Samuel’s Sixteenth Summer
by Fur Babe
Hi, my name is Samuel. Sam for short. I live in a nice home in Scarsdale with my mother. She and my father divorced several years ago and she got both me and the house. She is employed as a fur buyer for a major department store chain and is required to do a lot of traveling as part of her job. My father is the art director at a major advertising agency. He also recently married his 24-year old girlfriend.
It was the beginning of summer after my sophomore year in high school. I turned sixteen last month and over the last year I started growing. I was always the shortest guy in my class, which made it really hard to get the girls interested in me. After all those years of being called shrimp, I suddenly was over 6′ tall and starting to fill out, including my penis. I got a car for my birthday and I was looking forward to my vacation. I had visions of finally have a sexual affair with some gorgeous girl, leaving my virginity behind me.
My mother was scheduled to go on an overseas business trip for the summer months, and she had agreed to let me stay alone at home. I would just have to check in every day with my dad, who lived about a mile away.
I was sitting in my room alone, watching a porno tape that my friend Peter had lent me, masturbating myself to the thought of Alice, a girl at school who had been giving me the eye lately. I was almost ready to climax, when my mother walked in and caught me in the act. She gave me a really angry look, demanded that I give her the tape and told me it was inspection time. She went through my desk, my bureau drawers and my closet, finding my stockpile of skin magazines in the process.”I thought so,” she announced as she took the tape and the magazines and stormed out of my room. All my fantasies of conquest came crashing down to earth. When mom came back in about an hour later, she announced that instead of being trusted to be on my own, I would be spending the next two months with my godmother, Pamela. “Oh, not there!”, I begged. “She lives in the middle of nowhere! There won’t be any girls around for miles, no beach, no malls, no nothing!”. “That is exactly the point. No temptations. It will give you time to think about your sinful behavior, young man.” Mom was great, but a bit too old fashioned and puritanical. It also wasn’t the first time she had caught me masturbating. She had warned me, but with my teenage hormones, it was too hard to resist doing it.
Not my godmother! She was at least 35 years old, and I hadn’t seen her in at least six or seven years. I remembered her being pretty, but really fat and she was just so old! I begged and pleaded, but my mother wouldn’t budge. So two days later I was on a plane to Aspen, Colorado feeling totally depressed. My mom said that she had told Pamela about my behavior and had extracted a promise from her to always keep a close eye on me. I thought I would die, this old lady knew about my masturbation and now she was going to baby sit me for the entire summer. I was sure that my life as I knew it was over.
I didn’t recognize Pamela when I got off the plane, but she knew me from the photos my mom sent. When she walked up to me, I nearly passed out. Oh, she was 35 all right, but otherwise, my memory of her was completely erroneous.
She was tall, almost as tall as I, even without heels. She had incredibly long legs, and what a body! She gave me a sexy evil smile and said, “I guess you didn’t recognize me because I’ve lost a little weight since you saw me last.” A little was an understatement! She was well proportioned! My godmother had the most provocative body I’d ever seen, noticeable firm breasts, a full, round backside and a gorgeous face! Her hair was shoulder length, a dark reddish brown and the biggest dazzling blue eyes I’d ever seen. Her face was impeccably beautiful and she had this great mouth that I immediately imagined sucking my penis. I had an instantaneous erection, right there in the airport, and my not wearing underwear, she spotted it right away. Pamela was wearing jeans and western style boots and a short fur jacket. She got a stern look on her face and whispered to me, “I’ll take care of you later, Samuel, I promised your mother I’d teach you to obey.” God, I hate it when adults call me Samuel and talk that way to me. Pamela didn’t say another word to me as we drove to her place, which took about 30 minutes. She just kept this really strict, somewhat forbidding look on her face and that immediately shrunk my penis.
We finally arrived at her chalet, which was somewhat rustic, but nice. It was built into the side of a hill and hidden off to one side there was a swimming pool and a tennis court. The chalet had the living and eating areas downstairs and two bedroom suites, opposite each other, upstairs. She immediately took me upstairs, so I did not get a look at how the first floor was furnished. I was told to place my bags in the room Pamela pointed out to me. As soon as I entered it, I realized that the door on my room was held open by a locked bar across the top of the door. My godmother got a rather wicked evil look on her face and said, “I did that so that you wouldn’t be tempted to close the door and masturbate. I’m going to be keeping a close eye on you, Samuel.” She told me that I might as well unpack and that the door will be open the entire summer. Oh, gee, I thought, she works at home, too. I’ll never be alone at all. I thought that it would be a really miserable summer for me with no action at all. I couldn’t have been more wrong.
Pamela called up to me shortly after we arrived that she had forgotten to pick up some things in town and that she’d be back in about an hour, and that I should behave while she was gone. When I heard her car leave, I hauled out the skin magazines that Mom hadn’t found and I was able to hide in my suitcase. Feeling safe, I whipped out my penis and started to masturbate. In less than a minute, my penis was at its full length and I was stroking it furiously. The women in the magazine were really hot, all spread open and fingering their juicy clitoris. I swear that one of them looked almost exactly like my godmother Pamela. I was having such a good time masturbating and wanted to really enjoy myself, so I decided to slow down and to take my time. The pictures were fantastic and the sweet sensation of masturbating had me fantasizing about all of the things I could be doing to these women. I also thought about breast fucking Pamela, my huge penis forcing its way up between those big luscious breasts, poking my penis deep into her mouth on every upstroke choking her on it. My love juice would squirt into her mouth and I would make her swallow every thick drop of it. I had my eyes closed, savoring the idea of making my sexy godmother my lover, when I heard a tapping outside my room. I dropped my penis instantly and opened my eyes.
There stood Pamela, dressed in this tight black mink teddy. Over it she was wearing a matching black mink robe lined in sheared white mink. The teddy had no cups, showing off breasts that were even bigger than in my dreams. Her nipples were hard, standing straight out from her breasts. As my eyes moved down her body, I noticed that the teddy was slit at the crotch, exposing her cleanly shaven pussy. She arched her back and deliberately showed off her long swollen lips. Her long, long legs were encased in black seamed stockings. Wearing four inch spike-heeled shoes, Pamela became taller than me. I was a bit confused by her outfit, but couldn’t help thinking how seductive she looked in it. Pamela had something in her hand, which I couldn’t quite make out and had a ferocious expression on her face, totally unsmiling but with a strange gleam in her eyes that made me wonder what she had in mind.
She snarled, “I knew that you’d be beating your nasty cock the minute I left, so I came right back and saw you jerking it. Now I’m going to give you the education you so richly deserve, little boy.” Little boy? Me? I scoffed at her for a moment, then realized that I was in no position to protest. She’d tell my mom everything and I’d be grounded for life, but thought that I might have a chance at getting out of the punishment she had planned for me. I stood up and tried to run past her out the bedroom door, but my old godmother was much faster and stronger than I’d anticipated.
Before I could get past her, one hand grabbed a handful of my hair and she jerked me to an abrupt stop. Before I could recover, her other hand was firmly around my testicles and squeezing them together. Her nails were digging into the back of them. I had never felt so much pain so quickly in all of my life. I was completely helpless. She opened the top of my pants and they dropped to the floor. Then with her free hand she ripped my shirt open and took it off and dropped it on the floor. I had been stripped naked except for my shoes and socks. She then led me across to her bedroom, and made sure I got a good view of it. There was fur everywhere. The king size bed with the oversize silver fox bedspread and a smaller white colored rabbit spread over part of it. The bed was an old fashioned four poster type with a canopy made of blue fox. The off-white sheared beaver drapes, the white mink covered chairs and couch. The bedroom was completely decorated in fur. I was somewhat familiar with furs because of my mothers job, but I only considered fur coats and things. I never dreamed of seeing furs used in such a way. Pamela was totally immersed and surrounded by furs.
Pamela led me over to the bed, released me, threw me onto it and before I knew it, she had my wrists strapped to the headboard with the mink lined fur cuffs she’d been carrying. My legs were next, she removed my socks and shoes, and before I knew what was going on, she had my ankles spread and strapped to the footboard. She stuffed some fur into my mouth and then stood back to appreciate her handiwork. She then placed another silver fox spread over me, so I was totally enveloped in fur. The only exposed part of my entire body was my face and she was rubbing a heavily perfumed mink boa across it. The feel of the fur and the smell of the perfume was driving me crazy. Every time I tried to move, I could feel the softness of the fur against my body. I have never felt a sensation like this before, It was all I could do to just lay still. My godmother had a diabolical grin on her face, and told me that she would be teaching me to control myself, lightly pinching her hard nipples, then mine, as she spoke. My penis was rock hard from the moment I was thrown down on the bed, both from the sensation of the fur against my body, her touching me and just watching her touch herself. They did nothing to help me reduce the urge to have an orgasm. Pamela then kicked off her shoes, crawled onto the bed and under the fox cover like a cat and looked deep into my eyes with her big breasts brushing against my throbbing penis. She explained that she would be teaching me how to properly have sex with a woman and how not to have an orgasm unless I was given permission. I swear that when she said that, my penis felt like it grew another inch. I kept thinking how weird this all was, but at the same time I was being turned on by this bizarre event. The furs and her crouching above me, in or out of that outfit, wasn’t going to let my penis get soft. She reached for my testicles and strapped something tight onto them, saying that it wouldn’t allow me to have an orgasm, no matter what. It didn’t hurt, but felt tight and very soft around my swollen testicles.
Pamela then got up and picked up my clothes and placed them in what was to have been my bedroom. She just left me lying on the bed on two fur spreads with the third one covering me. I could not decide which felt better. Should lie still and feel the softness of the furs against my skin or to try to release myself and feel the fur against my body as I moved. Either way the feeling was sensational. She unlocked the bar keeping my bedroom door open, closed and locked my bedroom door. Coming back to her bedroom, she told me that I would not be needing those things while I was staying with her. Then she looked at me and said, “These are the rules you will follow. First, your body will always be clean shaven. Next, you will always wear makeup and also the clothes I want you to wear. I want you to always compliment my appearance times. Do you understand?” I thought, there is no way I going to let her do that to me. I wasn’t going to let her dress me up as a girl. I shook my head no as defiantly as I could.
My godmother then took off her robe and teddy, got back on the bed, sat on my chest and slid up toward my face. Pulling the fur out of my mouth as she said, “Now we’ll learn all about eating pussy, open your mouth.” She pushed her smooth pussy against my open mouth and told me to suck her hard lips. Gently. I obeyed, but I guess I didn’t do it quite right, because she pressed her pussy firmly against my face, practically smothering me, and told me to get it right or else. She went on to sit there in the same position for about half an hour, telling me how to find and lick her clitoris, into and around her swollen lips, how to suck and lick her at the same time. Finally, when I was dizzy from the taste of her love juices and my tongue was starting to cramp up, Pamela tightened her firm thighs against my face, forcefully shoving her pussy into my face and started to move her hips vigorously in a steady motion, finally climaxing loudly with an orgasm and flooding my mouth with her cum. She was literally gushing on my face! I was amazed and so turned on at the same time, I just loved the taste of her cum. She made sure I swallowed it all and then she made me clean up anything remaining with my tongue.
By now my penis was throbbing hard and I was dying to be allowed to have an orgasm. When my sexy godmother finally finished and fell back on the bed, panting, I breathlessly begged her to let me have an orgasm. She only laughed at me and said that I would do that when she was satisfied. She then again asked me if I were ready to accept her rules. I again refused.
Pamela now swung her leg over my body and went on to straddle me, up on one knee. She took my penis in her hand and began to masturbate herself with it, rubbing my swollen head on her still hard lips. She threw her head back and got into it, using my penis like a dido, occasionally teasing me by sliding just the head into her pussy and squeezing it with her strong muscles, then taking it out again. All the time she was moistening it. Then she stroked my penis with a sheared beaver muff, which produced the softest, most erotic sensation I had ever encountered while drying it off. I was practically crying from the frustration. I couldn’t feel the difference between her body and the fur any longer. And Pamela just kept switching back and forth, moistening and drying. I could feel how badly my penis was trying to have an orgasm, but nothing would come out because of the strap around my testicles. I begged and begged some more, promising her anything if she would just get me off. I felt I could have had multiple orgasms, many times the normal amount, but just couldn’t. She made me promise that I wouldn’t masturbate while I was with her, and that I would live by her rules while I stayed with her. I couldn’t stand it any longer and I shouted out that I wouldn’t dare disobey her and obediently live according to her rules. If she would only give me some relief, I would become hers for the summer.
Pamela returned to sliding my hard penis up and down her smooth wet pussy, moistening it, explaining my duties to me. I was to be ready to please her any time with my penis or mouth or fingers, servicing her until she was completely satisfied. I would also always be appropriately dressed and made up. I nodded my head in agreement just as she mounted my penis, sliding down the length of my thick shaft with that incredible tight hole. She turned the tape player on which started playing Ravels’ Bolero as she began to rock her hips and moving up and down my penis keeping time with the music. Starting with slow short strokes, she kept time with the music. As the music became faster and louder, Pamela moved faster and longer, simultaneously feeding me her nipples one at a time, pushing them into my eager mouth. Having no other choice, I just sucked and sucked, loving every moment of my first fuck, but still not able to climax. The music kept getting faster and louder and Pamela was moving her hips faster and taking longer strokes keeping time with the music. I kept shouting and screaming for relief, but without success. Pamela was totally engrossed with the music and the joy I was forced to give her. The music was still getting faster and louder as Pamela was stroking faster and longer. My screaming was also now also keeping up with the music, but I was receiving no relief.
Finally, as the music was coming to a finish, I could feel her pussy tighten around my penis, beginning to throb with yet another orgasm. She was starting an orgasm that had an intensity I could not even imagine. Her moaning was coming from deep within her body. Just then, she reached back and removed the strap from my testicles. As the music finished, we both had simultaneous orgasms. I never had cum as violently as this in all of my masturbating days and the emotional experience of actually having sex was fantastic. Pamela had taken me on a voyage beyond my wildest imagination, something that was at a level that I could not believe existed. I was exhausted and Pamela collapsed on top of me as well. She reached up and released my hands, then my feet. Then she wrapped her arms around me and pulled me close to her, my breasts and my lips against hers. We then rolled back and forth wrapping the fur spread around us. She then chuckled and told me I had just been transformed from Samuel, the little boy, to Sam, the man. Then she apologized for her roughness, and I insisted that I didn’t mind one bit. A sexy evil grin appeared on her face.
After a couple of hours wrapped up with each other, Pamela got up and told me that it’s time we got started to get ready for dinner. For the first time I realized what I had agreed to and that Pamela was going to hold me to it. I started to protest, but she interrupted me by saying, “I don’t think you want to be tied up again. I’ll offer you an other choice which is leaving right now, just the way you are, no clothes, not anything.” Again I realized that I did not have a choice, so I followed her into her bathroom, where she totally covered my body with a sweet smelling rich white cream and thoroughly rubbed it into my skin. She told me that it was absolutely necessary for me to remain absolutely still. She would give me directions so I would be in a proper position and also directed me to hold my skin so it was tight. Pamela reached into a drawer and pulled out an old fashioned straight razor. She showed it to me and asked if I had ever seen one before. I responded that I only had seen them in some old movies. “That’s good enough. You know what it is, what it supposed to do and what it can really do. I am going to shave you. Do you believe that is all I am going to do?” Her admonishment to me to do exactly as she directed took on a new meaning for me. Then she took the razor, honed it with a leather strap attached to the dressing table and shaved every inch of my body. I was frozen with fear and when Pamela finished she said, “I’m glad that you decided to really trust me. I wouldn’t want to hurt you.” Then she rinsed me off in the shower. Dripping wet, she made me look at my cleanly shaven body. I was cleanly shaven, except for a small heart shaped patch right above the base of my penis. “That shows that you belong to me,” she stated, admiring her artistic handiwork. Noticing the redness around my sensitive areas, she applied some lotion and gently rubbed it in to the skin, which relieved the pain caused by the shaving. Pamela then drew the bath complete with scented bath oils. We then preceded to bath each other and then dried each other. She then powdered me down, first the back and then the front. Before I could protest, she was finished, gave me the powder and said, “You’re turn.” She made me powder her, directing me so I would not overlook and miss any part of her body. Pamela noticed that I was hard again and gave me an admonishment about having an orgasm without her permission. I apologized and told her that I could not help it. She then gave me that stern hard look and it immediately shrank. She then smiled and said, “See, you are learning already. If you don’t follow my wishes you know that I can make you suffer. But don’t worry about it, I won’t let you suffer to long. Only until I’m ready for you.”
Pamela now led me back to the bed. She went over to a chest of drawers and came back with two pairs of white mink trimmed lace panties. She ran them up and down my legs and again the feel of the fur against my skin became overwhelming. Pamela gave me a pair and told me to help her put them on. As I pulled them up, she wiggled her hips back and forth and told me to pull them up so they were nice and snug. She now held the second pair and told me to put them on. The expression on my face must have told her that I was going to object. I was, but decided not to when I saw that expression on her face.
I instantaneously reviewed my situation. First, I was going to be here for the next two months. There was no question about this. Next, in less than one day, I was no longer a virgin and Pamela has shown me more about having sex than I ever imagined. There was so much more to it than just the physical act. Then I also found that I was beginning to like the way my body felt. The newly found softness of my shaven skin was giving me a pleasurable sensation. I had trusted Pamela when she shaved me. She could have really inflicted serious pain when she shaved me with the straight razor. Finally, I took a chance that there would other experiences. Pamela surprised me at every turn, right from the moment we met at the airport. I was sure she had more to teach me. I made a major decision, in fact, it was the first major decision I had ever made.
She started to admonish me and I placed one of my fingers across her lips to stop her. I said “I’ve come this far, you have humiliated and outsmarted me from the first moment we met. I surrender. I’m going to be yours.” She just looked into my eyes and again gave me her sexy evil grin. As she was pulling my panties up, I heard her whisper in my ear, “Thank you. Now wiggle the hips so the panties will fit nice and snug.” I was now completely hers. For the first time since I met her, my reply was a sexy evil grin on my face. I would follow, obey and serve without question, as I tried to wiggle my hips the same way she did, so she could pull my panties up nice and snug.
Samuel’s Sixteenth Summer – Part 2
Well, I had now been introduced to having sex with a woman. I must admit Pamela was really good and I thoroughly enjoyed the experience with her. Since, I have to spend the rest of the summer here with her, I’ll go along with having sex with her, but this stuff about wearing panties is for the birds. I started thinking about ways to get around this problem, but Pamela had her own ideas and was anticipating my rebellion. She realized that I was lying to her when I said I would surrender and become hers.
Pamela looked at me and said, “It’s been a busy day for you. Let’s just get casual, have a light dinner and take a drive around town.” I nodded in agreement. Pamela said, “OK, let’s get started.”
She went to a closet and came back with a pair of shoes. She said “Your feet look about the same size as mine. Let’s try these on.” In her hands were a pair of white women’s shoes with 5-inch stiletto heels. Before I could say anything, Pamela sat me down on the makeup bench and put nylon stockings my legs. “They are just to protect the back of your feet,” she said. Then she put the shoes on my feet. I felt the heels pop into place. She then tightly buckled the ankle strap on each shoe. She then stood me up. I felt very strange, not being accustomed to the added height of the heels or the way the weight shifted in my feet. She then went to the closet and came back with a huge silver fox coat that she slipped on me and buttoned it up. Pamela then motioned for me to take a step. I took that step forward and almost fell on my face. Pamela caught me and helped me regain my balance. She told me that the heels will take some getting used to. I wanted to look at my feet to see what I was doing, but the coat kept me from seeing my feet. I was told to keep my head up, my weight on the balls of my feet and to take short steps. Pamela steadied and guided me as I walked back and forth across the room. She complimented me as I became surer of myself. “Try putting one foot in front of the other,” she said, “It will allow your hips to move in a more rhythmic fashion.”
After about ten minutes of walking around the room, she told me to take the coat off and to sit on the makeup bench. The heels arched the foot in a manner that I was not accustomed to and made sitting down very uncomfortable. Pamela said, “You’ll get used to it after a few minutes. Starting now, you will always wear 5-inch heels unless I tell you otherwise. There is a wide selection of heels in the closet. Also starting now, you will always wear a fur coat or jacket fully buttoned when you leave the bedroom. Meanwhile, let’s get started on your makeup. Watch what I do very carefully. You will do your own makeup after tomorrow. I’ll keep it simple this evening, just a wig, some eye shadow, foundation and lip stick. Tomorrow we will do the complete makeup do over.”
Going over to the closet, she returned with a round box. Opening it, she pulled out a golden brown wig. It was very full and the hair was very long. Placing it on my head, she adjusted it making sure all of my hair was tucked in underneath it. I felt the hair reach down my back, across my shoulders and against my face. Taking a brush, Pamela began brushing it out and shaping the style she wanted. One side came across the side of my face and against my eye. The other side was brushed back over my shoulder. She told me to shake my head so the hair would move about. Her smile showed she was satisfied with the way the hair looked and moved.
Next, she applied foundation to my face, making sure to cover any hair stubble and other blemishes. Then she applied a blush and blended it in using a brush. Now it was time to do the eyes. Pamela told me to hold very still. She then applied an eyeliner to the edges of my eyelids and then mascara to my eyebrows. Next was the soft blue shadow over my eyelids and under my eyebrows. The final step was to trace the outline of my lips with a bright red lip pencil. She then produced a fiery red glossy lipstick and brushed in the remainder of my lips with it. I was then instructed to carefully press my lips together a few times. The lipstick felt cool and soothing on my lips, it was no wonder women enjoyed wearing it. Stepping back, she admired her handiwork and told me to go over to the full length mirror and look at myself.
Standing up, I immediately became aware of the heels again. Remembering Pamela’s instructions, I slowly started to walk over to the mirror. “Very good. You’re getting used to them. Like a baby, your learning to walk again,” Pamela commented. Looking in the mirror, I was surprised to see a feminine face looking back at me. In a few minutes’ Pamela had completely transformed my face into one of a female beauty. She then told me to walk over and sit on the bed. With every step I took, I became more secure and comfortable wearing the high heels.
Pamela said, “First, let’s take these shoes off. I think you did very well for your first experience.” Then she went about the bedroom and closets, coming back with an armload of clothes. She then removed the nylon stockings I was wearing and gave me a pair of white nylon stockings. I was shown how to roll them up into a donut, extend my foot and to put them on. She said, “Be careful, you don’t want to snag them and cause them to run.” I carefully put the stockings on and as I was doing this Pamela told me to keep the seam straight and centered on the back of my leg. After a few minutes I had finished putting on the stockings. Pamela then told me to stand up. First I felt funny standing without the heels, although I had only wore them for a short time. I was then given a fur trimmed white lace garter belt, which matched my panties. Under Pamela’s tutelage, I put it on and attached the garters to my stockings. She then scrutinized my work and adjusted the garter straps so my stockings were held tight.
Next, she gave me a pair of silver blue mink shorts and told me to put them on. As I put my foot into one leg, Pamela burst out laughing. When I stopped and looked at her, she just kept on laughing. After a moment she regained her composure and said, ” You are putting them on backwards. For women the zipper is always in the back.” I looked at her and after a few seconds I also broke out in laughter. Removing my foot, I turned the shorts around and lifted them up into place. But Pamela’s desire for perfection caught a slight flaw. “Hold it,” she said, “something’s wrong.” With that she reached into my panties and pushed my penis down so it went between my legs. “That’s better. Now reach back and pull the zipper up.” I had difficulty reaching back, but I managed to get the zipper pulled up. I could not however get the one button at the top of the shorts. Pamela smiled and said, “let me button it for you. You will soon be able to get it yourself.”
The last piece of clothing was the blouse. The one she selected was a short white mink blouse. When I put it on, it was obvious, even to me, that it was not going to work. Pamela told me to take it off as she went back to the bureau to get more clothes. She came back to the bed with a white fur bra, inserts and a dyed dark blue mink blouse. She showed me how to put on the bra and closed it for me. Then she placed the inserts into the cups and did some final adjustments to the straps. I instantaneously had size 36 D breasts, the same as Pamela. She had me bend over, jump up and down and twist side to side. Pleased with the way the breasts moved, she handed me the blouse and I put it on. Since it was Pamela’s blouse, the breasts gave it the proper look. Pamela then tied the bottom of the blouse together so that my midriff was visible. She then closed one button and adjusted the blouse so the edge of the bra was visible. The only thing missing were shoes and Pamela produced a pair of sandals with 3-inch heels. She walked me over to the full length mirror and I was greeted by a gorgeous young woman looking back at me. Pamela turned me around, stood back looked at me and gave me a sexy evil smile suggesting her approval.
Having finished with me, Pamela started putting on her makeup. Again she told me to watch carefully as she applied her makeup. I watched as she methodically went through the makeup process, Starting with the hair, the eyes, the foundation and blush and finally the lipstick. Then she put on a similar outfit as mine, except for the bra. Pamela had no problem filling out her blouse. Slipping on a pair of sandals she said, “Put on your fox coat, let’s go downstairs and have something to eat.”
Aside from my arrival, this was my first venture to another part of the house. I quickly became accustomed to the 3-inch heels on the sandals, until I reached the steps. I tried going down one step and quickly retreated. Pamela smiled and said, “you thought it was easy, didn’t you.” She then took me by the arm and showed me how to descend a flight of stairs. Once I made it down, she gave me a quick tour of the downstairs area and the pool and tennis court. We ended in a small dining area adjoining the kitchen. Pamela told me to slide my coat off and slip it over the back of my chair.
Pamela got a spinach salad out of the refrigerator and served it along with some white wine. I looked at it strangely and Pamela quickly distracted me by saying, “I’ve given you a rather difficult time today. You must have many questions about it.” I said, “Only one really. What’s with this thing of getting me all dressed up like a girl? Are you trying to make a sissy slut boy out of me?” Pamela smiled saying, “Not at all. I’m just going to follow your mothers request to stop you from masturbating. Unfortunately she did not ask how.” Responding, I said, “That part is easy, you gave me a good lesson in that this afternoon.” “You did not get the full understanding of what I told you,” was her reply. ” I told you I was going to teach you how to properly have sex a woman. You think having sex is just mounting a girl, pushing your penis into her and having a good time for three or four minutes. There is more to it that. You are going to learn what a young woman goes through for you, so you can have a good time, ” she continued.
“I don’t understand” was my response. Pamela responded, “A young lady takes the time to prepare for sex. She wants the experience to last. She wants it to be an emotional and also a physical experience. The way you will learn this is to actually experience the things that a girl does to prepare herself. The process is simple. Dress like a girl, you then feel like a girl and then you will think like a girl.” The learning comes by always being aware of the clothes and makeup you are wearing and seeing that it is always properly worn or applied. She then continued to tell me about the many different things that she would be making me aware of. When our conversation ended, I noticed that I had finished the salad, but still did not understand the full meaning of what she had told me.
We cleaned up, and started to leave, when Pamela admonished me about going out without checking my makeup. It seems my lipstick was smudged while I was eating. Having repaired my face, we started to leave again when she told me to go back for my fur coat. Then it was to go back for my purse. Finally Pamela held up something. I looked and it was the 5-inch stiletto heels, which by this time I put on without any argument. When we got outside, I started to get into the car and Pamela again burst out laughing. I stopped and looked at her. When she regained her composure, She said, “Not that way. You’ll end up flat on your ass. Turn around and first sit, then put your legs into the car.” I decided to continue getting into the car the way I normally did and when I put my foot into the car, I could feel myself starting to fall. Again Pamela was right, so I turned around and entered the car as a lady. Pamela got behind the wheel and as we started she said, “There’s more to it than you thought, isn’t there.” With that she put the car into gear and we started the tour.
We went up and down some twisting bumpy mountain roads. I think Pamela did this on purpose, since I could feel the fur rub against my skin with every bump. I was totally aroused by the time Pamela reached a paved road and started toward town. I was surprised at what I saw when we got into Aspen. It was a very sophisticated town. There were clubs, restaurants and many upper scale shops. Pamela asked me if I wanted to go into any of the shops. I told her no and she replied that it was all right. Shopping will come soon enough, Today has been a busy day for you.
We drove around for a while and then headed back to Pamela’s place. We went inside and Pamela made me walk up the stairs in the heels and wearing the coat. The first two or three steps were tricky, but I slowly gained my confidence and made it up the stairs. We went into the bedroom and started to undress each other. Pamela helped me with the wig and shoes. She then showed me how to remove my makeup and also removed hers. Then she decided to have another sexual encounter and we were back on the bed. After two orgasms, we then wrapped our arms around each other and ourselves in the fur spread and went to sleep.
I dreamed that I was having sex with many gorgeous maidens and they were meeting my sexual needs. I abruptly awoke, became aware that I was erect and found that Pamela was gently fondling my penis, gently stroking the underside. “Good morning. I’m glad to finally see you awake, ” she said as she jumped on my penis and started to pump away. I was told it was just a before breakfast quickie to start her day. We then got up and showered. She then told me that she had put out my morning outfit and I went into the bedroom and found a pastel mink bikini with a matching wrap around skirt and jacket. Next to it was a pair of open back heels. Pamela came into the bedroom and we helped each other into the matching outfits and I put on the heels. She told me that she selected these heels since with the open back I did not have to put on stockings.
The first challenge of the day was going downstairs in the 5-inch heels. Pamela encouraged me by reminding me that I went down stairs in 3-inch heels and up in 5-inch heels yesterday. I also noticed what she did not tell me. Unlike the night before, the sandals did not have an ankle strap and I had to figure out how to keep them on. I was finally able to very carefully manage getting down the stairs. For breakfast we had juice, a toasted muffin and tea. Pamela gave me a large over the shoulder bag to carry and we then went out to the pool area.
The pool was fairly large and the deck had heavily cushioned lounges. I was told to put the bag down, take off my jacket and skirt and to follow Pamela into the cabana. Once inside, she pointed out the one piece swim suits that were to be used for swimming and the storage area that contained the towels and several fur spreads. She told me to take two of the fur spreads and some towels out to the lounges. I chose two crystal fox spreads and grabbed some towels returning to the lounges, where I placed the spreads on two of the lounges. Pamela told me to apply suntan lotion on her body. She in turn applied the lotion to my body.
She told me to lie down on my back and then sat next to me on the lounge and started to manicure and apply false fingernails to my nails. Finished with that task, she took a nail file out of her bag and shaped my new nails. When I looked at my nails, which now extended 3/4 of an inch beyond the my fingertip. By this time about half an hour had passed and Pamela took a towel, wiped down my body and then told me to turn over onto my stomach. First she applied suntan lotion to my back. Then she took my hands and applied polish and sealer to my nails. When she finished and the nails dried about another 40 minutes had passed. Time to turn over onto my back. More lotion and then she started work on my toes. Then it was back on my stomach until the toes dried. When the toes were dry, we put the towels and spreads away and returned inside.
Back in the bedroom, Pamela decided that it was play time before she started doing my hair and makeup. We went to bed and the first thing that happened was that I had an orgasm almost immediately after we started having sex. Pamela was not pleased with this, admonished me for my lack of discipline and again put the mink strap around my testicles. She then started playing with me for about an hour using both her body and the furs. Again I was driven into a state of both pleasure and pain as I wanted to have an orgasm, but was unable to do so. She was riding my penis until she had one orgasm, then kept right on going and was ready to have a second orgasm when she removed the strap and we both had orgasms. After resting for a short time, she was ready for more. I thought I was finished, but Pamela showed me a few new uses for fur that inspired me to have additional orgasms. When she was satisfied, she took me into her arms and as our breasts and lips came together, we wrapped ourselves in the fur spread and rested.
After a while, she got me up and started on my hair. My hair did not provide her with too much of a challenge. I normally wore it rather long. She combed it out, parting my hair in the center and then combed the hair in front down over my face. Taking a pair of scissors, she trimmed the hair into a feminine style, then she walked over to a mirror and asked me what I thought. I was surprised and speechless when I saw her handiwork on my hair. I also received another surprise. The outline of the bikini was very noticeable on my body that had gotten a nice tan. Pamela saw me staring and said, “Oh, you must really like your new bikini line.” Before I could say anything, she started applying a lotion to my hair and also onto my heart of hair. After about twenty minutes, she put me into the shower and rinsed the lotion from me. Then she dried my hair and combed it out again while applying hair spray to hold it in place. When she was finished, she held the mirror up and showed me the results. I was now a blond. It was the first of many colors my hair would become over the summer, since Pamela made it a point to shave me and color my hair once a week.
Since I did not have an orgasm while I wearing the fur trimmed lace panties or the bikini, Pamela decided that I should start wearing fur panties. She gave me a pair of white beaver panties and after I put them on she had me put on both my makeup and hers. The makeup items felt strange in my hands. I realized that the long fingernails made it difficult putting the makeup on, but Pamela guided my hands through the entire procedure with her steady hand.
An evil smile now appeared on Pamela’s face. “Now comes the fun part,” she said as she went to the closet and came back with the dresses we going to wear that evening. First came the matching fur bra with the inserts, the stockings and garter belt. Then she had me step into a beige sheared mink petticoat that was fastened about my waist. Next was the dark brown mink evening gown that flared out when worn over the petticoat. The top was tightly fitted and was complete with a high collar, puffed shoulders and with 3/4 length sleeves. It was closed from the back with laces which Pamela tightened and laced. Then she buttoned the overlapping fur that hid the laces. Finally she helped me put on the shoes and told me to walk around the room while she got dressed, so I could get accustomed to the weight and feel of the gown. She also dressed in a mink gown, except hers had an open back and was sleeveless. We both put on evening gloves and ankle length light brown mink fur coats. Pamela’s coat had large patch pockets and mine did not have any pockets. As we started to leave the bedroom, she made sure I was carrying a small evening purse.
Another one of her subtle traps was about to be sprung. When we got to the top of the stairs, she casually raised her coat and gown and went down the stairs in her heels. I stopped when I got to the top of the stairs. I was waiting for some sort of help, but none was forthcoming. The only response from Pamela was to stop fooling around and get down stairs for dinner. The coat and gown made it impossible to see where I was placing my feet. Watching Pamela, I knew I would have to raise the coat and gown while still holding the purse, so hopefully I would not trip or fall. It also meant I had nothing to hold onto as I went down the steps. I slowly felt for the first step and slowly lowered my foot. As I brought the second foot down, I realized that all of the furs together with the heels made going down the stairs without falling almost impossible. Finally after about ten minutes I reached the bottom of the stairs. Pamela commented in a rather haughty manner about the length of time it took me to come down the stairs.
We had dinner and a casual conversation. Pamela made no mention about the difficulties she making me endure. She kept encouraging me to have more iced tea, using the pretext that I had to keep up my body fluids. We just kept talking until I realized that I had to go to the bathroom. As I closed the bathroom door, I realized my next dilemma, How to go to the toilet wearing all these clothes. Without going into any details, This task took me an abnormal amount of time, and I am proud to say that I successfully met this challenge. When I came out of the bathroom, Pamela had a big evil smile on her face. With it, she was telling me that she got me again. The final ordeal of the evening was going back upstairs fully dressed. Again, it was a matter of trusting where I placed my feet, and going up the stairs very carefully. Finally making it up to the bedroom, Pamela was waiting for me in a chinchilla robe. She carefully undressed me, checking that all of my clothes were properly in place and that my panties were not wet. After the evening’s ordeal that I was forced to encounter I was about to ask Pamela if we could forgo sex tonight. My hope was short lived when Pamela, being satisfied that I met her challenges for this evening said, “Well just don’t stand there. Move your backside into bed. It’s time for some serious sex.”
The next two weeks went by with my obeying and servicing Pamela. She maintained absolute discipline, chastising me every time I missed even the smallest detail. I was beginning to get used to wearing makeup and furs around the house, and Pamela took me to town with her at least three times a week. We would go into various women’s shops looking at lingerie, clothes, furs and makeup. I would have to look at these things with her usually along with a salesgirl. I detested this, but Pamela showed no mercy.
One morning I awoke before Pamela. Looking at her sound asleep, I saw a way to get back at Pamela. I was going to wake her up the same way she had been waking me up. I slowly and gently started rubbing her breast with fur and gently tweaking the nipples with my fingers. Her nipples responded by getting hard, but Pamela did not awake. I moved my hands and the fur down to the inside her thighs and I could feel her relax. I gently guided her so she was on her back, keeping the fur moving up and down the inside her thighs. Her pussy was becoming wet and soon her body showed the first signs of an orgasm. Since it was coming so quickly, I decided to take it orally and positioned myself accordingly. I moved the fur back to her breasts and Pamela started moaning in her sleep. Her body was really trembling and her hips were beginning to move. I took her hips into my hands and placed my mouth over her pussy and continued to encourage Pamela. All of a sudden Pamela awoke, but it was too late. Before she could say anything, she was having her orgasm. I took it all in and then placed my lips together with hers, feeding her some of her cum. She accepted it and after a minute or two I went back to seducing Pamela. She was admonishing me, but without success. I just kept on seducing her. Without too much encouragement Pamela had her second orgasm, which I also took orally and again I shared it with her. Her first two orgasms had come too easily and I decided she was good for a third one. Pamela was still admonishing me, but not really objecting to my actions. I kept working my hands and the fur over all the sensuous parts of her body. She finally started getting wet again, at which point I rubbed my penis against her clitoris, getting it nice and wet. As her body again began to tremble, I started to gently insert my penis. Slowly at first, moving in and out, going deeper each time. Suddenly she lifted her hips and we started moving together. By this time I had a good sense of timing and Pamela’s preferences, so I easily fell into her rhythm. We both had our orgasms together, after which I noticed a smile of satisfaction on her face. This normally meant that she was satisfied, but this was the time for which I was waiting.
I immediately entered Pamela again and started stroking. Pamela immediately resisted and demanded that I stop. I just continued. She was still resisting and demanding I stop. My response was, “Yes, you want me to keep going.” She responded, “No, I want you to stop.” I just continued to stroke, in and out, deeper and deeper. Suddenly I saw a gleam in Pamela’s eyes. I had seen it before, and it meant bad news for me. The only thought that came into my mind was that she realized I was going to have my orgasm before her. Somehow Pamela realized this and took the initiative. She was going to make me have my orgasm before hers and then she would be back in charge. I summoned all of my mental ability and strength to hold back my orgasm and was succeeding. It was agony trying to hold it back, but I was doing it.
Then, I noticed another change in Pamela’s face and eyes. I also noticed a change in her movement. She was now going to try to have an orgasm. She began to encourage me to hold mine back and was also struggling to have her own. Signs of both pleasure and pain were evident in her face. It seemed to me that Pamela now wanted to have her orgasm to please me. In turn, it became very important to me to hold my self back. I was not going to disappoint her by reaching an early climax. I was going to hold it back until she was ready, so we could have our orgasms together. I could feel the strain she was putting herself through as she was trying to have her fourth orgasm. Simultaneously, I painfully struggled to hold my orgasm back and also encourage Pamela. My desire became one of pleasing Pamela, rather than satisfying myself. She was trying to do the same for me. Our desires were such that we were encouraging each other with both painful and joyful screaming. Finally Pamela exploded with her fourth orgasm with extreme intensity. With the feeling of her having hers, I relaxed and let my love nectar freely flow into her with an orgasm of equal intensity. The sounds of encouragement and pain became sounds of satisfaction and pleasure. Then both of us looked at each other with fulfillment, and with exhaustion. Pamela just collapsed onto her back and as I became flaccid and withdrew from her, I came up alongside her and took her into my arms. She willing came into my arms, her exhaustion evident, as I pulled the fur spread over us and we relaxed in each others arms.
It was late morning when we finally got out of bed. We decided to just go down for a swim and then relaxed for the remainder of the afternoon. For the first time since I arrived, I felt more than a physical attraction toward Pamela. The affair that we had earlier that day seemed to be a turning point. Over the next few weeks things began to gradually change. Pamela did not ease up on her discipline. I still had to dress in furs, do my makeup and go window shopping in town, but when I made a mistake, Pamela offered helpful hints to correct my mistakes. I was also beginning to select the furs and makeup that we would use that day. I was also starting to accept and enjoy the clothes, mainly because they were fur and the softness of them made me feel good. I still had mixed feelings about the makeup, but I willingly accepted it since Pamela seemed to be pleased. We went out to town more often. I became comfortable with my appearance in public. We frequented several restaurants for meals and did a great deal of window shopping at many of the shops in town. My favorite places were the furriers, where we would try on various furs. The sex in our relationship was also improving. We were more eager to please each other and were getting more emotional in our relationship. Kissing, petting and conversations, with and without words, were becoming more sensual and satisfying.
One night, about two weeks later, I saw that Pamela was extremely restless in bed. She kept tossing and turning unable to sleep. She rebuffed me when I asked what was wrong or if I could help. She just told me to go to sleep. Finally, she got up, went over to and sat in a chair by the window. I pretended to be asleep, but just made enough noise to tell her that I was also awake. After a time she got up and came back to bed. As she was coming across the room, I heard her mutter to herself, “What the fuck. I’m going to do it.” I was surprised because of Pamela’s insistence on the use of proper language. She felt the use of some language reduced the pleasure of sex, since it had a nasty connotation. However, she made it back to bed, gave me a kiss on the cheek and after I put my arms around her, she went to sleep with her head against mine.
The next day, as we were getting dressed, Pamela gave me a pair of panties to wear. Looking at it, I noticed it had an overlapping slit in the front with a clasp to keep it closed. It was the same type as she had always worn. It was just one of those things I did not notice until now. I asked Pamela if there was any reason or significance to this change, she avoided answering by remaining silent. There must be some significance, but she was not telling me. I did not give any further thought to this change. Other than this isolated incident, things were going along nicely for the next couple of weeks.
One evening, when we were having dinner in town, Pamela brought up a question I had been avoiding. What was I going to do when I returned home in about two weeks? I knew that I would have to stop wearing makeup and woman’s clothes and again wear my own. Over the next week I struggled with these questions. Pamela and I discussed them openly and she carefully made sure that all of the options were thoroughly discussed, but she carefully avoided making any suggestions about what I should do. I also tried wearing my regular clothes. My pants irritated my skin and my shoes felt loose. After careful thought, I decided I would remain cleanly shaved, except for the heart. This would leave my skin somewhat softer than normal. I would continue to wearing stockings and panties. I could always put a pair of socks over them so they would not be visible in public. This meant I would also wear a garter belt so the stockings would remain tight and the seams would be straight and properly centered on the back of the leg. The panties would be no big deal since I normally did not wear underwear, although they would not be fur. Not being able to have access to the furs was going to be difficult for me. I had become completely comfortable wearing them and did not want to give them up. The makeup would go, except that I would use clear nail polish on my nails and perhaps a clear lip sealer on my lips. I would have to think about this.
The next week Pamela took me shopping and bought me what seemed to be endless gifts. These included panties, garter belts, other lingerie and stockings in various colors. She came up with a good idea for shoes. She bought me two pair of cowboy boots. One pair was plain brown leather for everyday wear and the second pair was a bluish green lizard skin for dress occasions. Both pair had block heels and the top of the boots came up above my ankles. The top of the boots would always be covered by my pants so I would not have to wear the extra pair of socks. Since all of her shoes had pointed toes, my toes were now closer together which was making my own shoes feel loose. I had no problem adjusting to the heels and pointed toes of the boots and they did make my feet feel more comfortable. Pamela also made it impossible for me to thank her, although I tried using everything she had taught me over the summer.
A couple of days before I was to leave to go back home, Pamela started getting me back to looking like a boy. She cut and colored my hair so it was close to my natural color, cut and reshaped my nails so they looked masculine. I was reintroduced to my clothes, which I had now forgotten about. The afternoon before I was to leave, we put out my clothes for the next day and packed everything else. Pamela again surprised me, by putting six pair of fur panties in with my other things. She told me they were for those special occasions I was going to have when I got back home. We stayed home that evening and I again tried my best to thank Pamela.
The next morning she drove me to the airport for my flight. We did our final good byes in the car since we both knew they would be very emotional. We walked to the departure gate together and I boarded my flight home. I had just spent the summer having the best time I have ever had. I had sex in every way possible, satisfying Pamela at her every whim. She taught me more about sexual relationships than I ever thought existed. We did many things together and this summer will always be memorable to me. More things than I can ever relate. Pamela was one really classy and kinky lady. Needless to say, I didn’t masturbate at all, I could barely keep up with her demanding body. I was really sad when it came time to leave. In many ways I had really become hers.
When I got home, my mother told me that she received a nice letter from Pamela, saying that she thought that she had cured me of my problems. Mom said that she hoped that Pamela hadn’t been too hard on me. I just smiled and said, “Oh, no, it wasn’t that bad after all, Mom.”