I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have children, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the kids came', 'we are too tired because of the kids', and the best of all 'we fight too much over money and the kids'. I would just listen and laugh in my head at them. Then I met Emily. Emily was just your average sized woman on the outside, size 12 full figured, but she carried it well. It was her big boned body frame rather than just added weight. She had beautiful soft red hair that cascaded over her milky white skin. She had just enough freckles on her face to be attractive and not over powering. Her eyes were emerald green. Her breasts are the softest I have ever felt, white with the pinkest nipples that stick out a half inch when aroused. My heart would skip a beat when she laughed. I was hooked. I finally realized what my friends felt when they decided they found a woman that changed their life.



At my age I gave up on having children of my own, with Emily came and instant family. Emily has a twenty-two year old daughter that is smoking hot. She lives at home and finishing her last year of college. Emily had Jessica when she was just twenty. Jessica has her father's features, tall, thin, brown hair with obvious natural red highlights, small petite breasts, and she is very athletic. When I moved in Jessica turned into an iceberg. Her father passed away in some traffic accident when Jessica was a small child so it's not like her parents will ever get back together. I never had children so I was not looking to be this person of authority, besides the fact that she is an adult.



I work fifty percent out of my home and the other fifty percent I travel for my company. I moved into Emily's home because it was much bigger than my two bedroom condo, which I rent now. Emily has a large four bedroom home, pool, private large lot. She used the money from her husband's life insurance to invest in a home which is now bought and paid for. She was one smart woman.



Emily is an emergency room physician so she is at the hospital often and on call every other weekend. Our schedules allow for a lot of freedom, but it also means that we do not cross paths on a daily basis. We have to schedule sex in order to have it as regularly as possible.



Jessica does work hard at school and homework. The ice princess does have good study habits and good grades. She will go for her MBA and/or Phd in clinical psychology.



I asked Jessica why she was so hard on me and her response was that she didn't want to get too close in case it didn't work out with her mother. She said that men didn't stay too long because of her mom's work schedule. At least it wasn't me personally that she hated, she just doesn't want her feelings hurt. I could appreciate that.



I was working in my office at home, bored. What else do you do when you're bored? Surf porn. I started to surf porn and went to a few BDSM sites. I find dominant women to be very sexy. Some of the sites had men tied up and others had them dressed in women's clothes. I found some of the men looked pretty good wearing nylons and panties. I was almost hairless and still had a flat stomach so I figured I would look pretty good in some sexy clothes. I was alone at home so I thought I would play a little. I went to our bedroom and started to open the drawers pulling out some panties and bras. The panties were too big. Emily was a size 12 and I was thinner with a 30 inch waist, so they didn't look good. I was 5'10" tall, one hundred and sixty pounds. The bra barely stayed up on me. I was getting frustrated.



I started to walk around the house and found myself going into Jessica's room. Jessica's room was in perfect order. I opened her nightstand drawer, condoms, vibrator, lube, and nipple clamps, very naughty girl. I was careful not to touch or move anything. I moved to her dresser and opened the top drawer. Eureka, panties, bras, slips, and nighties. It was a veritable silk and lace bonanza.



I was standing in my step-daughter's room naked, running my hands through her silky lingerie. I felt so naughty and horny. My cock was hard as a rock. I reached down and gave it a couple of strokes. Crap that felt good. I was now super horny. I had to try on some clothes. I pulled a pink pair of panties out, with red bow ties on the sides. I bent over and slipped my left foot through the opening, and then the right. I slowly pulled them over my calves and up my thighs. I took a deep breath as the silk glided up my legs. My body shuddered as I pulled the panties over my hard cock.



I had to have more. I searched her drawers and pulled out a black slip. I pulled it over my head and let it cascade down my body. I ran my hands up and down my sides feeling the cool soft feel of the silk. I walked over to the closet door mirror to look at myself. The slip rubbed against my nipples and made them stick out. I was getting so excited.



I couldn't take it anymore, I threw myself on Jessica's bed, pulled out my hard cock, and started to jackoff. I was rubbing my nipple through the slip and pretending I was a girl, "Oh you like your tits played with don't you slut? You look so sexy in your slutty panties." I was wiggling my ass in the panties and dripping precum like crazy.



"WHAT THE HELL ARE YOU DOING?" Jessica was standing in her doorway screaming at me.



I heard the volume of the scream more than I heard the words. I knew I was busted and a million thoughts ran through my head as my cock shriveled down and popped back in the confines of the silky panties. "OH SHIT!" I rolled off the bed, away from the doorway, in a feeble attempt to hide behind the side of the bed.



"OH SHIT! IS RIGHT! What are you doing in my room James? Or do I need to call you Jamie now, you sick perverted fuck? My mother is going to kick your ass out of this house so fast. I knew not to trust you." Jessica's face was beet red.



"Please Jessica don't tell Emily. This was the first and only time this happened, I swear." I was pleading my best case standing in a slip and panties. I stood up, without thinking, and walked towards Jessica as I apologized.



Jessica stared me down, fire burned through her eyes, "Get out of my things. NO wait; keep them I never want to see them again. Look at you all dressed like a little sissy. Is that why you're with my mother, so she can dominate your sorry ass? I find it pathetic that a man can be so submissive."



I was now standing in front of her begging for the slightest bit of sympathy and praying that I can convince her not tell Emily. "Please Jessica I'll do anything you want just to keep this between the two of us. Please don't tell Emily, it will destroy her knowing about this. Please, please." I even sounded pathetic to myself but at the same time I was getting aroused at being in silky panties and being scolded by a woman. I felt my cock growing against the panties. When I moved my nipples were super charged as they rubbed against the satin slip.



My growing cock didn't go unnoticed, "Oh my god, you're getting a hardon from me yelling at you. You are one sick fucker."



Jessica crossed her arms and held her stance, "If my mother wasn't so damn happy with you I would call her right now. I do not know what she sees in you that she would want to stay with you. I will be damned if I am going to be the one that breaks her heart. I need some time to think about this."



Jessica turned and stormed out of her room, leaving me standing there in panties and a slip. I went to go after her, but I heard the front door slam and knew I was through. I ran to my room and pulled off the panties and kicked them aside. I went to take off the slip and as I moved the long flowing slip softly gliding over my bare ass and cock I was getting hard again. I was mad at myself for enjoying the feel of the silk against my naked skin. I kept the slip on as I went and gathered my man clothes. The feeling of walking around was turning me on more.



"Ah, fuck it!" I said to myself. "My life is over anyway" so I grabbed my hard cock through the slip and began to beat my cock with one hand and started to tweak my nipple with the other. The silky sensation pushed me over the edge and I was shooting my cum through the slip. The slip kept my cum from shooting out so my cum just oozed through the silky material. I wasn't prepared to catch my cum so on impulse I brought the puddle of cum up to my face and sucked it off the slip. I was so turned on that even when my lips made contact with the soft fabric by cock twitched. I swallowed my entire load down. I actually enjoyed the thick milky substance. I closed my eyes and swirled the concoction around in my mouth. It was smooth and thick. I thought it would be hotter than it was. I was expecting a sharp bitter taste, rather it was smooth going down my throat, with a hint of bitter and tang together. It wasn't unpleasant at all.



I pulled off the slip and made sure I had sucked all of the cum from it. I grabbed the panties as well and tossed them into the hamper. I reluctantly pulled on my 'man' clothes and returned to my home office to think. The hours felt like days as I waited for Jessica to return and find out my fate.



Four long hours went by. It wasn't until five thirty before I finally heard the front door open and then close. I assumed Jessica was going to tell me to pack my things and be gone before Emily got home. I was shocked and scared shitless when in runs Emily. I thought her haste was to chew me a new asshole and kick me out, until she rushed past me, gave me a peck on the cheek, and continued to our bedroom.



"I gotta go back to the hospital. I just received a call when I was pulling up to the driveway, big building on fire and we are going to get hit hard. I'll probably be there all night." Emily grabbed some clean clothes, changed, and was out the door in five minutes. It was obvious that she hadn't spoken with Jessica.



Another three hours passed and it was almost nine o'clock. I hadn't eaten dinner, my appetite was gone, and so I called it a night. I jumped in the shower before getting ready for bed. I let the hot water roll off my back as the tension floated down the drain with the water. My body is pretty hairless except for the usual head, pits, crotch, and ass. I have never had hairy legs side from a little patch along my shins. Having blonde hair and light skin, even the pit hair seemed sparse.



I was still horny from walking around wearing silky clothes so I grabbed Emily's shaver, poured some liquid soap in my hand, bent over, and began to lather and shave my legs. Once I felt how soft my skin felt I couldn't stop myself. Before I knew it I had my arm pits shaved, my cock and balls were now hairless, and even the hair in the crack of my ass was now void from my body. Even the water felt different. My cock was rock solid and I couldn't wait to put on a slip or nighty and go to bed.



I shut the water off and dried myself off with a towel. My skin was on sensory overload. Anything and everything that touched me right now brought me that much closer to cumming. Emily's granny panties were not going to do it for me. I didn't dare go back into Jessica's room and the slip and panties have dried cum stains on them. I fished around Emily's drawers until I found lodged way in the back of her drawer a matching red baby doll top and panty set. I pulled it out and held it up to my body.



The top was sheer red with a red satin ribbon outlining the entire top. It was open in the front like a short robe, a red silk thin belt with two red fluffy balls at the ends, and matching red sheer panties that were also outlined with red silk. They looked smaller than her usual things, this must have been a gift that she has had tucked away for long time.



I put my arms through the top and pulled it on, leaving it untied. I bent over and pulled on the panties. My shaved body was on fire. I looked hot in this outfit. I stood in front of the mirror and spun around. The top floated away from my body and as I stopped it fell lightly back against my body. My cock was bending in the confines of the panties.



Then I heard the front door slam. I began to panic. How would I explain my shaved body to Emily? I need to change and put her things away. She will be up the stairs and in our room in no time. Then I heard Jessica calling "James, are you home?"



I was still in panic mode as I threw the top back in the drawer and as I heard Jessica coming up the stairs I grabbed a pair of sweat pants and a t-shirt and slipped them on over my red panties, just in time to hear her knocking at the bedroom door.



"James, are you in hear?" Jessica called as she softly knocked on the bedroom door.



I was sitting on the edge of the bed, my heart was racing. In a low solemn tone I managed to say "Yes Jessica, I'm still here."



The door opened slowly and I sat awaiting my fate. Jessica walked in carrying a small pink bag. "I want to apologize for yelling at you this afternoon. I had every right to yell for being in my room and violating my things, but for someone that is working on a degree in psychology I didn't stop to recognize what you were doing and I just attacked you."



Was I dreaming? I thought this bitch of a girl was going to rip me to shreds and now she was apologizing to me? I don't get it. I sat there with my mouth open. "I am so sorry Jessica. I should have never gone in your room or touched your things. I was caught up in the moment and I wasn't thinking either."



Jessica walked over to me and gave me a hug. That was the first hug she has ever given me, let alone any ounce of sincerity. "I spent some time in the library and found that men wanting to wear women's clothes are more common then I realized. But if you have latent homosexual feelings I want you to be honest with my mother before she gets hurt."



I jumped off the bed, "Whoa! NO I don't have latent homosexual feelings. I just liked the feeling of the material against my body. I love your mother and LOVE having sex with her. I got caught up in the moment because I was surfing porn and was sexually frustrated, that's all."



"Surfing porn is very common as well, for both sexes. So you're just getting in touch with your feminine side, is that it? Tired of being the macho man and wanting to feel less pressure to please, you want to be pleased, pampered, feel special, like you treat mom? I understand mom works long hours and doesn't have time for you or me, I get that. You're not looking for a man to treat you like a lady? You just want to be put on a pedal stool for once, shown some real effection?"



I looked down at my hands, "I guess, something like that."



Jessica continued to taunt the truth out of me without me even realizing it, "Putting on women's clothes makes you feel sexy, attractive, desirable, don't they?"



My eyes were glazed over she nailed me, "Yes. They make me feel sexy."



Jessica handed me the bag, "Here I went out shopping and bought you a little apology gift. Go on, open it."



I opened the bag, reached my hand in, and pulled out a tissue wrapped bundle. I could tell it was clothing of some sort. I looked up at Jessica. She was staring at me with anticipation. I slowly removed the tissue paper to uncover soft silky pink garments. My first thought was that Jessica was making fun of me.



Jessica grabbed my hand before I could object, "Look James, I want to be friends. This will be our little secret. After thinking about things I realized that it would be better that you express yourself here at home than elsewhere. If you promise to keep your dressing up to this house then I will support you 100% and let you walk around in any outfit you like. I won't tell mom unless you want me to or when you want to. But if you're going to dress in pretty clothes than I want you to have your own and not wear my things, deal?"



My mouth was gaping open. Did I dare trust her? Was she really being sincere? Would I enjoy the feeling of silk against my body if the taboo was taken away? "I'm not sure Jessica. I did it once because I was horny and lonely. I'm not so sure I want to pursue this anymore. I appreciate you wanting to help me. I don't know if I would be comfortable walking around in lingerie with you here."



Jessica grabbed one of the items in my hand and rubbed it against my face, "Tell me this doesn't feel real nice against your skin Jamie? I have a nice pink slip, pink silk panties, and pink nylons with garter belts. You will look so sexy in this outfit and you can put them in my closet when mom is home. Let it go Jamie do what makes you feel good. Besides, I think you'll look sexy in this outfit that's why I picked it out with you in mind."



Jessica continued to rub the silky slip all over my face and arms. I closed my eyes and felt my cock getting hard. I soft moan escaped my lips giving me away to my desires. "That's it baby feel the soft material against your skin. Wait until you feel the nylons being pulled up your legs. Don't deny yourself Jamie."



I was ready to shoot my load when I opened my eyes and I could see the same lust that I was feeling reflected in Jessica's eyes. She was getting off on me dressing up. I grabbed the package and went into the bathroom to try it all on.



I raised my arms and let the slip slide down over my body. The cool material against my freshly shaven body was pure bliss. I then sat on the edge of the bathtub and started to put on one of the nylons. I wasn't sure how the garter belt would work so I grabbed the pink silk panties and pulled them up and over my hard cock. The head of my cock was sticking out the top of the panties. A clear drop of precum was leaking out already. I used my finger to clean the drop of precum, brought it up to my mouth and rubbed it on my lips like lipstick. I ran my tongue over my lips feeling the smooth feel of my cum on my lips.



I stepped out of the bathroom holding the nylons and garter belt, "Um Jessica I'm not sure how these work."



Jessica jumped off the bed and came to my assistance, "You look nice Jamie. First let's have you lip the garter belt on." Jessica held the belt open at my feet waiting for me to step inside the circle.



I pointed my toe and stepped into the circle one foot at a time. Jessica slowly pulled up the garter belt, "Jamie your legs are sooooo smooth. You're going to love the feeling of nylon against them."



When she got up to my crotch she pulled on the garter belt to stretch it over my hard cock. "Looks like someone is enjoying this?"



Jessica instructed me to sit on the edge of the bed as she rolled and bunched one of the nylons down in her hand. She told me to point my toe as she slipped it on my foot. She pulled up the nylon over my heel and up my calf. I could feel my eyes roll back in my head as I threw my head back. "Feels good, huh Jamie? Your skin is so soft. You really do have feminine features. I find that really sexy."



Jessica ran her hands up and down my nylon covered leg before she repeated her efforts on my other leg. They nylon against my smooth skin was causing my cock to leak forming a big wet spot on my new panties. I could feel Jessica's hands running along my legs. She attached the nylon tops to the garter clips that dangled from the belt.



Jessica stood up and took a step back, "Simply lovely Jamie," is all she said that caused my face to flush.



Jessica quickly grabbed my hand and pulled me into the bathroom. Jessica stood behind me and turned me to face the full length mirror. "Look at how nice you look in your pretty outfit. Does this make you feel sexy?"



As Jessica asked me how I looked she was running her hands up and down the silky slip. This was the attention I was craving. I wanted to be the center of someone's affection, to be wanted.

