How Nathan became Natalie Ch. 04

The school year ended and Kevin graduated and Jenifer and I went home for the summer break and we got part time jobs for the summer. Jennifer got a job working with her father's very large and lucrative construction company as a marketing representative; which was her major in college. It was a great experience for her but due to the fact her father's construction firm was so large she did travel often. I got a job working part time in a call center for a television cable and internet provider company. My job was a nine to five job and no weekend work and rather easy and often boring.

A week after I got home from school my parents and I had a huge falling out, the details are not important but it was such a falling out that I moved from their house and had little contact with them even to this day. I could not afford my own apartment since I worked only part time so I lived with my older sister and her husband for a few days but that did not work out well either and the living situation was very tense. My brother-in-law never liked me and I heard him and my sister argue often about me living there and him saying several times, "I want that sissy, faggot out of my house."

Not wanting to cause any problems with their otherwise perfect marriage I decided to move out and called James. James was one of my mother and father's closest friends and I had known him for years. James lived about fifteen miles from the town I grew up in and he had always been close to me and my sister. He was divorced for about twelve years now, never had kids and never remarried, but dated occasionally but never anything lasting. When my mother asked why he does not find a nice lady and settle down again, James would laugh and tell her he tried that once and it did not work out. He was very open to me living with him for the summer and said it would be nice to have someone around the house to look after things when he went out of town for his job.

James lived in a nice three bedroom; two bathroom home that was built in the 1850's and considered a historical home. He brought the home years ago when it was in a state of disarray and spent many years remodeling it to its former glory. It also had a one bedroom guest house in the back that he had remodeled also and it had its own kitchen and bathroom and a small living area. He always said he wanted to rent it out for some extra income but never did. It was perfect for both of us. I had my own private living area and when James went out of town on business I could look after the main house.

I would pay rent, naturally and be responsible for the extra cable costs for the television, but the other utilities he would provide and of course I was responsible for my own groceries. The small guest cottage came furnished so I did not have to worry about that or buying a new bed. Due to the low rent he charged me I also did the yard work such as cut the grass and trim the hedges. Overall it was perfect for me.

Jennifer came over a few times, we still had not had sex yet but she continued to give me oral sex and now I was going down on her pussy, her suggestion not mine. I was surprised when I saw her pussy was hairless except for a small patch of hair over her sex and she laughed and told me once she saw I had shaved my private area she wanted to try as well and she liked it that way.

I enjoyed going down on her a great deal. I loved the way her hairless pussy looked, how wet it got when she was aroused, and the smell and taste of her. Naturally I did not know what I was doing the first several times and after a while even with her verbal instruction of where to put my mouth and how to use my tongue and fingers, she would stop me and have me watch as she masturbated to get herself off. Sucking cock was so much easier. After a while I was able to give her an orgasm with my mouth but most of the time she would kindly tell me to stop and she would finish herself as I watched. We did not spend a great deal of time together over the summer, with her job and the traveling.

I did miss Kevin a great deal. I missed the sex with him but what I missed the most was how he treated me like a girl and how I could dress up for him as a girl and be all feminine for him. I did practice my makeup by watching you tube tutorials and why not yet an expert by the time the school year ended I could apply my makeup decently. I tried to contact Kevin just to keep in touch but he never replied back to my text messages or emails. When James was out of town on business I did enjoy dressing up as Natalie around my apartment. I had purchased more panties, some lingerie, and even a few female outfits. I would dress up as Natalie, prance around my place, and pretend I was a girl as I cleaned, cooked, or just sat alone watching television.

I also did miss the sex and having a nice penis in my mouth and ass, I had to admit to myself. My desire to dress as a girl and be treated and fucked like one soon got the better of me and I did something I thought I would never do. I posted an ad on an adult hookup site online, took some pics of me dressed as Natalie in various poses and lingerie and panties and bra and posted them (blocking out the face) on the profile. I then filled out the boxes of the things I enjoyed sexually, giving oral, receiving oral, receiving anal, and clicked a lot of "No" answers to the more kinky stuff. Basically I was looking for a masculine male who I could have a no strings attached but safe relationship with someone within 50 miles of me who wanted to meet on a semi regular basis; was not looking for one time hook ups.

After getting lots replies and sorting out the fakes, the guys who lived to far away, married men, and the freaks; I found one man who peaked my interest and by his photo he was nice looking. Fred and I exchanged a few emails and even talked on the phone, he was pleasantly surprised I had a feminine voice, and we agreed to meet in public. I told him I would not be dressed as a girl; even though Kevin told me often I could pass in public as a girl I still was not ready for that. I did however put on a little eye liner and mascara; I had that emo look going for me anyway and I had seen many emo and Goth boys wear eye liner and mascara.

Fred and I met at a coffee shop one early evening during the week. The pictures he sent me via the website must have been ones of him when he was younger, but overall he was not bad looking; besides I was not too concerned about looks. As long as the man was average looking and clean was all I was asking for. He said he was 32 but looked a little older but that was fine. He complemented me on my looks, telling me since I hid my face on my pics he was surprised to see I was so girly and pretty looking. He complimented me on my thin feminine figure and the photos I posted. I was flattered but honestly used to people telling me I was pretty like a girl. After a while he suggested we go to a motel.

I told him I did not have any of my female clothes or makeup with me but he said he did not care and I gave in. I followed Fred to a cheap motel not too far from the coffee shop and he got a room. I was excited and aroused even if I was not going to be able to dress up for him; at least I would be able to act like a girl and I was wearing a pair of panties under my jeans. Our encounter was not what I was hoping for.

When we got into the room I went to kiss Fred but he pushed me away and told me to get on my knees and suck his cock. As I got down on my knees in front of him he pulled down his pants and I started to give him a blow job. I enjoyed it of course and after a while he told me to stop and take off my clothes and get on the bed on my hands and knees. I did as he told me and Fred put on a condom and lubricated his erect penis and fucked me from behind. It felt great to have a guy fucking me again I admit and just as I started to get into it he orgasmed, removed his cock from my ass, removed the condom, got dressed, and left. I actually cried a little at the way he treated me, got dressed, and went home unfulfilled and disappointed and feeling like a cheap hooker.

I tried the dating website two more times and basically got the same result. I dressed for them; they got off quickly and left. I gave up and just satisfied my desire to be Natalie by dressing up at home alone when I got off work and masturbating while I fantasied about being a girl for some handsome masculine man and even at times I fantasized about being Natalie for Jennifer and having her fuck me with a strap on dildo; a fantasy I knew would never come true.

James basically left me alone and respected my privacy so when I was alone at home I got to dress as Natalie, which I did almost every day when I got home from work. I enjoyed it a great deal. Even just hanging out alone cooking my dinner or watching TV I would dress as Natalie and pretend I was a girl. It was so much fun and excited me a great deal.

In late June a hurricane hit Florida and Jennifer was sent by her father to the state to help with his Florida branch to help with estimates and negotiate with insurance adjustors to help in the rebuilding of people's homes and business. I was sad she was going to be gone most of the summer, but we agreed to Skype as much as we could; which turned out not to be as often as I wished since she was kept very busy and working at least twelve hour days.

I got home from work on a Thursday and was looking forward to the three day weekend for July 4th. I did not have any plans but just being off for three days would be nice. When I pulled into the drive way and drove past the main house I noticed James was home and there was a strange car in the driveway as well. Not thinking anything about it I drove to the back and parked in front of the guest house where I lived. As I was getting out of my car, James came out the back door of his house and "flagged me down".

"Hey, Nate, my friend Steve is in town and he brought over a lot of fresh shrimp and we are going to do a low county boil if you want to join us for dinner."

I grinned and told him that would be great since I was getting lonely without Jennifer to talk to. I had no friends. At my work I was classified as the gay man and the other men that worked there did not include me in the invites to after work drinks or after work socializing. To the girls that worked there I was just "darling" and they would talk to me like I was their gay best friend.

"Sure, I would like that." I told James.

I did not even bother going into my place and followed James into the house through the back door that led into the kitchen. He introduced me to his friend Steve, who was cutting up potatoes for the low country boil. In the sink was a huge pile of fresh shrimp already shelled and deveined and on the counter was some sausage and corn. As soon as I entered that house my summer changed and it changed for the better.

After the introductions James put his arm around me in an affectionate but nonsexual way. "Nate, I got you a present. It's in my bedroom." He told me.

James led me into his bedroom, his arm still around me, and when we entered his room he turned the light on and I looked around. I didn't see any present.

"On the bed." James told me in a kind voice.

I then looked on the bed and my heart skipped a beat, several beats. On the bed was some clothes but they were female clothes. It was an outfit laid out to perfection. Started with the top which was a white, silk button up blouse and on the collar was a black silk ribbon bow. Then came the skirt which was a red and black mini skirt with lots of pleats and it flared out at the hem and around the waist of the skirt was a wide black shiny faux leather belt. Beneath the skirt was a pair of long solid white socks with black bows on at the top. On the floor was a pair of patent leather Mary Jane shoes. It was a darling outfit I had to admit.

"I...I don't see anything." I told him nervously trying to act calm.

"Come sit down, Nate. We are going to talk." James told me and led me to the bed.

I was too stunned to resist. So far he had not said much but I had the feeling he knew I was cross dressing. Maybe he saw me one night through the window even though I thought I had been very careful.

I sat on the bed and James sat next to me and put his hand on my knee. "I know you crossdress, Nate." Yep I was busted. "I saw you a few times."

I felt tears form in my eyes and I got scared. My parents and I were in a very strained relationship right now and if James told my dad I liked to dress up and pretend I was a girl neither of my parents would speak to me again and more importantly they would call Jennifer's parents and she would never speak to me again. I sniffled and started to cry, yeah I was such a sissy.

"I...please, James...please don't tell my mom and dad." I did not deny it. Why should I? He had told me he had seen me.

James pulled me close to him, "I am not going to tell your parents, Nate. We all have our secrets. I have one of my own. I just thought you should know its ok if you want to dress and pretend like you are a girl. I always figured you were gay anyway and was shocked when I met Jennifer years ago and everyone told me she was your girlfriend. I mean I could not understand how a girl that beautiful was attracted to a sissy boy like you...and I did not mean that as an insult...the sissy boy part."

"You...you won't tell?" I asked and sniffled and wiped my eyes.

"Not anyone. I promise. That's why I brought you the outfit. For you to wear tonight; if you want. I want you to be who you want to be and not be ashamed of it."

Then it hit me. I was going to be black mailed into at least sucking his cock. I moved away a little, "James...I...I can't do what you want me to." I told him.

James laughed, "Nate I am not going to black mail you for sex. Let me explain something to you and let you in on my secret and Steve's." He told me and I relaxed and he put his arm around me again and shared his secret with me.

James met Steve about three years ago in an online chatroom that catered to straight, masculine men who enjoyed feminine crossdressers sexually. James had a fetish for such type of men for years. He and Steve started chatting; discussing their similar interests, noticed they live reassembly close to one another, and became friends. They even sometimes met a crossdresser online and shared her or met two and "double dated." Steve told me that a he happened to see my ad on the adult site and was unsure if it was me but suspected maybe it was; then he saw me dressing as Natalie a few times when I was not as careful as I thought.

"So I decided to invite you for dinner with me and Steve and bought you this outfit to wear. I have to also confess I knew your size because I did go into the guest house one day when you were at work and saw your other clothes and shoes and got your size off of them."

"I...what...you said you were not going to blackmail me? So...so what do you want?" I asked still very nervous and scared of what he may want of me.

"All I would like you to do, me and Steve, is for you to be yourself. Put this outfit on and be a girl like you want to be tonight. We are not asking for sex in anyway. We just enjoy the company of a pretty, sexy girl like you. We won't do anything you are uncomfortable with. Just makes two old men feel good having a girl like you around us."

I looked at James and smiled. The thought did excite me. I could be Natalie and be all feminine and girly. "I...I don't have to do anything sexual?"

"Not unless you want to."

I looked at the outfit next to me, "It is a super cute outfit." I giggled. "Ok...but can I go take a shower and do my hair first? I am not that great with makeup but I can put on some...lipstick, and mascara, and some blush."

"Yes you can, but you don't need makeup, Nate. You are pretty even now."

I smiled at the compliment and leaned in and kissed James's cheek. "Thank you and thank you for the outfit." I smiled at him, "I like to be called Natalie when I dress up."

James chuckled, "Ok, Natalie. We got a couple of hours before dinner so take your time."

I gathered up the outfit and shoes and looked over my shoulder as I walked to the door. "Whose idea was the school girl outfit?" I asked.

James smiled, "Mine. Yes I know its cliché but I liked it."

"Me too. I don't have a school girl outfit and was going to buy one." I giggled and quickly walked out of the room and to the guest house to change.

I showered and cleaned myself completely. I did not need to shave anywhere since I still used the hair removal cream on myself and shaved my private area; I had just gotten used to it and felt odd if I did not. I was not planning on having sex with either James or Steve, I mean they were both in their 40's but I cleaned my butt anyway. I blow dried my hair, styled it in a feminine style and then I went to work on my makeup. I still had not perfected the eye shadow part or the base makeup but I did use mascara on my lashes, put on my favorite pink lipstick, and applied some blush on my cheeks. I looked pretty. I painted both my finger nails and toe nails a soft pink shade.

I put on the outfit James gave me and the blouse came down just below my stomach, the skirt was a mini skirt and a nice sexy short length without showing to much unless I bent over. I had put on a pair of white satin panties I had, they were bikini cute and I thought they would go with the school girl look, and I put on a lacey white bra under the blouse. Even though I had no breasts that needed support I liked wearing a bra. The socks came up over my knees to my thighs but were not as long as my thigh high stockings so you could see some of my bare legs between the socks and the hem of my skirt. I put red butterfly barrettes in my hair; I had a thing for my hair barrettes, and looked at myself in the mirror one more time. I looked great! I looked like a very pretty girl and the outfit was sexy.

I walked back to the main house and saw James and Steve on the back deck already cooking the dinner in a large pot over a gas burner. I gave them both a shy smile as I walked onto the deck hoping they were pleased with the way I looked.

"Wow, Natalie. You look fantastic." Steve said and James agreed. I was pleased they thought so.

James offered me a beer which I declined; I did not like beer and was not much of a drinker anyway, so he got me a soft drink in a glass with ice. I was nervous but excited; not sexually excited...well a little but that was due to being Natalie more than a physical attraction to the two older men. I always got sexually excited when I dressed up like this. They both put me at ease as we talked and laughed and I giggled a lot. We talked about simple things like our jobs, they asked me about school, we told funny stories about things that we experienced in everyday life, and other topics like movies and music. I was having a great time and they were perfect gentleman and complimented me often on my looks and lady like mannerisms. I admit there were some mutual flirtations between us and a few sexual innuendoes but nothing racy or vulgar. I did like to flirt and being treated like a girl and acting like one made me flirt even more.

After dinner we sat on the sofa to watch a movie, me sitting between the two men. When we sat down the hem of my skirt rode up my legs a little but I did not bother to adjust it and enjoyed the looks both Steve and James gave my legs. The movie was some action movie with spies, car chases, and shootouts. It was an ok movie but I did not play attention to most of it. By the time we sat down to watch the movie I was very aroused.

Being treated like a girl and dressing up as one and acting like one for these two men while we talked on the deck and while we ate dinner made me feel sexy and feminine and turned me on. Then sitting between them while we watched to movie and the way they had been looking at me all night increased my arousal.