Pretty In Pink 6

I always remember thinking how bland men's underwear was compared to women's. In the animal kingdom, the male usually has the prettiest colors. Not so in people. I suppose traditionally, men's underwear is supposed to be functional while women's are fashionable.

I was a late maturing kid. I was probably about two years behind some of my classmates. When I did get my growth spurt, I was still small for my age. I finally grew to about 5'-7" and topped out. After maturing some, I managed to run cross country. I was not muscular, but the training was very helpful. I did not think much about lingerie during those years.

During college, I started dating a hometown girl two years younger than me. It was my first real girl friend and I was head over heels in love. She was still in high school and managed to have a few boyfriends there while dating me on the weekends. When we finally had sex, she turned out to be a virgin. I later believed that she let me pop her cherry so she could enjoy sex with her high school boyfriends as well as me.

It was a tumultuous courtship and she assured me that the guys trying to date her were just bothering her. During my senior year in college, we got married and tried to live on love. Marriage was what she said she wanted, but after a few months, living on love and little money was not to her liking. After two years we were done and she moved on to greener pastures.

I was devastated. I changed jobs and started in a new career which took virtually all of my time. After the marriage ended I was very unsure of myself and afraid to try to start a relationship. At this time masturbation was my only outlet. I did have sex with a few prostitutes, but I was totally inept at picking up women.

Eventually I met a much younger woman who had a dynamite body and a bubbly personality. I knew her for months through other people. She was very nice and outgoing. An accidental conversation among friends ended up with someone implying that we should date. In a roundabout way, she did not discourage the idea, so I asked her out for real. I really thought this was a onetime pity date. I enjoyed the company of a beautiful younger woman and assumed we would drift apart after a few dates. We ended up getting married.

Going back to the time after my divorce, the lack of sex and my inability to start a new relationship left me horny as hell. After a while, masturbation became unsatisfying. I re-discovered the love of panties. I would order from department stores and get everything delivered by mail. I ended up buying some pretty sexy panties and body suits from Fredrick's of Hollywood.

My new girlfriend, Jessica, had no idea that I had a panty stash that I wore during masturbation and occasionally out. As we continued dating, I fell in love again. This time it was with a more vibrant and self assured woman. I could not believe that I got so lucky to attract such a beautiful woman. She is 5-8, just slightly taller than me. She has the most beautiful hourglass figure I have ever seen. Her hips are slightly large but not fat. What sets her aside is that she has a twenty inch waist. Also, she carries a 34D bust. The most outstanding feature is that tiny waist flaring into her magnificent hips and ass.

As our relationship grew and we talked of getting married, I decided I had better get rid of my panties and lingerie. I reluctantly tossed all my pretty things into the trash.

Before our wedding, her friends threw her a lingerie shower. I was quite impressed with the bridal lingerie when she showed me. Our relationship was never built on sex, but sex was great after we were married. I could not make her cum with my cock, but she loved oral sex and I could make her scream and moan when I ate her pussy. The combination of her sexy body and her pretty lingerie turned me on constantly.

My work was very demanding and I traveled much of the time. I was on projects for months at a time. Some of the projects allowed me to travel home occasionally. Some did not. As I was missing so much sex and I had no desire to go out and cheat on Jessica, I resorted to masturbation between my trips home. I ended up getting a new assortment of lingerie from on line stores and eventually worked up the courage to go into retail stores and pick out my own items in person. I got some looks from the clerks, but not as much scrutiny as I had anticipated.

After this the issue became how to keep these items and not be found out. I gathered a larger collection than I could hide sometimes and when the project ended, I would throw some of the lingerie out before I returned home. As time passed and I got bolder, I started reading stories on line about crossdressers and female impersonators. I became hot to try to dress as a woman. I slowly purchased a stash of makeup, lingerie and clothing from the retail stores. I went to large resale shops and purchased some skirts, blouses and shoes. I was surprised how easy it was to find sexy high heels in good condition at these shops. As I stated, I am not a large person and my muscles are more of the long and skinny, so I fit reasonably well into feminine clothing. I really needed more ass. I tried towels in my panties, but they were too lumpy.

Eventually I ordered a shapewear girdle with padding and contouring. Then I took the real risk of getting D cup breastforms on Ebay. When they arrived, I went out and purchased a sexy D cup bra. Finally one night I started applying makeup and dressing in my new clothes. I was not great at first doing my own makeup, but after a while and some selfies, I improved to the point of being competent. After about a week of practice, I got good enough to apply a good foundation, eye makeup and lipstick. It made a real difference and when I looked in the mirror, I saw a reasonably good looking woman. I have light hair and I wore dark pantyhose to cover up the hair that is on my legs.

I placed a towel over my head and looked at my new self. I decided that with a good wig, I might be able to pass myself off as a woman. I devised a plot. I went to a wig styling shop and told the female manager that one of my friends was undergoing chemotherapy treatments for cancer and that a few of the guys were going to throw him a party when he felt better. Since he had lost all his hair, we were going to all wear wigs as a joke. She seemed a little skeptical, but after some thought, she mentioned that she did have a pretty good medium length brunette wig that someone had not claimed for over a year.

She agreed to sell it to me for thirty dollars. It looked really good. It was not like the novelty wigs you get at the Halloween stores. I was thrilled to get out of there with a good quality wig. When I put everything on that evening, I was stunned. I really looked like a woman. Since my body type was pretty much unisex anyway, the curvy additions made my figure look very passable.

After dressing several times in my hotel, I had a desire to go out in public. One evening I spent about two hours doing my makeup and fingernails. I then donned my sexiest panties and dark pantyhose. I slid the breastforms into my sexy bra and then added the top, skirt and sexy high heels. I looked out the window and did not see anyone hanging around the motel, so I walked out quickly to my car and got in. I drove away from the motel and drove around the city for about an hour. I could not work up the courage to get out. When I returned to my hotel, I got out and walked slowly up to my room. I was so excited when I got into my room. My heart was beating in my throat and my little cock was not hard. I guess it was the fear of getting caught, but I was as limp as a noodle.

Back in my room, I removed the skirt and top, but kept on the lingerie. I read some feminization stories on the internet and my cock slowly came back to life. I had a considerable bulge in my panties and pantyhose. I rolled over in my bed and felt my big breastforms push into my chest. I began humping the bed while the friction played wonders and my silky lingerie slid easily along the clean sheets. Without touching myself, I began to dump spurt after spurt of thick cum into my panties. I had never cum so hard in my life even fucking my beautiful Jessica. I laid a bath towel on top of the sheets and slept the entire night in my lingerie.

Over time, I repeated this scenario many times. I also got a thrill out of shopping for panties and bras while wearing sexy panties and pantyhose under my slacks. I even bought a 38A bra with no padding to wear under my sports shirts. A few times I wore a thin cotton shirt so the outline of the small bra could be seen on close inspection. I got better and better a applying my makeup. I would do everything including fake eyelashes, dangling earrings and plunging necklines. I always had to wear dark pantyhose so my light leg hair would not show. I have very light hair on my chest also so I was not like it looked freaky when I wore lower cut tops.

Part of the thrill became buying the lingerie. I gravitated to going into the major department stores and getting a sales lady to help me pick out lingerie for "my wife". I must say I did get some inquisitive looks, but I eventually became brazen enough to ignore the smirks and quizzical looks. When I returned to my hotel room my heart was racing and I was lightheaded with adrenalin. My little cock would be drawn up to about two inches.

As I became more comfortable with my girlie wardrobe, I became more careless and also accumulated quite a collection. I began saving more and more of the items. I was hiding my things in the truck of my car, but it was a company vehicle, so I was a little uncomfortable keeping several sacks in there. My garage has an upstairs storage area with plenty of room to store unneeded furniture, paint and almost everything else. I found a place among the ski boots, badminton rackets and cargo carrier that I thought no one would ever find. If my wife ever went up there, she asked me to help her move things or take things back down.

Of course eventually she went up there one day when I was gone. By then I had more clothing than I could possibly keep in my car. She found two garbage sacks sealed up and decided to see what was in them. She found my assortment of bras of various sizes, a full range of panties of all description and color, some nightgowns, high heels, spare breastforms, and one blonde wig. When I came home that weekend, she did not mention it to me. Sunday night, when I was packing for another trip, I slipped up to my secret place and was about to re-load my bags with some of my pretty stashed lingerie. I was shocked when I could not find the bags.

I looked everywhere there hoping that I had forgotten where I put them. I knew they were gone, but I panicked. I still had my other items from the previous week in my car. This included my makeup and two wigs along with shoes, dresses and lingerie. I left as usual the following morning. When I got to my hotel that night, I called Jessica, just like nothing had happened. I kept waiting to see if she would confront me. I was not going to ask about the garbage bags myself, so our conversation was painfully normal. The rest of the week was uneventful and I was not in the mood to dress up.

I was to remain at the home office for the next three weeks, so I was waiting for the other shoe to drop at home. Finally Sunday night, Jessica asked me, "Honey, I found a couple of bags of ladies clothing up in the garage attic. They are not mine. Do you have any idea where they came from?"

I wish there had been a trap door in my house where I could just have dropped out of sight. I first feigned ignorance. I asked her if she was sure that the clothes were not hers. I said, "You know women don't hold on to clothing as long as men do. Maybe you forgot you put them there."

To which she replied, "Well the bras were of all different sizes. Some of them were padded, some were not. In addition, I found a pair of cheap breastforms in the size D. The panties were all cute, but I did not recognize any of them. Do you really think I would have forgotten a set of breastforms. My tits are already 36D."

I lied about having to run some errands. I just needed to get away. I drove to a nearby park and parked at one of the picnic areas to plan my next explanation. I tried to come up with a plausible explanation, but I could not see any way I could explain myself. Finally I decided that maybe I would just come clean and see what happened.

When I got back home I told Jessica that indeed all the clothing was mine. I admitted that I had a panty fetish since puberty and that I could not control it. She asked if I was gay. She asked if I dressed up with other people. She asked if I had a lover either male or female. I was stunned by the questions. I told her that none of this was remotely true. I just loved the way lingerie felt on my body and the thought of dressing like a woman excited me to no end. She asked if I masturbated when I dressed up. I admitted that I did. Then she asked why I was unsatisfied with our sex life. I tried to explain that I loved her and I loved her body. I did not want to be with any other woman and certainly not a man.

That night I slept in the guest room. I lay awake all night worrying about whether Jessica was going to ask for a divorce. This went on for the rest of the week. I kept waiting for her to tell me to move out. Finally late in the week, she said, "I guess it's time we talked."

She asked some more questions about how dressing like a woman did not make me feel gay. She was still hurt that our sex life was not pleasing to me. I tried to explain that sex with her was the best I had ever had and that my fetish was in no way an attempt to make up for anything. It was more like an enhancement to me, but definitely hard to explain to her. After the first thirty minutes it became apparent that she was not going to file for a divorce. However, we still had more talking to do.

Over the next week Jessica apparently did plenty of homework on the internet. The next time we talked about my fetish, she seemed more at ease and was very forthcoming about her own ignorance regarding the subject of male to female crossdressing. She said that one of the things she read indicated that up to 10% of men liked to crossdress in some regard. She also indicated that she was surprised that 70% of male to female crossdressers are straight. I told her that I did not know any of this, but that I was indeed straight and love sex with her.

Finally we were back to normal. Jessica started a little foreplay one evening after I got out of the shower. My cock was a little slow to respond, but with some coaxing she got me hard. She sucked my cock a little, then straightened up and said, "Honey, I so want everything to be like normal with us. I love you and I have been thinking about your little fetish. The more I think about it, the less it turns me off."

She related how some of her girlfriends were already divorced. Some of their husbands had cheated on them and a few had cheated on their husbands. After considering all the unfaithful spouses and some of the misery they had gone through, Jessica told me that my fetish was so tame that she had reconsidered how it made her feel.

She said, "You know, after I got over the initial shock, I thought about you masturbating in your girl things and it actually started turning me on. Would you wear some of your things for me?"

I was embarrassed and my cock started to go soft. I told her that I was not going to do that anymore. She surprised me by saying, "I know you feel embarrassed by getting caught, but I wanted to tell you that I think of you masturbating in panties and I want to see it for myself."

I confessed that when she had thrown out my attic stash, I had thrown away all my girl stuff and vowed to abstain.

She then apologized to me for not being more understanding and more open to my needs, even the ones she did not understand. She said, "What a shame to waste such a collection and you had some very pretty stuff too." "How about I get a pair of my panties and slip them on you?"

I could not believe that she had come fully around to actually wanting to see me in panties. She got off the bed, went to her dresser and pulled out a very pretty sheer pink panty. She came back over and began sliding them up my legs. She pulled them up past my balls and my cock just made it out the top of the elastic. The panties had lace panels running down the front sides and otherwise were very sheer. Jessica pulled my hand down to my hard cock and led me to slowly stroking myself through the panties. After I moved my hand up and down my shaft through the sheer panties, she began rubbing my chest and kissing me.

She said, "That's it big boy, stroke that cock for Jess, get him good and hard to fuck my tight pussy. Yes, go on and spank that monkey, sweetie, I can hardly wait for you to shoot that cum out of your cock."

I was really getting into it now. I was as excited as I had ever been. My cock was leaking copious amounts of precum. It was shining on my belly as my cock pushed more and more out. I had never had so much lubrication ever before. Jessica moved her hand down and felt the precum leaking out. She said, "Oh, yes, your are dripping wet. Stroke that cock and cum for me."

Suddenly my whole body convulsed and my cock began shooting cum up my belly and chest. The second pulse hit me in the chin. The third ran under my chin and down my neck. Spurt after spurt blasted my body as Jessica shrieked and moaned.

"Oh, god, look at all that cum. You look like a pornstar shooting all that over yourself."

She took my hand and moved it up my torso. She began sliding her fingers over the swamp of cum and got me to do the same. We played in my cum until it was starting to dry on my body. My cock finally started going soft and continued leaking cum into the sheer panties. Jessica was moving my hand back down into the slimy mess in the panties and following with her hands too. She laid her head on my stomach and continued to slide her fingers through my own and into the slimy nest. My cock and balls were coated with my cum and it was leaking down the crack of my ass.

We rested for a twenty minutes and then Jessica said, "You better get ready panty boy. Now I am going to get mine." She began rubbing my cock again. I was ready to go and my cock had no trouble rising to the occasion. She pulled my panties down and began stroking me again. When I was hard enough she mounted me and began riding my cock with unusual vigor. She reached down and guided my hands to her beautiful breasts. I circled the magical orbs and tweaked her nipples. She bucked like a cowgirl and finally slid her hand down to her clit. She began moving her fingers into the union of my cock and her pussy, finding the hard clit and pressing her fingers into in. She shrieked and straightened out over making sure to keep my cock in her wet pussy. We lay that way until my cock slipped out as it shrunk.