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Full Version: From a boy to a gurl
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The beginning:
Saturday a week before payday at the Pendleton Marine Base in Southern California.  Short of money I had thrown my flippers, mask, snorkel and prybar into a travel bag and thumbed a ride down to La Jolla to see if I could catch a few abalone to sell at the local restaurant.  Diving in the kelp beds just off the rocks had been productive and I had sold five nice shells.  It was illegal at the time to sell wild caught game, but the restaurant owner was willing to buy them, so I now had a few bucks in my pocket.  I had sold him fish before, but abalone were what he ask for, that’s what I pried off the rocks. 

Walked out on the 101 and stuck my thumb out looking for a ride back up to the base where I would be able to clean up.  At 19 years old, just back from a year in Korea. Even though I was wearing Levi’s, sandals and a T-shirt, it was obvious where I belonged with my short hair and clean cut straight back stance.  This was during the time when cruddy clothing with dirty facial hair was fashionable, so I got a ride quick.
Where you going, Oceanside he asks? 
I replied San Clemente, and he smiled. 
The next thing he said was I’ll give you twenty bucks if you let me suck your cock.
I looked closer at him, a little older maybe forty something, short and rather stocky.  What the hell twenty bucks is a lot of money in 54, so I said OK.  Still in La Jolla, I expecting him to find a place to pull over by the beach and do his thing, he instead pulled into a motel parking lot.  He got out and went to one of the unit’s doors, opened it saying come on in.  He already had the room, so maybe he owned the place, but then maybe a trap.  Leery because back then homosexual acts were illegal, could get you locked up, plus a dishonorable discharge, but you know, twenty bucks was almost half a month’s Marine pay. 

I walked in behind him as he pulled a twenty out of his wallet and laid it on the table.  I set my travel bag on top of it.    He started undressing so I figured he wanted me to do the same.  I ask if I could take a quick shower as I was still all salty from the ocean water.  He said he liked a little salt on his meat.  I decided I liked this guy.  Naked he was a bear, very hairy and powerful looking for a short guy.  I flopped on the bed spread my knees wide, expecting him to get between my legs.  He got on his hands and knees, head over my crotch, put his hands under my ass and rolled back into a sitting position, pulling my crotch over to his lap with my legs wrapped around his waist. He lifted my ass until my cock was in his face as he bent over.  My half hard cock was sucked into his mouth in that manner, and he did suck hard on the head working the underside with his tongue.  In the military you don’t find a lot of time to get off, so it had been a while.

Being uncircumcised my dick head was very sensitive to his touch with the head out of its sheath, so within a few minutes he got my load.  It was very heavy and he swallowed much of it down with only a bit dribbling down on my balls.  It was only then that I realized he was rubbing my ass crack with the head of his dick while he sucked pulling me back and forth.  He looked at me with a question in his eyes.
Was that it he asks? 
I said twenty more and I’ll hang around longer.
Without an answer he went back down on my dick which was still hard.  I had been laying on my back with his folded legs up under my ass jutting my cock up in his face. 
For twenty more I get to play more with you?
Sure, whatever.
   
He told me to sit up, so I did with my legs now bent into kneeling position and still wrapped around his waist.  At nineteen years old I was lean and lithe from running around the base playing war and exercising daily.  A tad over six feet, a hundred ninety pounds, with plenty of muscle under a thin layer of fatty skin.  But I had been short changed in the testosterone department, for I had no body hair to speak of and a fat layer of soft skin like a girl.  It also gave me tits, very small ones like a little girl just going into puberty and not really noticeable if it wasn’t for my nipples.  My nipples were on a cone shaped areola that protruded a quarter inch or more away from my chest. On base, guys in the shower would tease me about them.  Sitting on his lap now with his arms around my waist, he started licking and sucking my nipples.  It felt good, as did the hair on his body pressed against my hairless belly skin.  He had started pulling my waist closer to him and I could feel his cock rubbing in my ass crack.  Wanting to earn my money, and actually enjoying myself, I started clenching my ass on his dick after he pulled me close. This went on silently for a long period of time and as it did, he produced so much pre-cum my ass crack was now really slippery.  Every time he pulled me to him his dick was pressing hard on my little pink virgin ass hole.  While I had never been fucked before, I was curious now.  I relaxed my body as he pulled and his dick head went in just a bit more with each pull. That was when I pulled with my legs and slid my ass forward pressing down on his cock a fraction.  I could feel his dick head putting pressure in my asshole as he sucked on my nipples.  My nipples were sending waves of pleasure down my front so it felt good.  I had almost taken over the movement thing and was working trying to get more of his cock up in me.  A little lube would have done it. 

He provided that lube in the form of a heavy load of cum up my partially open asshole.  By pressing down as he continued to cum, I felt his dick head pop through and in.  While it was only six inches or so, it was in and it felt really good.  He fell back on the bed panting breathing hard. Now I was sitting on top of him his still stiff dick up my ass as far as it could go.  I was loving that feeling and tried to keep it going.  I moved my ass working his cock in and out.  It must have felt very good as he made little whimpering sounds of pleasure.  I was trying to keep him excited, however eventually he went soft and his dick fell out.  Cum ran out of my ass leaving a trail all over his chest as I moved my cock close to his face in case he felt like a little more sucking.  He had a few licks, but was wiped out so I went in the shower.  Did a quick clean up.  He was still in bed up on one elbow when I came out.  He watched me dress with satisfaction on his face.  I had taken the twenty out from under my travel bag and put it in my pocket, when he said hand me my pants there will you?  I did, he got out his wallet, pulled out a twenty and a ten.  As he handing them to me, he said here, you earned it.  I was pretty pleased with what I had done for him, and for me.

2nd lesson:
Back out on the highway, I stuck out my thumb again.  A few minutes later a little green MG pulled over to stop.  He asks me where was I going, I told him San Clemente as I got in.  The wet bathing suit and swim gear had seeped through my travel bag making it wet, so I set it on the floor in front of me under my feet.  He said you been swimming.  I said yea, and the conversation went on with me telling him how it was the week before payday on the base.  I had no money and was diving for abalone to make a few bucks.  General chit chat about snorkeling went on for a few miles.  When we were on the open road, after shifting gears he would put his hand on my leg.  As I didn’t object next shift it went a lot higher, so it was not accidental.  Not too many shifts later, it was going straight to my crotch, and me wearing tight Levi’s meant he had a handful of balls to hold.  I didn’t object and tried rearranging myself as the Levi’s were tight and my dick wanted out. I unbuttoned the waist button to let it pop out the top of my waist band under my T shirt.  I was enjoying it and tempted to pull my pants down so he could play while driving but to many small towns with stopping for red lights in a small low car, I decided just letting him rub my dick head was enough. 

After Oceanside just before San Clemente he came out with it and said, want blow job?  I did but now wise to the game, I told him twenty bucks would really turn me on.  It was now dark with a full moon, he found a dirt road to the beach and turned into it.  He pulled a blanket from the back as we exited the car.  Checking him out, he was a tall, strong bodied mature man who could have been a military person himself.  Wearing shorts and an open shirt he was quite handsome in the moonlight.  I took my clothes off as he dropped what he was wearing on the blanket.  We sat down on the blanket. He was fascinated with my body in the moonlight, running his hand over it as he played with my dick and explored.  I liked the part where he would do little rings around my asshole with his spit and finger. 

My nipples now almost back to normal after the stretching workout they had earlier, were hard from the cool night air.  He kept rubbing and pinching them. I was holding his cock in my hand playing with it.  I had never held a man’s cock before.  It was firm but not solid hard like mine.  I was sitting watching him, when he laid down on the blanket.  Motioning me to also lay down, I did and he moved to put my cock in his mouth.  His hips were turned so his cock was facing me as I played with it, slow stroking.  His cock head was now sticking out at my face, so I put it in my mouth.  The taste was not what I expected, it was just skin like sucking my thumb.  He was sucking my dick with a steady motion that felt really good, so I tried doing the same thing to him.  He said you’ve never done that before have you?  I replied nope, first time.  My dick was now rock hard, almost eight inches with a seven-and-a-half-inch circumference, and he was rubbing it with lube.  He smeared some on his ass hole and rolled over on his belly.  His ass all white in the moon light looked hot when he said fuck me.  I got on top of him, and started working my dick in it.  Getting past the tight spot I found the best feeling my cock had ever felt.  A warm tightness that gripped the shaft when I pulled back and heated the head as I went in.  I had fucked many women, it was a thing Marines do in foreign countries, but I had never had a pussy that felt this good.  I started pumping hard looking for the cum release, but he twisted a bit and said slow down there’ tiger.  Slow and easy is best, he had raised his ass in the air. 

He pulled out from under me and rolled over on his back now.  Raised his legs and feet in the air, I was back in his asshole again.  Slow fucking him, I could see the pleasure on his face in the pale light of the moon.  It made me feel good that I was providing it.  He was holding his own cock, pulling on it as I slammed into his ass hard with each stroke.  After a period of time doing that, he moaned and shot his load on his chest.  He reached up and started pulling and pinching my nipples hard, that was enough to make me cum like I never had before.  Actually, that first cum up his ass was the best dick feeling of any cum that came before or after. 
Afterwards, I went in the surf and washed off then, as we dressed, he said he had a place local if I wanted to spend the night in town.  I thanked him, explaining I had the duty for the weekend so had to get back, maybe some other time while putting his twenty in my pocket.  He dropped me off at the base entrance, and as I got out of his car, he gave me his local business card after writing a phone number on the back.  He said need a few bucks again, give me a call.  I put it in my pocket.  Back on base, walking back to my area, I was pretty pleased.  Diving had earned me eight bucks, but I had seventy from enjoying myself learning new tricks.  I took his card out of my pocket and put it in a safe place in my wallet. 
1027

I had duty that weekend.  It was a payday weekend so all the friends went to Tijuana and had a blast.  I couldn’t go so when they staggered back ragging on me about what I had missed, I laughed at them.  The next Friday they were getting primed to again go and get wasted.  I begged off.  After chow I went over to the PX and made a phone call to the number on the back of his card.  Hello, this is Dan, you told me a week ago you might have a job for me.  He said he remembered me and said he was just closing the office.  He would meet me at the donut shop.  I jumped on the 5:30 buss to town and walked over to the donut shop.  I didn’t see him so sat down.  Before I could order anything this super sharp gorgeously dressed guy, picked up his coffee, moved over and sat next to me saying hello Dan.  What a change clothing makes on a person.  I hadn’t recognized him. His stance was still domineering and powerful, but he now looked the part.  We had a brief conversation over coffee and left.  He was driving a big expensive car this time.  Short ride to his place overlooking the ocean was uneventful as we talked to establish a more personal connection.  Inside he showed me the fridge, telling me to help myself and left. 

I pulled out a beer and walked over to the patio doors looking out on the pool.  Before long he came out naked with a towel over his shoulder.  He dropped the towel on a pool chair and dove into the water.  Without a word, I knew what was expected, so I ditched my clothes and joined him in the water.  He laughed and told me to get out wet and walk around the pool apron a few times.  The sun was low and wet I looked great when I checked my reflection out in the glass patio doors.  After strutting around a bit, he told me to look up at a house on the hill overlooking his place.  Seems the guy who lived up there was a peeper with a telescope, and Dave wanted to show off his new toy, me.  I laughed at that.  I got back in the water with him and we swam a few laps, before he wrapped his arms around me pulled me close kissing me on the mouth.  I had never kissed a man before but it seemed natural to relax and let him control everything.  His hands were on my body rubbing all over.  I was being seduced and I loved it.  We spent a long time messing with each  other’s body in the water. I seemed to be floated on my back a lot as Dave would give a suck now and then on my nineteen year old stiff flagpole cock.  Eventually we moved to a chaise lounge chair where the peeper could watch. 

Dave had laid down on his back, with his crotch facing the peeper.  He had a stiff dick and I knew what to do.  Kneeling and leaning over from the side to not block peepers view, I wrapped my lips around the head, sucking on it while he gave me instructions.  My first time to actually suck a cock.  I was becoming educated in the fine art of cock sucking by a real Southern California pro.  Quickly gaining control of the gag reflex I was enjoying myself and he could tell.  He hunched his back shoving his hips in the air and groaned as he filled my mouth with cum.  So much cum it ran out of my mouth and down his balls, I licked the salty sweetness as I dribbled it on his asshole.  He slid out to the edge of the chaise lounge, moving around in front of him, my throbbing dick now found its target as he lifted his knees and gave me access to his pucker point.  Between his cum and my spit we were started to work it in, when I felt a tap on my shoulder and a hand offered some jelly. 

Seemed Dave’s partner had silently joined us. He had gotten naked and watched as I sucked Dave off.  I used the offered jelly going balls deep up Dave’s ass in a few thrust.  New guy was now standing close to the chair Dave was on, offering his cock to me, so without looking up I soon had a hard dick head poking me in the ear, so I sucked into my mouth.  We stayed like that for a bit, me sucking on him while I slow pumped on Dave.  He pulled out and moved down and with lube on his fingers started playing in my asshole. Dave was laying back knees in the air with his forefinger and thumb gripped tightly on my nipples, squeezing and twisting them to produce awesome pain sensations running from my nipples down to my groin.  The entire thing was blowing my mind coupled with my exhibitionist tendencies and thinking of the telescope guy on the hill watching.  All the physical sensations of Dave’s hot ass squeezing on my cock shaft, my balls sticking in his ass crack with every stroke were too much.  I did want to earn my hopeful pay with long play, but soon blew my nuts up Dave’s ass.  My entire body was quivering uncontrollably thrusting and slamming my nuts against Dave’s ass with every lunging thrust.

I crashed down on Dave’s chest and he wrapped his arms and legs around holding me tight.  After I gained control of my breathing, I realized I still had lubed fingers up my ass.  They were replaced with the cock head I had been sucking earlier. We must have looked odd to the telescope guy. My dick was still in Dave’s ass and I was being straddled and had a cock working its way up mine. I was being used like the whore I had turned into.  Remembering how good the guy in La Jolla felt, I wanted it deeper.  I pulled out of Dave, slid down until I was on my knees. Putting my face down on Dave’s semi hard dick, I sucked the head in and started mouthing it.  More lube was worked up my asshole, and the cock head started pushing again.  It went in a bit and I gasp.  Holy hell that hurt, but I was not about to stop.  He worked it in slow and it started to feel good. really good just enjoying the feeling up my ass.  Not as much as I had down in La Jolla, but it did still feel great.  Back to sucking on Dave’s cock head.  Ass dick sped up its thrusting and I stopped sucking.  Dave slid out from under me.  He knew what was to come.

Soon the dick in me was going nuts, fucking me like a rabbit.  I had fallen down on the chair and raised my ass pressing back on the dick in me. My asshole was getting hot from the friction.  My ass banger was really excited now and was racing to the finish line.  His smaller dick had warmed up from the rapid friction and soon exploded in my ass. Jab hold, jab hold, went on for a while as he pumped cum up my ass.  It felt great.  His hands were holding my hips, we stayed still, he just held on and soaked his dick in the cum he had shot up my ass, then after what seemed like a long time he pulled out panting, leaving me like Dave, both of us with cum dripping out our assholes.  Dave had a larger puddle from his ass than I did. I had a giggle.

The new teachers:

Dave broke the silence saying, this is Dan, he is working for me this weekend.” Dan say hello to Dee, he lives here. Dee was about five eight in height thin with a bare hairless body like my own, but with long hair and a smart little mustache. I noticed his cock was maybe 5 inches and rather thin in diameter. From the activity moments earlier, I thought he knows what to do with it. Dee was Dave’s longtime partner, they shared the house, but it was actually Dee’s property. Dave had sold it to him as a broker long ago. They hit it off and Dave helped him set up, both his house and his businesses. Dee had a few Beauty Salon’s along the coast and was getting well paid by rich women to mess with their hair, giving them special treatments, fawning over their appearance. His name was also David, but his salons were called Love by Da-Vyd. His customers called him Da Vid but Dave used Dee so I called him Dee also. I watched them together. Dave had made drinks and when he gave one to Dee, they shared a loving kiss. They were a couple but sex with me was OK in their relationship.
About that time Vinny showed up, dressed in white clothes he was a chef at the ritzy place up on the hill. He had a couple boxes of food from the kitchen when it closed. Fried chicken and cakes, so we ate with a few beers. Vinny was stocky, in his late thirties, nice looking guy. I wondered if I was expected to have sex with him now. Soon found out Vinny was married to Dee’s sister. He was just being friends, dropping off things from the restaurant. He had a few drinks with us then left to go home. The rest of the evening was spent socially drinking, me getting teased for being barely nineteen. A little food a lot of sex play, they were tired and went to bed. I wasn’t invited to join them. I was still naked under the pool robe I had been given when it chilled down. Dave said I was there for the weekend, so I went into the other open bedroom to sleep.

Sometime during the night, I felt a warm body next to me. Thinking it was one of the guys I put my arm around it and felt tit. Back to sleep thinking it was a weird dream. Morning came and I woke to find a young girl in bed with me. Not to look a gift horse in the mouth, I curled up with her. My dick was again hard. She woke up, turned over and ask who are you and what the hell are you doing in my bed. Not in a nice way, she was pissed. I tried to explain, but how do you explain to a naked girl you really want to make out with, what the circumstances were. She was very pretty and several years older than me. But she was pissed and I must have looked frightened. She said those bastards, referring to Dave and Dee. Our talk, well her yelling had woken the others and now they were watching and having a laugh. Looking at my morning stiffy, she said common, lets fuck. She teased me building my desire to peak, playing with my body sucking here and there making suck marks all over it. I went down and started eating her out. Now we were in something sexual I knew how to do. Growing up my neighbors had three girls and a horny mom who taught me. Working her clit over, she got off and I knew it was a good one. Then we fucked like crazy rabbits. Again, I was dumping my nuts heavy, she was pleased. She pushed me off her.

She got up to go to the john and told the laughing others, there I wore your boy toy out, you’re not getting anything out of him now you bastards. They had left her bedroom door open knowing I would go to bed in it and she would find a boy in her bed. She was Dee’s little sister and a bi-lesbian. Stomping around still naked she started making breakfast. Dave had dressed and left saying he had to open the office until noon on Saturdays. Lilly worked for her big brother in the beauty salons. I was hungry and ate some left-over chicken and cake, while I admired her body. She knew she was turning me on and was getting a kick out of teasing me again. Dee explained that I was his and Dave’s because Dave had purchased my services for the weekend. Lilly thought that was cool. I was the first rent a boy she had met. Dee said isn’t he cute, how old do you think he is. My face was still a kid’s face, I didn’t have to shave and my groin area had a few thin lightly colored pubic hairs, pretty much like a twelve-year old might have. She replied you better not let the cops know you have him, he’s maybe thirteen. Dee laughed telling her I was from the Marine base. Lilly replied he looks more like a girl with those little tits, he even turned me on. The abuse my nipples had been getting was showing in my chest now. I was actually getting a little cleavage. Lilly left for the shop leaving me alone with Dee.

A new boss:
Dee told me David said he was going to give me money for the weekend. What wouldn’t I do for money? I replied if your talking sexually, nothing. I enjoy sex with beautiful people, a little money makes everyone beautiful, and smiled back at him. He said I need to go for a ride, want to come along, we can leave a note for David telling him we will be back. We drove in Dee’s red XKE Jag up to a large house in the Laguna Hills area. Rang the bell and was escorted to a back office where a very large fat man looking like some kind of gangster from a movie was sitting behind his deask. Dee introduced me to him and mentioned that I might be willing to work his parties. Fat man looked me up and down, then said service guy, I don’t use service people. Dee told me get naked Dan. I dropped my pants and took off my white T-shirt. Fat man motioned me over and gave me a better once over with his hands. He told Dee, fucking beautiful. Fat guy said OK, I’ll use him. The deal was once a month fat guy had a party and had people who attended to the needs of his guest. The next party was two weeks away, I should be there at 2pm on Saturday. Handed me a bundle saying here’s your uniform. He told Dee to do something about the military haircut. I said OK, and we left after they joked around a bit more ignoring me completely.

Dee explained that I could make quite a bit of tip money at his party. To talk with Lilly his little sister, the girl I had met that morning. She also worked at his parties. When we returned to the house David was back from his office. Dee told him about setting me up in Laguna and he was pissed. David felt I was his find. I thought later Dee was a bit jealous of the way David was becoming attached to me. David took me out to lunch and left Dee in his den. There he explained that what I had signed up for was working at a party, where anything the customers wanted, I was to provide. He stressed the anything part again and said not many were beautiful people. Many were famous, and I was not allowed to admit I recognized them, was I sure I wanted to do that? I started having my doubts.

Learning the rules:
We returned to the house to join Dee and Lily over a beer and pizza with a skinny pizza boy. The rest of the day went like the evening before. Lily left, I fucked Dave, Dee was fucked by the pizza boy. The pizza boy was paid and had to leave. They sucked each other’s cocks then took turns fucking me while I played monkey in the middle with their cocks in my jaws. Dee dumped his nuts in my ass and David fucked in his cum to dump in me also then I cleaned Dee’s cum off his cock. That seemed to satisfy both of them. That night I was taken to town and dropped off with forty bucks. Dee said come back in two weeks, Lilly will take you to the party.

I spent the next two weeks doing the things Marines do. I didn’t go to town but after work in the showers I got ragged more about my tits which had grown more obvious from all the exercise they had gotten. Even Lilly had to mess with them, saying she felt evil fucking a child. My marine ID card said I was 21. While on duty I had stolen a blank, and created one showing I was 2 years older than I really was. With that in the states I could run around and do stupid shit in bars with the other guys. Time passed quickly, two weeks and I was back in San Clemente on Friday evening wearing shorts and a colored T with sandals.

I called Dave’s private number, but his secretary said he was out of town on business for a couple weeks, so I started walking up to their place, when I heard a car downshifting behind me. I turned and there was Lilly in the green MG. She had a friend in the passenger seat. Yelling hop in over the exhaust sound. I yelled back where, as I swung my leg over the door and tried not to sit on her friend while holding onto the windshield almost standing up. Her friend grabbed handfuls of my ass cheeks and pushed forward. This scenario lasted for a few minutes until we stopped in front of Dee’s place and I hopped out. Lilly introduced me to her best friend, who replied hi hard ass with a big grin.

Marian who preferred to be called Sunny for some reason, was a shorty, maybe 5-1 and perfectly proportioned, very pretty. She was three years older than Lilly and also worked the fat man’s parties. We were in the pool area when Lilly came out of the house with a plate of food, saying we should go raid the fridge. It was choice scallops or liver day on base so I had skipped mess coming straight to town. Sunny and I took her advice, we fed on more of Vinny’s leftovers while sitting at the pool table. Lilly explained to Sunny that I was going to work with them tomorrow. That opened the conversation on a more personal basis. They started laughing and teasing me, telling me stories of debauchery and humiliation from acts I would be required to perform. They scared me a bit, until they got to the part about how much money was in it for me.

My pay back then was a little over three grand a year before I enlisted. That part of California had people with a lot of money and who were willing to part with it for special entertainment. Fat man provided the special entertainment monthly. I was again warned not to let anyone know I recognized them and to never speak about what I would see or do. Not all the visitors were Hollywood types, some were big business and some were criminal, all of which needed anonymity.

Prepping for work:
Dee showed up and told Lilly to do something about my military haircut.  At that point it was a bit over the three-inch limit.  Lilly said let’s go, and we left to reopen Dee’s shop, there she put streaks in my sun-bleached hair some brighter and some darker. Then she added an agent that kept it from laying flat on my head.  Back at the house Dee complimented her on her talent while I didn’t understand what they were talking about. 

Sunny and I sat by the pool where I found out she had come out from Kentucky after winning a beauty contest and a promise of a job in the movies.  The movie job turned out to be working for the fat man, providing entertainment for his parties and a couple porn films.  She met Lilly in their shop and Lilly was complaining about money and her lack of it.  She introduced Lilly to fat man. She had started working his parties just a few months earlier.  Sunny clued me in as to what actually went on at his parties.  Sex was provided to anyone who wanted it anyway they wanted.  That was the basic game, but the people with invitations were all very wealthy and if they liked you, it was not uncommon for a large denomination bill to show up in your tip pocket.  Usually with a phone number wanting more attention privately.  The clothing provided consisted of an apron like dress with a front bib and tied with a large bow in the back.  Cotton with two side pockets and open but overlapping in the back.  The left side pocket was where the customers placed their tips in paper money.  Coins were considered disrespectful, so no one used those.  The pocket on the right held things like lube, condoms, rolled grass in a tin, and colored pills.  We carried drinks from the bartender and did anything requested by the patrons.  She then added you and she emphasized the you part, are going to be ask to do some weird shit, smile and make like you’re enjoying it.  We are really just classy whores and fat man is our pimp.

It was late, Lilly took Sunny by the hand and led her to their room leaving Dee and I alone by the pool to polish off the bourbon we had all been drinking from.  He was a little tipsy, we went to the bedroom he shared with Dave.  Now it was my first time to fuck him.  Unlike Dave, Dee had a really cold asshole, but he put something up his ass that made my cock head tingle.  That caused me to keep varying the depth and angle in his ass and numbed my regular dick sensations.  We fucked for a very long time, him loving the heat from my dick while I was trying to give him the most pleasurable fuck he ever had.  I found out later the shit he put on my dick would be great at staying power in a fuck and suck party. At nineteen years old staying up was no problem but I would cum quick.  Eventually we just quit from alcohol and lack of interest taking over.  What I was getting into the next day was on my mind.

Dee woke me the next morning getting dressed to go open the shop. Lilly and Sunny were still sleeping so I had a small fruit breakfast.  Lilly had warned me to not eat much and clean out well.  I used the shower and the small hose David had used on me the first day.  Remembering his advice, I didn’t use too much.  Already clean inside from Dee last night, just wanting to be sure no old cum smell was going to be present.  As I stepped out of the deck shower, Sunny brushed past going in and my dick responded slightly to the feel of her skin on my skin.  Yes, it was going to be a fun day I decided.

In Lilly’s room, her and Sunny were doing their makeup making themselves appear gorgeous. They looked like they were still kids which wasn’t far from the truth. I joined them, sitting by the mirror as they checked me out, made adjustments and did it again. My eyebrows; bleached from a life in the sun were colored and plucked to raise the outline more, a lighter tint was added to my skin that made me look much younger. My pointy little nipples had a tinting color applied to the areolas making them stand out. The same thing was applied to my lips, not so they looked like lipstick, just healthier and lush. Then with Sunny holding my shaft to keep it still and the uncircumcised skin pulled back, Lilly painted my dick head with the same color tint. She then rubbed the white part of my bottom where the sun couldn’t tan it with an artificial tan color. Not enough to cover the untanned, just enough to make it look as though I was doing something sneaky, like a kid would. They stepped back and admired their handiwork, commenting that I was gorgeous. Looking in the full-length mirror I saw what appeared to be a young kid, big for its age. Not a boy, not a girl, just someone you wanted to play with like a human doll. We were dressed in our uniforms as I called them, and ready to go. I was wearing the panties, while Lilly and Sunny were betting on how long they would stay on. The green MG had me sitting with Sunny on my lap, my dick was getting hard already.
On arrival we found everything already set up. Our tools were given out ready to use. Joints were rolled and placed in a thin metal container. Psychotics were in small bottles of two colors pink and green. Lube in a tube, all went in the side pocket on the right. Trays with glasses to be filled at the bar. The bartender was a big muscular man. I learned later he worked as an extra in the biblical movies popular at the time. He was also charged with keeping order during the party should anyone get out of hand. There was a clothing check girl who kept track of which boxes belonged to who for if/when someone shed a clothing article. She was a mature plump lady, who belonged to Fat man. I found her cute as she circulated among the high and drunken guest picking up pieces of clothing as they were shed, and placing them in the proper box. The pool area was open to the main room which was furnished with padded chairs small tables cushions on the floor. We worked arranging things and around 4:30 the guest started arriving. The entry way was being watched by the bartender. His trays were ready for the three of us to start circulating with.

The dining room off to the side opposite the pool had a long table already set food. Vinny had prepared a nice informal feed for those who wanted to eat. It consisted of fruit bowls, salads, and finger sandwiches that he had set up earlier. Some of the guest joined with others hugging and handling as if they were long lost best friends. I circulated the table with a small cart with bottles of champaign or white wine in ice buckets and poured as asked. I got my first tip there, when a slightly tipsy lady whose glass I was filling lifted my apron front and expressed displeasure at my underwear by pulling the front down below my balls. I understood and dropped them so she could hold and play with my dick for a bit. While doing that she slipped a bill in my tip pocket. When I bent over to pick up my underwear my apron fell open at the rear, so my now bare ass was on display. That got a few appreciative comments and a few do it again later request. Lilly and Sunny were busy handling the people in the main room, so I don’t know who won the bet.
The little bit with the tipsy lady had stiffened my dick just enough so I was now tenting in the front. As I moved pushing my little cart I bent over enough to try and hide it, but that opened the back of my apron for more touches, tips and rubs on and in my ass crack. Then when I stood up to pour a glass, I had to reach around the guest that raised my apron front to the same height as my now almost stiff dick, so it pointed in the face of the guest. The guest would sometimes grab it for a quick tasting, I understood then why Lilly had worked the sugar stuff into the salve she rubbed on it and up my ass earlier. I wasn’t the only one getting the table teasing. Vinny was bringing new things to the table and he was dressed in the same apron I was wearing. He was a bit older though, hairy and with a bit of a pot belly it looked, I thought, kind of silly on him, but the people loved it. Now that the guest had become more relaxed, about half had shed part or all of their clothes before coming in for a snack. Most of the men were high and I heard some talking about Fat man’s new toy, me. My tip pocket was filling nicely, and I was having blast being the center of attraction. One, a comedian I had seen on TV had the longest dick I had ever seen. It was fat also but soft thankfully. When I poured his wine, he said something about sitting on his lap as he stuck his finger up my pre-oiled asshole. Luckily another guest motioned me over for a refill. I stayed as far away from that big dick as I could the rest of the night.

End of the night, I was transformed:
Leaving the table and the few remaining guest to Vinny I moved to the pool area. There should I be asked for a specific drink I would get it from the bartender for the patron. My tip pocket really started working there, I still don’t know how a naked man could stick a bill in my pocket, where did he get it. Rolled in a role a little fatter than a cigarette. Naked women had these little wrist caches they used and the money was also rolled up in a tight little role, but I guess the men pulled it out of their asses or something. People were busy playing everyplace by ten o’clock. Almost everyone had shed their clothes and were fucking, sucking, smoking joints, popping pills or just wiped out enjoying watching the others. A lady called me over and said she needed lubrication, when I started to open my pocket, she said not that kind. She spread her legs on a lounge chair and I went muff diving in one of the nicest cunts ever. Putting my teenage training to work, she got noisy and we drew a small crowd to watch. I was having a good time on my hands and knees with her legs over my shoulders when I felt the cheeks of my ass being pulled apart, and a warm mouth on my asshole, that was followed by the first cockhead of the evening probing in my lubricated asshole. It wasn’t a big dick so he went in easy and was soon slapping my balls with his own. Lady I was oral with orgasmed several times, then pulled away too sensitive for any more. One of the bystanders replaced her by dropping down in front of me spreading her legs. That started a new wetting, this one was younger, more agile and very pretty. I was very surprised that she would be paying for sex. The little dick up my ass had cum and been replaced by a more normal size. It felt good, but wanted more attention than I could give with my mouth full of pussy. Pretty girl had a great moaning whimpering orgasm got over sensitive, pulled me down to hold tight. It was great but I was in demand from others. I turned over pulling my knees up to my chest to see who was fucking me. I recognized him, but following instructions didn’t ask for an autograph.

He finished and it was later now. It had gotten cool by the pool so I went inside. With cum running out of my asshole I went to the toilet room to clean up. Using my little syringe, quick squirt, finger full of fresh lube and I was ready for action again. But while I was on the toilet emptying a voice said didn’t think I’d ever see you again. It was my first timer from La Holla, I smiled and sucked him off while sticking his twenty in my tip pocket. We had a repeat of our first meeting again later that night, for another twenty. In the main room some people were lounging on cushions watching the elevated platform where some woman was acting slutty with a guy playing a piano. Serving a group of five semi naked guys drinks from the bar, one of them kissed me. I had learned from David how to handle this so I went along and returned the kiss in a female manner. Letting him stick his tongue down my throat really turned him on. The other four who had been playing with each other stopped to watch. After a bit of play he rolled on his back, put his legs in the air and I lubed up his asshole for two fingers and my dick. It took some time to get deep in him, so I figured he was new and showing off for his friends. His asshole felt great, hot and very tight, really clenching on my cock. I had fucked a couple of the women while their male friends watched and took over when I pulled out and left, so I still had my first cum load in me. He got it, no rubber, just a very hot ass pumped so full I couldn’t stop the flow. It didn’t help that while I was pumping cum, I was watching Sunny a few yards away with an ugly older man riding his dick. She sure was pretty.

This type of activity went on until 2:30 in the morning when the last naked guest left staggering while being held up by their driver. Vinny had gone earlier so I raided the table for scraps. I had been very active and hadn’t checked my tip pocket which was swelled quite a bit. I was hungry, even though I had a few loads of cum in my belly, I hadn’t eaten to make sure I wouldn’t create any mess in my first time, so I was hungry. At nineteen I hadn’t yet developed a tolerance for alcohol, so had gotten a little tipsy having drinks with the customers. That was wearing off now and I was hungry, tired and as they say fucked out. Lilly found Sunny and came for me. She said she had our pay from Fat man, he was very happy and we could go. Back in the little MG Sunny sat on my lap, by now all of us had bare bottoms open to the world, but even a skin to skin didn’t get a raise in my tired well used body. The cool night air felt great as we rode down the 101 in an open car. Back at Dee’s house we all three in various forms of nakedness raided the refrigerator and joked about what and who we had done things with. Dee woke and joined us, laughing at our tales.
The end:
The next morning I emptied my tip pocket, several bills had notes wrapped with them. I gave the notes to Sunny writing on each the amount of money they were wrapped with. It was Sunday, banks were not open so I put the money in a paper bag until I could deposit it. We formed a partnership sort of. While I worked Sunny would make the calls, find the particulars and make the appointments. She would make appointments from people who were Fat man’s party guest or people who were friends of those we later visited. We worked as a team in the business and as singulars or pairs depending on what was ask for. Sometimes I would be done up as a girl to take to a party, other times dressed as a young male protector, depending on the client and what they wanted. There was no limitation on the services we would provide. Most ask for was cute little Sunny and I dressed up as fairy tale characters. In that mode we acted out a game between us that the customers could direct and join into. Sunny came up with that idea and it proved to be very popular.

My being in the service complicated things on timing. I was subject to an instant deployment to some other place. I still had to do all the things Marine do, so weekends were occasionally taken up with duty that kept me on base both days. It was a fun time and I accumulated a lot of money for that period of time. Then the inevitable occurred, I came back from an assignment with a hole in my perfect will never happen to me body. It resulted in my loss of a large part of my intestines. Placing me in the hospital for six months, during which time a new guy who could be available 24/7 took my place at Dee’s place working with Sunny and Lilly. I had lost a lot of weight, 85 pounds so I was far from healthy and desirable in appearance. I was not willing to have anything inserted inside me if anyone had even wanted to. So I retired and came back home. That period of my life just a fond memory.

Hope you enjoyed reading about my youth.
Wow, what an amazing time! Thanks for taking the time to share all of that with us too!
Amy
(08-08-2022, 01:45 PM)CanuckGirl Wrote: [ -> ]Wow, what an amazing time! Thanks for taking  the time to share all of that with us too!
Amy
Visited Janet's Closet 1st time, wandering among the clothes and accessories brought back a lot of memories.
I'm sure Janet's must be a great place to visit, and someday I hope to make it there.

Also I'm sorry your injury curtailed so much of your fun.

That was very hot to read, by the way.

Way back in the early 70's a guy I knew in school hit the local news as he and a few others were charged in a bit of a sex scandal. I'll use the more polite term, rent boy, but that's what he was doing. Some of us who knew him wondered how he afforded a new car, just a small Ford, but still a new car of his own.
The kicker for many of us was his father was a minister!
A close friend talked about him having sex with women, and he was shocked when I said it likely wouldn't always be women! Most likely not I added.
Amy