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Starting Out


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My senior year at high school would see me turn eighteen years old. As a youth I spent my time developing. I developed my body, my interests, my goals, my likes and my dislikes. Others around me helped to shape my ideas and thoughts but I knew that I was independent. My journey in life would be one of the pursuits of a hedonistic lifestyle, balanced with health and emotion.

Following the celebration and pageantry of my eighteenth birthday I set out on this journey. My mentor had been my mother’s hairdresser Gloria. Gloria was a beautiful single 32 year old woman that I met when she was 24 and starting out in business. On Saturday mornings Gloria would pay me to do odd jobs around her house and clean the yard. She would frolic with her clients throughout the day preparing for whatever social gathering was planned for that night. Sunday’s as I cleaned the pool I would hear the stories from the parties the night before. Sometimes when the event was at Gloria’s I would see the remnants of the night before.

Today I awoke to Gloria and my mother having coffee at the kitchen table. The way Gloria talked with such a sexy throaty voice stirred my loins. Waking up with a stiff morning hard on listening to her made me reach below the covers. The initial sense of satisfaction I felt from stroking my cock was heightened by their conversation. As I slowly rubbed my throbbing dick I was entranced to hear Gloria talking about me. She was asking my mother if I was still a virgin. My mother responded with bewilderment. Gloria pressed on citing examples of my dad’s hijinks at the Cole’s pool parties. From what I could tell my dad showed off his endowment at these parties. It was something that I was shy about in the change rooms and around the pool. I stroked my cock and came in a sock then jumping up to prepare for a shower and lunch.

As I came into the kitchen the room was silent. Had the cat caught the mice at play I thought. I went to the cupboard to make a sandwich. I was dressed normally with a jock strap that cupped my balls and held my cock tight to my body over which I wore spandex tights and cotton work out shorts. The ladies started to jabber away at me. I indulged their mid age prodding but I couldn’t help notice Gloria checking out my shirtless chest. At 18 I had filled out at 6’3″ and 190 lbs. keeping in shape playing very competitive hockey, baseball in the summer, and always in the weight room. We had a good laugh.

Gloria persisted in asking me if I had gotten lucky for my birthday. Blushing I told her that I was more focused on the party and doing well in school but I did have lots of kisses from the girls. As I readied to meet up with my friend Jim; Gloria enquired if I was available to help her late in the day. She had some client bookings through the afternoon and would need me by 5:00 PM. As she talked with me her intent gaze and seductive mannerisms caused me to blush and look away. Gloria was a regular jack off image for me. She was 5’8″ and about 130 lbs. She had firm breasts and a pert little ass.

After my fun physical day I made my way to Gloria’s. I made fast work with the few things that she needed done. She was always so appreciative giving me hugs I thought of her like an aunt. She told me that Norma would be along soon for a waxing treatment soon but I could go for a swim in her pool. I politely declined as I had on only work out clothes. She indicated that would be no problem that in the pool house was as selection of trunks and the blue pair was my dad’s. I loved the fact that she let me swim in her pool. In the summer it was so refreshing. She would often lounge around or take a swim herself. Once when Jim and I were both in swimming she asked me to cover her back in lotion. Jim thought that was so cool.

Off to the pool hut I went to find a pair of swim trunks. I slipped into the blue pair that my father used. They were the Speedo kind and the length of my dong was clearly visible. As I put them back I heard Gloria checking that I was ready. I was startled so I jumped into a big pair of swim shorts as she walked in. I think she caught a glimpse of my bare ass as she walked in. A little embarrassed I asked her what she wanted. She said that since I was swimming she would launder my clothes so when I left I would smell fresh. As startled that I was; I handed over my clothes. She bounced into the house as I jumped off the diving board.

After a few dives I felt like playing a little game. I would start at one end and swim underwater as far as I could. After I tired of this I started to swim laps. This felt so great but it was getting on in the evening and I should catch up with the guys. We were going to go cruising tonight.

I got out of the pool and went to shower and change. In the pool house was a nice fluffy towel to dry off but Gloria forgot to return my clothes. I thought it best to cover up with the towel and go inside. As I made my way inside I was startled to see Norma naked on the treatment table with Gloria between her legs. I didn’t even see Norma come in Norma is a trophy wife to Leo my dad’s best friend. Norma is well made up, wears lots of diamonds and is always got her hair done and wearing nice clothes. Norma had large brown nipple that sat firm on chest. She is over 40 and still in great shape. They must not have heard me come in but as I approached Gloria tore a sheet from between Norma’s legs. My God Norma must be getting her pussy waxed. I had heard about women shaving but I couldn’t imagine that. I retreated out the back door to the pool house. I sprinkled a little water on my hair to make it look wet again and noisily made my way to the house.

As I came bounding up the stairs Gloria passed going to the laundry room. Gloria stopped me and said I should jump in the barbers chair for a quick trim. I did as was told and got up for the trim. I like to keep my hair neat and knowing Gloria sure helped that. Gloria returned with my folded clothes and placed them on the counter. Having Gloria cut my hair was sheer ecstasy. She ran her hands trough my hair as her hard firm mounds pressed against my back I had to keep my hands out of my lap for fear of arousing my cock. As my arm sat on the armrest it seemed that Gloria would slide the v of her cleft into my elbow. The whole time she would talk to me about my plans for the night, my future, what girls did I like typical hairdresser chat but it teased me like hell. Then she asked me why I wear all these clothes she had laundered. I explained that an athlete needs support and can perspire excessively and it was also for comfort. She told me that lots of her boyfriends played sports but it was only me and my dad that dressed like that. I knew where this was headed.

Gloria finished up and offered to show me the latest in treatments that she had been training for. As we were about to go into the treatment room I asked about Norma. Gloria replied back to me that she had left following her treatment. She also enquired how I knew Norma was here as Norma had entered when I was underwater and didn’t greet her arrival. I think I may have gotten caught but I mumbled a poor excuse. Up onto the table I got under the sheet. Gloria explained that she was going to perform a sweedish style massage. She turned on some background music and lit incense.

Gloria began by lowering the sheet to my waist and working my back. She talked more about sex and my virginity. She mentioned that since I helped her she could help me learn how to pick up girls. My back felt great as she moved the sheet to expose my leg. Working up my leg she caressed my inner thigh. I knew she could see my hairy ball sack. Her talk subsided as she rubbed my other leg and prepared to do the front. My cock was hard from the stimulation she was providing I worried how I was going to turnover

Gloria held up the sheet and gave me the privacy to turnover. What a relief but the massive bulge would be evident through the thin white sheet. My cock when hard reaches at least past my belly button. Gloria worked my legs all the way up to the ball sack. Caressing my inner thigh Gloria enquired why I didn’t shave the hair on my genitals. I jokingly told that I was not so good with a razor. She said nonsense that is why an esthetician is trained. Gloria then went to work on my chest; the playground as I told my girlfriends. Gloria then asked me whether I or my girlfriends had oral sex or masturbated. I told her that I love to masturbate but I would never tell my girlfriends As Gloria went along she noted that my nipples were very sensitive like a women’s. I told her that is why it is called the playground. As Gloria worked down my abs and delts I knew the top of my penis was visible. Abruptly Gloria questioned me “If she should just finish me off. I agreed this would prevent me any further embarrassment.

At this point Gloria went to the sink. She was preparing some treatment. She came back and took each ankle and moved it out to a Velcro strap on the edge of the treatment table. With my hands at my side she then strapped them to the table. Gloria told me this would facilitate her treatment to fish me off and the she removed the sheet to expose my rock hard cock.

She was impressed. She commented on how big it was. I told her it was at least a couple handfuls. She said she just had to measure it. No sooner does she have a measuring tape like a tailor than she runs it up my shaft from the pubic bone to the tip and wraps it around the middle. She blurts out ten and one eighth and seven and a quarter. Over 70 square inches of cock. She rgained her composure and lathered up my cock she deftly shaved my cock and balls. Following this she used a witch hazel astringent to prevent razor burn. Gloria asked me if I wanted to come.

I agreed wholeheartedly. Gloria examined my cock running her fingernails along the veins and the underside of the head. My cock was leaking profusely. Her hands felt great on my smooth balls. She would lift one and roll it around and switch to the next while stroking her petit hand slowly up and down the length. Alternating to tweak my nipples she had me turned right on. I couldn’t move. I tried bucking my hips but she would release my cock and I whimpered in agony.

Gloria urged me on asking me if I was going to come. I told her I would but I needed her help. She asked me what kind of help. I told her I need her to wrap her lips around my cock and stroke it hard. She told me that there was no ay she would get that in her mouth. I begged her. She said she would try to lick it. She then pushed me further by licking it like a Popsicle. Her warm tongue and soft lips felt good but I needed more. She asked me if maybe I needed my cock milked. I knew this worked with cows and I hoped it worked with me. Gloria explained that I would have to promise to be a good boy and she would milk me.

Gloria explained that I would need to get on all fours to get milked. She was going to release my restraints and allow me to get on all fours. She told me the rules of my release and that I would be punished if I did not follow the rules. As she released me from the restraints I was able to sit up and admire my newly shaven genitals. As I turned over I lightly played with my balls and stroked my long hard cock vigorously. Oh that felt good. Gloria strapped my arms and legs in place it was strange having my ass up in the air and open. But I was looking for to being masturbated in a new position. Gloria stood in front of me and explained that twice while turning over I had broken two rules and needed to be punished.

Gloria now behind me explained that I would be punished and additional rules added. I was to be spanked 5 times for each offence. If my spankings exceeded twenty then the discipline would be raised to a new level. After each spanking I was to count the spank and thank my mistress. I was only to refer to Gloria as princess. So it looked like I was going to receive 10 spanks from Gloria ah er Princess. How bad could that be it was not like it was my dad. The first spank hit me wow I didn’t know she used a paddle. I had forgotten to count and thank her 5 more. I got through the first five okay. The second five were okay. But we were forgetting about the milking. I asked Gloria to stroke me. Opps I forgot to address her properly.

The next level of discipline. I felt her apply some lube to my asshole. As she rubbed it felt very good. Periodically she slipped a finger into my rectum it took my breath away. Before she returned to finish my spanking she rolled a rubber o-ring down my cock. It was tight as she stroked my cock. My cock was rock hard again. Princess resumed the spankings and I remembered to thank her and call her princess. Gloria then said I was ready to be milked. She slid both of her hands up and down my rod piston like but the o-ring on my cock was tight. The veins of my 10″ cock bulged and throbbed. I could feel the come filling my shaft. She stopped

Ahhh! I pleaded relentlessly. Gloria then probed my asshole it felt good. She explained that she was going to stimulate my prostate. As she hit the spot cum shot out of my cock head. Gloria resumed stroking me and stimulating my prostate as more shots of come shot from my cock head. Gloria drained me completely and I was exhausted. She let me off the treatment table. I thanked her for a wild experience and she said I think it has only begun. She told me she would like to teach me some things that would help me in life. She also said that if I learned to use my cock properly that I would live a very happy and fulfilling life. She suggested that I shower and told me I would get a treat.

I went off to the shower to clean up. As I reflected on my experience I truly felt my life was changing. Shockingly Gloria stepped into the shower completely nude. This is the first time I had seen her naked and been with another women. A smile as wide as the Grand Canyon covered my face as I reached down to warmly embrace. Gloria. My 6’3″ 230 lb frame enveloped her petit 120 lbs. I scooped her under the buttocks and pulled her firm breasts into my chest hugging a sharing a passionate kiss. Shy Troy was being released and I could feel it but Gloria seemed to have the power to rein it in and make me a little boy again.

After we sat and talked in the afterglow we agreed that this project was for only us together. She would not be my girlfriend or me her boyfriend but the emotional attachment would grow. We agreed that I needed work and she needed the help so Saturday was for us. You will hear of her influence in my life as I have grown and lived the full life. Experiences that happened in my life were shaped from this very day. Gloria taught me how to control my power and please women so that I could explore my hedonistic lifestyle. What a journey it is.