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My journey from Steve to Stephanie
I have always been fascinated by girls clothing. It might have started when I was just a kid sharing a bedroom with my sister. There is one event that stands out. Because my dad worked shift work and was sleeping in their bedroom my mom and sister were getting ready for church in our bedroom. They thought I was asleep so they didn’t even turn the other way when they each pulled off their nightgowns and put on their bras. Pantyhose hadn’t been invented yet so I also watched with interest as the put on their stockings and attached the garter belts. I became enamored with boobs, bras, stockings, garters and all things feminine.
A few years later when I was an early adolescent teen I had a paper route. Along my route were some multi-family homes. Giant houses from the WW-II days divided into apartments for four families. They were slated to be torn down so all the residents had to move out and in the weeks before demolition they were open and empty. I went exploring and found one two story apartment where all the furnishings had been removed but much of the personal belongings remained just dumped out on the floor. In one of the upstairs bedrooms I found lots of ladies clothing along with a photo of an attractive Asian lady about my same size. I took off my clothes and tried on hers. I remember there was a white girdle with garter hooks and some stockings that felt especially good. Her bra size was small maybe 34A or something she had some white and one black ones. The black one had lace and demi cups so it felt really sexy. I stopped by and tried on her stuff and jacked off in her bedroom several times that summer before they finally tore the building down.
Fast forward 48 years, I am now old and my Hotwife is now more interested in sex with her boyfriends than with me. Its been over a month since we had sex together. When her boyfriend comes over I lay nude in the next room and listen to their foreplay and fucking. He is a machine and can make her cum many times. Sometimes I listen for 30 minutes or more before I hear that sweet sound of him cumming deep into my lady. He usually shoots 5 to 7 strong ropes before he rolls off and tells me its my turn. When I go to her she is still spread and without a word she gestures for me clean her up. I’m expected to lap up every drop and probe her deeply with my tongue. She always cums a few more times as she squeezes all his load back into my waiting mouth.
One day while I was alone shopping for our groceries at one of those superstores I wandered into the lingerie department and found the sale rack had some really sexy red lace panties just my size. I also found some inexpensive thigh high stay up stockings. I looked at the bras but nothing was my size since I have filled out a good bit compared to those early adolescent days in the Asian lady’s apartment. I place the panties and thigh highs in my cart and quietly checked out. I tried them on at home alone and loved the way they felt and even more loved the way they made me feel. This was the beginning of my cross-dressing days.
I became obsessed with trying on ladies garments. I found that thrift stores were the perfect place to browse interesting things, the feeling of trying on some unknown ladies things returned and excited me. I began to accumulate several wardrobes, panties, short tight or loose sheer skirts, silky low cut tops. I even found a couple pair of high heels that sorta fit. I bought a red garter and a blonde wig and some jewelry. I even tried lipstick, eye makeup and nail polish. I keep all my kinky clothes hidden and eagerly anticipate my Hotwife’s out of town trips so I will have some freedom to dress. I make a butt ugly Gurl but if you can get past that it is a lot of fun.
I’ve found that I really like being seen by other men while I am dressed. Its hard to find guys who appreciate a Gurl but some really get into it, pardon the pun. I bought a butt plug trainer and began practicing with it, fantasizing what it might be like to truly experience all there is to being on the receiving end as a Gurl. There have been a few 1 on 1 meetings and a few walk throughs of an Adult Book Store. Those took a lot of courage and were quite thrilling. No one beat the heck out of me, some looked away and some just looked and made a sexy noise as I passed them.
The most fun I had was one morning as I was travelling. I had all my frilly clothes with me and stopped at a large ABS in another state. I had bought a thrift store purse and places all my frillies in it so once I was back in the peep show area I went into a both alone, locked the door and transformed myself from Steve to Stephanie! When I emerged I was wearing crotchless panties which were great because my member and balls would protrude through the slit and be surrounded by soft lacy fabric on all sides. I wore my red garter and black thigh highs, my white high heels and a very short black skirt. My red silky top which had rhinestone buttons up the front covered my red lace bra which unhooks in the front. I had on a necklace and bracelet, some red lipstick. The real attention grabber was my long blonde wig. In the dimly lit ABS I had become a head turning Stephanie!
It always takes me a few steps to get the hang of walking in heels without tipping over and today was no exception. As I strolled down the peep show hallway with my purse on my arm filled with the clothes I wore in, I heard several men softly whistle or say – you look hot. I found my way to the straight theatre room and sat down on one of the sofas that wrapped around the back corner of the theatre room. I put my purse beside me and crossed my legs in a most lady like manner as I began to watch the movie. Very soon several men took seats near me but still not close. I pulled my hair back and uncrossed my legs and re-crossed them several times as I’ve seen ladies on the hunt do in bars over the years.
Soon a large black man came and sat to my immediate left and his friend another smaller black man sat to my right. I moved my purse to the floor behind my legs and they correctly understood that as a signal to scoot closer. The one to my left placed his hand on my thigh first as I uncrossed my legs. He slid his hand up my stocking to touch my bare leg above and I began to moan my approval. His buddy also placed his hand on my right thigh and together they spread my legs as they caressed my thighs and each took turns also caressing my growing manhood. The one to my right caressed my breast and began unbuttoning my top. He said I looked really good and proceeded to unhook my front snapping bra. They each leaned in to suck on a nipple as I noticed a crowd had gathered to watch. My skirt was pulled up by a third person as he went down on me. I had hands, lips, tongues probing all my fun spots or so I thought.
Soon the guy to my right moved to kneel between my legs and was replaced by another older white guy to my right. Soon my legs were raised high in the air as I was slid down t the edge of the couch. The guy between my legs moved from my cock to my asshole and began to lick and probe with his tongue. His friend to my left was holding my leg high while he pinched my nipple and then leaned in to French kiss me. Soon I felt a finger , then pretty soon two fingers probe me. I was being lubed and groped from every side and loving it. About that time one of the guys standing to watch the action shot his load of cum several feet and I felt it hit my stocking and the bare leg above in several spurts. The guys groping me gave that guy a look and if they hadn’t been so busy might have had an issue with him. He backed away tucked and ran. The guy who had been fingering me stopped and suited up with a condom. His friends spread my legs as he entered me. In spite of their prep, my virgin ass was tight so he had to push really hard to get it and it hurt like heck. The guys holding my legs up caressed my thighs and pinched my nipples to take my mind off my ass as he began pumping. Soon the pain was gone and pleasure began. With all the caressing and fondling by several guys at once and him hitting my G-spot with his strokes. It wasn’t long before he came.
As he pulled out an older white guy to my right leaned in to kiss my ear and whisper that I was beautiful and he would like some time alone with me. The two black guys left and I straightened myself up as the older white guy caressed my right thigh. It felt good so when he took me by the hand and stood up, I stood with him. My legs were weak and I was wobbly in my heels but he held my hand and helped steady me. I grabbed my purse which had my street clothes, wallet and car keys and we walked off to find a more private location. He seemed to know the layout well and found a booth without a Glory Hole and he led me in, locked the door and began to kiss me. He groped and caressed me all over as he kissed me and told me how beautiful I was and what an exceptional cock I had as it was now fully erect from all the stimulation. My skirt had a mountainous bulge in the front. He began to undress me as he continued his assault on my breasts, my neck and my ears. I was so turned on. He very gently caressed my nipples making my cock twitch and toes tingle. He took my pre-cum and used it as a lube on my nipples to stimulate me even more as he twirled his finger on my nipples.
I was now nude with him except for my stockings, garter and heels. He gently pushed me down to my knees and I began unzipping his fly and undoing his belt and pants. The whole time he was telling me how beautiful I was and how happy he was to find me. I wanted to return the favor and make him feel really good. I was very pleasantly surprised with the size of his cock. I tasted his precum and caressed his cock with my tongue. I was glad I had thought to put ribbons in my hair to keep the wig out of the way. I began to suck and deep throat him and I was really determined to make his toes curl. He stroked me and pulled me up for an occasional deep French kiss before pushing me back to my knees to finish my job. After several minutes I heard his breathing get shallower and quicker and I knew he was about to cum. Stream after stream burst down my throat and I swallowed as quickly as I could to keep up. I think I counted 6 or 7 bursts of his cum before he slowly began to grow soft and pulled me to my feet. He hugged me, held me close and told me again how beautiful I am. He smacked my ass a couple of quick times and said thank you, thank you, thank you. He gave me a card with his name and number and said he hoped to see more of me. He left the booth and I locked the door behind him.
I sat in the dark with the straight porn movie playing for a while and stroked myself. After a while I was soft again and got dressed in my frillys again to walk the halls some more but there was no one around who seemed interested in a gurl so I got back into my street clothes and was on my way.
I love being appreciated and treated this way. - DownLowBiGuy aka Stephanie