Sunday, July 17, 2011

The University Years Part 4 – Finally some dressing en femme

This is the last time I will mention Bill, after we broke up I went back to my routine of hanging out with Steve and his buddies; going on a few dates and concentrating on school.  It was very relaxed no pressure and at lot less intense.  The next bit of drama to unfold was that I needed to find a job for the summer or I was going to have to give up my apartment and move back in with my parents for the summer.  That would have been very bad because after exploring my sexuality so thoroughly during my second year of University there was no way I could go back to living with my parents and their rules.  Luckily my Gay bear angel Steve had a friend who would hire me for the summer working at his business doing office work, answering phones, filing and doing some basic accounting duties.  Luckily it paid enough to cover my rent and still let me save some money for school.  Steve also promised that in the fall I could pick up a shift or two a week at his bar to earn some extra money to help cover my expenses if I needed some extra money.  So all in all it was going to be a great summer.

One day after work I was in a bookstore checking out some novels when a gentleman started up a conversation with me.  You know basic stuff like he had read that book and thought it was excellent, or had I read any other books by that same author.  So we talk for about 10 minutes or so, and I am just about to say good-bye and he introduces himself as Mark and asks if I would like to go for a coffee and talk about books some more.  I say sure so we buy our books and head over to a coffee shop for a coffee.  I am thinking to myself well this guy certainly seems nice, and pretty smart, and it was nice of him to suggest we have a coffee so that we could continue our conversation. 

So we grab a coffee and sit down at a table and continue our conversation for about an hour.  Mark was a pretty good looking man, fiftyish, grey hair, wearing a suit and tie, clean shaven, and a nice smile.  We finished our coffee and as we standing outside of outside saying our goodbyes Mark asks if I might be interested in meeting him again tomorrow at about the same time, at the coffee shop and we could go back to his place for dinner and he would show me his collection of books.  Duh!!  Of course he was nice, he was hitting on me!  That was a first for me, getting hit on in a bookstore.  It was also the first time I had ever been hit on in a non-gay setting.  All the other times a man had made advances towards me; I had either been seduced or had been set up on a date.  I said sure and we agreed to meet up the next day after work which was a Friday night. 

So the next day we met up outside of the coffee shop and, we drove over to his place which was in a much nicer part of town than where I lived.  We went in to the house, Mark poured us a glass of wine and then he gave me a tour of his house.  It was very nice, with a great den/library that had lots of books and winged back chairs to sit and read in.  There were lots of photographs all around the house, including some nudes, which were of very high quality and I asked who the artists were he said that he was.  He said that he was a bit of a shutter bug, and when he was younger even thought about becoming a professional photographer, he even had his own darkroom in the basement.  In a lot of ways he reminded me of my first male lover Mr. P. in that he was obviously pretty well off, and had a bit of an artistic streak and dressed well.  So we hung in the kitchen while he prepared dinner, turned out that he was a lawyer, had been married in his early twenties, got divorced before he was thirty and had been single ever since.  Mark liked to travel when he had the chance and had actually just turned sixty.  I told him that he must be lying to me because he looked fifty at the most.  He gave me a little peck on the cheek and said that I was being very sweet but no he was really sixty.

When he gave me the peck on the cheek that was the first time he had touched me, I remember thinking to myself; that it was about time because I thought I might have been wrong about why I had been invited over. 


After dinner we retired to the living room with another glass of wine and continued talking.  Finally Mark brought up the topic of sex and very politely asked me if I would like to spend the night with him.  He told me that he realized that he was much older than me, but he thought that I was very attractive and wanted to fuck me.  That is what I have always liked about older men they at least tell you what they want without beating around the bush.  Lol

I told him that I loved the idea and had been hoping he would make a move all night.  So he told me to grab my wine glass and then he grabbed my hand and led me upstairs.  Once upstairs he undressed me and was delighted that I was smooth all over.  As he undressed he made a comment that he would love to fuck me while I was wearing a black garter belt and stockings because it would look great against my smooth white skin.  Well I just turned beet red because a man had never said that too me.  He looked at me and said “Are you into that?”  I sort of stammered and stuttered for a moment and then said “Wait here I will be right back.”  He left the room for a couple of minutes and then came back in with some stockings and a garter belt. 

I said “I really am not into that stuff.”  But Mark replied, “For someone who is not into this stuff you sure have a raging hard on.”  So he came over gave me a big kiss with lots of tongue and put the garter belt on me.  He then helped me on with the stocking and attached them to the garter.  I just stood there getting redder and redder.  Finally when he was done, he stood back and said I looked very beautiful.  He then led me to the bed and started making out with me.  Mark was very passionate and very tender and it was as much about me receiving pleasure as him.  I was really turned on but was feeling a little freaked out by wearing the stockings and garter belts and being with a man.  I know I had always dreamed of it happening but all I could hear was the disdain of Steve’s voice in my head making comments about Sissy faggots and not being real men for wearing lingerie.  Steve was all about masculinity although he too liked it that I was smooth all over but he claimed it was because he liked the person he was fucking to be smooth not that that they were in any way femme.

Mark reached into his bedside table and pulled out a small bottle and opened it up.  He then put it under my nose and said “Have a sniff of this it will help you relax.”  I asked what it was and he said that it was called poppers and after a couple of sniffs I would feel much more relaxed and passionate.  So I inhaled deeply a couple of times and wow did I feel horny.  I felt this how flash all over my body and a little light headed, but I could feel all of my inhibitions just melting away.   Mark then rolled me over onto my stomach lubed me up, slipped on a condom, then had me get up on all fours and started pumping.  He reached around every few minutes and told me to inhale the poppers again.  I just did as I was told and let him keep riding me until he finally exploded inside of me.  After he pulled out, he took off his condom and then went down on me and gave me an amazing blow job.  After I had blown my load Mark came up and gave me a deep French kiss, and still had some of my cum inside his mouth.  Which is a real turn on in my books, tasting your cum on someone’s else’s tongue.  Mmmmm

So after we finished and lay relaxing in bed drinking some wine I asked Mark why he had stocking and garter belts.  He laughed and said that he had a huge collection of lingerie because he liked bringing men home and having them dress up in the lingerie and then fucking them.  He said that he had lingerie in various sizes, styles and colors, plus shoes, wigs and even some dresses, skirts and blouses.  I asked him if he ever dressed up and said no, he did not dress up but he was attracted to men who did like to dress up.  He then asked me about my experiences and I explained to him that I only dressed up at home, except for the few times in high school that I went out late at night dressed driving around in a car.  I also told him that he was the first man who I had ever had sex with while wearing woman’s lingerie. 


After that we went to sleep the next morning Mark asked if I would like to go home or spend the day hanging out some more.  I said I would stay if he wanted me to.  So we grabbed a shower together and he asked if he could shave me.  I said I had shaved everywhere the previous day but he said that he wanted me silky smooth so he lathered me up and shaved me from my neck down completely; which was very erotic.  We then got out of the shower and I shaved my face while Mark towelled off and then went to get dressed.  Once I finished shaving my face I was smooth from top to bottom and ready to play.  Lol

When I got back to the bedroom Mark had a bunch of different outfits laid out for me.   I stood there stunned because everything looked gorgeous; he had great taste in lingerie and even had brought out a couple of dresses and lots of shoes for me to try on.  I asked what he wanted me to wear first, he said try to find some shoes that fit and then we will go from there.   I tried on all of the pairs of shoes and found two that fit, a pair of black pumps with 3 inch heels and a pair of red open toed pumps with similar size heels and then the dressing began.  I stayed with him all day Saturday until Sunday afternoon playing dress up.  I could not tell what got him more excited the woman’s clothing or me dressing up in them.  He certainly was the only gay man I ever met who got off on woman’s clothing.  After I had tried on some of the outfits he already had laid out for me, he took me to a small bedroom that had been converted into a closet and it was full of woman’s clothing.  He had dresses, skirts, blouses, shoes, and enough undergarments to stock a small store.  Whenever he would pull something out you could just see his eyes light up when he talked about the garment and you could see him get a hard on under his pants.  It was truly amazing.

He fucked me at least four times on Saturday and once before I left on Sunday and he gave me over a half a dozen blow jobs.  There was certainly a lot of sex and I was very tired when he took me home on Sunday afternoon.  He even gave me some lingerie, a couple of dresses and shoes to take home with me.


So Mark became my summer romance between second and third year of University and the relationship lasted about two months.  We would get together on weekends, meeting after work on Friday and then we would spend until Sunday afternoon together.  Every weekend he always surprised me with a new outfit and lots of new lingerie.  I kept telling him that was not necessary but he insisted because he wanted me to look good and have nice things.  I would dress for him all weekend long and we would have lots of sex.  Eventually he convinced me to allow him to take some photos of me some nude and some dressed up totally.  I wish I still had them because some of them were pretty good if I do say so myself, but I purged them in my mid-twenties when I was going through one of the periods when I was getting rid of all things that had to do with wearing woman’s clothing and all things gay, vowing to be a good heterosexual man, and never having sex with another man again.  Like that ever lasted for long.  Lol

Anyway, what finally broke us up was that I got bored.  Mark was a lovely man but I missed going out and doing stuff.  I hated being in the house all of the time and when I was with Mark all we ever did was stay in house so that I could be dressed up in female clothes because that is what he liked.  I liked it as well but offered to wear woman’s lingerie under my male clothes so we could at least go out; but that was not the same for Mark.    


As they say every relationship is a learning experience.  From my relationship with Mark I learned that there were men out there who liked guys who dressed in woman’s clothing and when I was dressed as a woman I could be considered sexually attractive, well at least to one guy.  I also learned that I needed more than just dressing up to make a relationship to work.  The fact that I was not comfortable going out dressed because I did not want to be found out was a problem.  But the fact that Mark only wanted me fully dressed all the time was also a problem that we could not overcome.

 





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