and went about my business cleaning the pool while they drank and talked to each other.

That was in May at the end of my semester and now here it was mid-July and I had never run into either Debra or Don, so I felt safe wearing only my speedos. I was bent over the waterfall rocks, scrubbing them down, when I heard the sliding glass door open up. I looked up to see Debra as she was walking out of the house. She was wearing a hot bright orange bikini, that was really just small patches covering her nipples, a little triangle covering her pussy lips, and held up by a little string around her waist and ran down the crack of her hard as rocks ass cheeks. She was caring a towel and a book.

'Oh shit, I'm only wearing my speedos,' I thought to myself as I jumped up, grabbed my shorts, and quickly bent over to put them on.

Debra called out to me from across the pool "Hi Brandon, how are you doing sweetie?"

I stumbled something stupid, "Um, fine Mrs, ur um Deb..Debra ma'am."

Debra shot me a quick look before she started to scold me, "Brandon don't you ever call me Ma'am, I'm not that old. My name is Debra or Miss Debra if you wish, and for gosh sakes stop fumbling with those shorts, it's hot and you look just fine in your cute little speedo there, now put those shorts back down and go about doing your business."

Though it came out kind of rough and loud, I'm sure she didn't mean it like that. I dropped my shorts right down as I was told and quickly began to apologize for calling her ma'am, "Yes ma'am, I mean Debra, ur..uh.. Miss Debra."

'Stupid, stupid, stupid' I thought to myself, this is why I don't have girlfriends I get all tongue tied and stupid around beautiful women, and I could feel myself turn ten shades of red.

Debra put her towel and book down on one of the lounge chairs and then walked over to the bar. "Hey, Brandon do you want something cool to drink?" Debra called out to me.

"Uh ya sure that would be great thank you Ma...um Deb..Miss Debra." Crap, idiot strikes again.

Debra laughed at me "Hey, Brandon how about I just get you drink and you walk over to that chair and sit down, that way you don't have to stumble on your words every time you open your pretty little mouth?"

Rather than make a bigger ass of myself, I put the scrub brush down and walked over to the lounge chair and sat down. Debra walked over to me and handed me a drink. As I took the drink from her hand it was clear that I was nervous as the drink was shaking in my hand making the ice jingle in the glass.

"Calm down there little guy nobody is going to hurt you." To add insult to injury she said that and patted me on the head like a little kid.

I was eye level, almost, with her crotch and I could see the bright orange patch covering her clit which was not covering it at all. Her pussy lips were sticking out from the sides of the material, which was attempting to be a bathing suit. I almost lost it then and there; thank god she pulled away and sat down with her drink.

Debra attempted to get me to open up, "So Brandon what do you do when you're not in school or cleaning pools?"

I took a quick drink thinking it was just a cola but it had a lot of rum in it and I choked. Debra laughed at me, and in a patronizing tone said, "You ok there honey? Did I make it too strong for you?"

"No, um, I just wasn't expecting it to have booze in it. I'm good, thank you." I tried to pull off coolness by taking a large drink of the rum and coke, but already having choked my voice sounded like a little boy trying to act like a grown-up.

Debra reiterated her question "Ok there stud. So what do you do when you're not here in my backyard running around in a little skimpy bikini bottom?" This made me blush again so I took a long swig of my drink, and choked a little again.

It was getting really hot now and I was getting light headed and loosening up a bit as I answered her question, "Nothing really, just play video games and surf the web mostly."

Debra reached over and grabbed my thigh, "What? No girlfriend to keep you busy Brandon? I'm shocked, good looking boy like you I would think girls would be all over you."

She ran her hand down my thigh to my knee, "My, your leg is as smooth as mine." At that last comment I jerked my leg a bit and her hand came off my knee, I was again embarrassed.

She shot me a firm look again, "Oh don't be like that Brandon, it's no big deal that you shave. In fact, I find it a nice change from Don's big manly hairy legs."

I confessed that I shaved the little hair I did have because I thought it looked stupid growing in sparse patches on my legs, after the words left my mouth I wanted to crawl in a hole and die.

Instead Debra just went with it like it was no big deal, "That's very sensible, and I suppose you shave your cock and balls so you can wear that little bikini bottom? That's why I shave my pussy too, seems we have some things in common don't we honey?"

I agreed with her as I took another gulp of my drink, "Yes Miss Debra I guess we do, thank you for not thinking I'm weird for shaving. I've never told anybody that before."

Debra smiled at me and placed her hand back on my thigh, "Oh sweetie you can tell Miss Debra anything you want, this is totally safe zone for you. Just relax. So why don't you date girls, afraid they will find out your little secret?" Debra began to lightly caress my leg.

I nervously downed the rest of my drink. Debra was quick to get up and make me another. As she returned with our freshened drinks, instead of returning to her lounge chair she sat next to me, forcing me to move over a bit to let her sit. Before I could pull my knees up toward my chest, and hide my hardening cock, Debra had already put her left hand across my legs and laid her upper body across me pinning my legs down.

I took another long swig of the rum and coke to settle my nerves. I tried a quick tug of my shirt to try and hide my crotch; no luck the shirt was too damn short. Debra lay across my legs facing me, her right hand softly stroked my thigh, "So you say you surf the web, I bet you surf a lot of porn don't you Brandon? Remember anything you say here stays here."

Debra was talking in the softest and most sultry voice I have ever heard. Her voice had me mesmerized. My mouth just opened up and I could hear myself talking and I couldn't stop myself, "I surf porn, I like watching videos of people having sex while I jackoff."

""People" what an interesting word to use. Do you like watching women and men fuck each other, or maybe two women getting it on? Is that what does it for you, lesbian porn?" Debra was prodding me and I must have had a blank and shocked expression on my face.

"No? Then bi porn, a woman getting fucked in her pussy while her man takes it up his ass?" My cock twitched at that and I could see a smile cross her face.

Debra continued to torment me, "Maybe a little curious and you peaked at gay porn, two guys fucking each other and sucking on each other's cocks, have you looked at gay porn Brandon?" Again, my cock twitched and I could feel a drop of cum seep out through my suit.

"Oh everyone is curious Brandon don't feel bad. Boy's like to look at men's cocks to see what they might grow up to be like. I'm sure you've checked out the boys in the shower after gym class haven't you? Your dad while he was changing maybe?" Debra just kept looking into my eyes and leaned her body closer to me.

Her body shifted and I could feel her waist pressing up against my little cock and balls. Then she took her hand and ran a finger down my face, it felt so good. I heard her voice again "Have you ever watched Tranny porn Brandy baby? Do you like seeing boys dressed in silky nylons and a pretty lacy bra pressing against their poky little nipples? Feel a real man put his big hairy body on top of them as he feeds his big man cock in their waiting mouth?"

I lost it, I threw my head back, my legs started to shake, and I squeezed my cock as hard as I could to hold back the cum. When my little orgasm stopped, I released the tension on my cock. I could feel a big glob of cum seep out of my cock head. Looking down at my lap I could see that my cock was pressed tight against my speedo and my cum came out through the nylon forming a big glob right there on my cock head. I was so embarrassed; I needed a hole to crawl into.

I looked up at Debra and she was staring at me with a big wicked smile on her face. Debra leaned back away from me and followed my eyes down to my lap. I watched as her hand came down to my cock and her finger scooped up the blob of cum off my speedos. Her hand came up to my face as I heard her say in that sultry voice, "Good little sluts always clean their messes up Brandy sweetie, now open your mouth baby."

Without even thinking, or having any sense of control, my mouth opened a bit, her finger entered my mouth, and then she fed me my cum. "Now be a good dear and clean Miss Debra's finger off." I just closed my mouth around her finger and closed my eyes. My tongue took on a mind of its own as I slowly searched out the cum off her finger.

"That's it baby suck on it, feel that nice thick juice in your mouth. Play with it, get to know its feel and taste." Her finger slowly pulled out of my mouth and I was left with my cum on my tongue. I moved it around feeling the thick slippery feeling, it was heavenly.

I never tasted cum before, let alone my own. As often as I jack off I never thought to try it. It tasted really good. Then I realized that I was eating my own cum in front of a woman and she all but made me confess my deepest desires. I turned my head away from her and I tried to twist out from under her but she had me pinned down, her hand was stroking my leg and moving up to my speedos. My cock was hard as a rock and straining to pop out the top of my speedos. I was dripping so much that the wet spot was growing bigger and bigger.

I felt a firm grip take hold of my shoulder, "BRANDON STOP" Debra yelled at me.

I froze at the sound of her voice. "Brandon, stop it now, relax. There is nothing to be ashamed or embarrassed about. I am sorry I brought up the subject; I didn't mean to make you feel so bad. Sometimes I see a sexy young man and I just have to know what he desires. When I saw that you shaved your legs I had a hunch you might want those legs covered in silky nylons. By the little orgasm you had, I think I was right wasn't I sweetie?"

My eyes went wide open and my voice was gone. I could feel the tears well up in my eyes and my chest started to feel heavy as I fought back the emotion. Debra looked at me, "It's perfectly fine with me baby, I said this was your safe haven. I would never tell another sole what goes on here. I think it is extremely sexy to see a man in girly things. In fact if you want to, I would be more than happy to let you dress up here as you want, it will be our little secret?"

I didn't know what to think. Sure I surfed porn on the web, who doesn't? Like most people I "accidentally" would come across bi porn and it made me wonder what it would be like to be with a man and a woman. I was still a virgin so I have nothing to compare anything to, except my right hand. I didn't know what I wanted, men or women. I was confused. Gay porn was cool but it always seemed that the guys just jump on each other and go for it, no playing or seduction in those movies.

The tranny porn was hot. I loved watching the story lines where the guy doesn't know he is making out with a guy until he finally drops his panties. I love to watch the tranny films where the boys have nice real tits and not just stuffed bras. But now I am sitting in front of an almost naked goddess and she wants me to play dress up with her. I was so confused, and what if Don found out? I would lose my job and probably get the shit kicked out of me.

I shyly told Debra, "Thanks, but I couldn't. I have never done anything like that. I would feel funny undressing in front of a beautiful woman let alone wear girls clothes. What about your husband, what if he came home and caught me? He scares me."

Debra looked at me and smiled, "Oh Don is out of town more often than not, don't worry about him. I just want to help you find what makes you happy, just try a few things and we will find your true sexual calling, trust me. It will be like having my own little play friend. Besides Don is gone for a week, it's Friday, and I have no plans all weekend."

With that she leaned over and gave me a quick peck on the lips, and then she put her hand on my still hard cock and said, "Looks like someone wants to play." as she rubbed my cock.

Debra sat up, hooked her fingers on either side of my speedos, and pulled them down and off my legs. My cock slapped back against my tshirt as my hands quickly tried to cover myself. Debra easily slapped away my hands before I could cover up, "Come on baby now is not the time to be shy, let Miss Debra see what we have to work with."

Debra grabbed my tshirt and pulled it up and over my head with such force that I couldn't even stop my arms as they went straight up in the air with my shirt. Debra threw my shirt off to the side and I crossed my arms to cover my budding nipples.

Debra would have none of that, "Hands down Mr." Debra commanded, and my arms went straight to my side. I felt my face turning bright red as I tried to turn my head in shame.

Debra grabbed my chin and turned my face back to her so we could look into each other's eyes, "Stop being so embarrassed, you have a lovely body."

Debra looked me over, "OH MY, those budding titties are lovely." as she said that her hand left my chin and softly touched my left nipple. I let out a soft moan of pleasure. Nobody has ever touched my nipples before. It was like electric shocks went through my body and right down to my balls. My cock flinched and my nipples started to get hard and poke out.

"You like that don't you baby, see it's all about feeling good. You have the biggest areolas I have seen on a man, and bigger than a few women I know, simply lovely."

She was staring at my nipples, massaging them, rubbing them, lightly pinching, and pulling the nipples making them really hard. Almost to herself she said, "Oh yes this is going to be the best transformation ever." I didn't know what she meant and I really didn't care, I was just enjoying the feeling of someone touching me.

Just as fast as she pulled my speedo off, she crawled in between my legs. I felt her hair fall on my stomach as she put her head in my lap and I felt a warm wet sensation around my cock. It was so hot and her tongue was all over my cock. I was so small she actually took my entire cock and balls into her mouth. Her tongue darted out behind my balls, then back in her mouth swirling her tongue around my balls. I couldn't hold back, "Oh god no, I'm cumming, stop please stop I can't hold it back." with that I felt my cock tighten up and spurt three or four powerful bursts of cum into Debra's mouth.

Debra pulled up a little and sucked out some more cum. My head was spinning, my first blow job. Debra lifted her head off my deflating cock, reached her hand behind my head, and pulled me in for a kiss. Without thinking I just let her guide me to her lips. Her tongue forced itself into my mouth. The grip on the back of my head became tighter as she held our kiss. She parted her lips and my mouth was filled with her tongue. I felt a warm liquid flood into my mouth. We continued to let our tongues dance until she pulled off my mouth. She held me so close that our noses stayed touching, "All good sluts clean up after themselves, now swallow your load honey."

The first time she fed me just little bit of cum I didn't think it was bad at all. This time I have a mouth full of my own cum, fresh my cock. I was too turned on not to have swallowed. It felt so good going down, and I actually liked the taste. I looked back at Debra with a proud smile on my face.

Debra stood up and held out her hand for me to take. I took her hand and she pulled me up next to her. She towered over me like a beautiful amazon woman, at least in my mind, "Come on, let's take a swim in the pool." with that she pulled me towards the pool.

When we got to the edge of the pool she pushed me in the water. When I came up laughing, she was untying her strings on her bikini. She released her breast first, tossing her top onto the chair. Her breast were the most beautiful I have ever seen. Her 36b's were held nice and high and firm on her chest. They each had large pink areolas with large protruding nipples, and her right one was pierced with a gold ring.

Report Story

bytonyl65© 21 comments/ 221004 views/ 162 favorites

Share the love

Report a Bug

3 Pages:123

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: