Beth and I enjoy a complicated sexually uninhibited relationship. I have an athletic build but not muscular, and I am just under 6 feet tall. Beth is gorgeous and has long straight Auburn hair, physically in great shape, and C cup breasts. We had been in an open relationship for over 2 years when one night, she and her girlfriends introduced me to cross dressing. It was a wild night that involved makeup, panties and strap-ons. Following that evening, Beth would work cross dressing into our routine and it became a more regular occurrence. Beth would occasionally ask me or tell me to wear a pair of panties and sometimes a bra that she selected to bed. Sometimes it was part of role play when she would be in charge and would use her strap-on. Other times, it just turned both of us on and led to incredible sex. Regardless, I almost always spent the entire night in her panties.
I’d like to say I am as uninhibited as Beth, but she certainly opens my mind to new experiences. And I won’t lie and say the feeling of panties and a bra wasn’t exciting. At my work I am a manager and decision maker, so to assume a completely different submissive posture or behavior was kind of liberating. One Friday night, after a long incredibly exciting time in the bedroom, we lay in bed together, me in a teddy, both of us dressed in her panties, and Beth topless, when she rolled over and asked me to wear panties all weekend long. I agreed, and it led to a weekend of excitement. Saturday morning Beth got in the shower along with me and we explored each other and then she said I should shave along with her. Without a thought I joined her and did my best to shave my armpits, chest, legs, groin and ass. It wasn’t easy and I nicked myself a lot. I got out, dried off, and felt my skin. My legs were smooth and armpits clean, but I could have done better around my genitals. I put on the panties that she selected. Every step I took that weekend, I felt the panties against my ass and between my legs, sliding across my cock which spent the duration in a semi hard state. And each night Beth ensured the sex was sensuous and exhilarating.
These weekends became more frequent and occasionally Beth would reach into my boxers and comment on how smooth I was or wasn’t. She started to buy products for me. It began with moisturizers and skin care lotions and progressed to hair removal products such as Nair and waxing strips. Sometimes during the week she would suggest I wear panties to bed and it seemed when I did, it always led to a late night of fun sex. Conversely, it started to seem that if I didn’t wear them to bed, sex was unlikely unless Beth was very worked up about something. As time progressed, I was keeping my body free of hair daily and wearing panties every night. And having incredible sex. Beth then suggested that I wear panties to work, just to build the anticipation and excitement throughout the day. It was an incredible distraction. My erection was held in by only a thin layer of lace all day and I spent a good part of my day wondering if people would notice that, or any panty lines, for that matter.
Nearly four months had passed since my first experience cross dressing and I was now wearing panties every day and night, keeping my body smooth and using women’s skin care products daily. I had always worn my hair long as a guy, kind of all one length and combed back, but I had not had a haircut since well before that evening and my hair was now creeping to, if not past, my shoulders. When I dressed on the weekends, Beth started to refer to me strictly as Kelly.
One Friday, Beth called me at work and asked if I wanted to go out to dinner at one of our favorite restaurants close to our house. I thought that sounded great and looked forward to having a nice burger and a few beers. I arrived just after 5 and headed toward the bar to wait for Beth, but as I passed the greeter at the stand, she said Beth was seated out on the patio. I headed to our table and sat down. Beth had ordered us drinks and when they arrived it wasn’t beer, it was a vodka cranberry drink. I told Beth that it wasn’t bad but I had planned on a beer, to which she replied that beer was unbecoming. A bit surprised I asked what she thought about the burger I planned to have and she said that we would be having salads. Ok, I can be healthy, but that didn’t sound like it would satisfy my appetite. It turned out everything was very good, albeit I would have liked more, and we talked about our week before Beth turned to our weekend plans. She said we would be spending the weekend as girlfriends. I panicked thinking she had plans to take me out publicly but she assured me we wouldn’t do that. She did say though that we would have some different experiences. With that she said ‘let’s go.’
We hopped in her car and drove to the mall which was only 15 minutes away. But as we drove, I asked why we’re headed there this late when the stores were closing in less than an hour. My question wasn’t answered until we walked through the mall to the Victoria secret store, in one of the more prominent locations. Beth said it would be easier to shop when there were less people and I would be less concerned about other customers. A young strawberry blonde girl with light freckles approached and said hi to Beth. They obviously knew each other, and quickly I came to realize that they had discussed me and the role playing Beth and I were into. She looked at me, put her arm around me giving me a quick hug and then saying, ‘Hi, I’m Sam, and Beth tells me you go by Kelly. We will be discreet, but I’m going to help you pick out your own bras and panties and I hear some lingerie as well. How exciting!’. The shock kept me from saying anything. Someone else knew? ‘Again we will be discreet’, she continued, ‘but let’s talk about what you are looking for today’. I was still in a whirl as Beth told Sam that she wanted me to select at least a weeks worth of bras and panties, she wanted matching sets, she wanted me to experience different fabrics, but they all needed to have enough material to hold my ‘clit’ inplace as well as allow me to tuck. She wanted me to have a mix of styles, but they all needed to be a little racey, no straight bikini briefs. They turned to the lingerie and Beth said we had to remember my breasts would need support but she wanted me to have some variety of style and color. They talked about teddy’s, bustiers, corsets and camisoles.
‘Ok’ Sam said, ‘Let’s talk sizes. How do the panties you have on right now feel? And what size are they?’. I could have passed out right there. She continued, ‘Look, I think Beth has told me everything about your journey. That should make you feel good, there are no secrets to spill or anything to keep concealed. And I am too good of a friend to Beth to think that I’m going to shout it out in the store’. I took a deep breath, soaked in the look Beth was giving me, that look that asks me not to disappoint her, and I described the fit. The fact that the panties were tight, and they didn’t seem to ride high enough up on my hips, and I’d prefer them to be snug. She asked about the bra and I told her that it was pretty tight and I could barely get the bra clapsed on the last hook. She and Beth discussed sizes, Beth told her that she wanted D cups, they agreed on what size I would be and away we went. The ladies shopped and found different sets and asked my opinion, in a few cases holding them up to size me up and look at the material and fabric. In under an hour I had 8 bra and panty sets, and a variety of lingerie.
When we arrived at home we were in a sexual frenzy. We walked in and Beth told me to take her clothes off. As I lowered her panties, she said that wasn’t exactly what she meant and told me to take her clothes off of me. He were both naked and she reminded me that we were spending the weekend as girlfriends in every way. We groped and fingered and licked and sucked each other in every room for hours, bringing each other to orgasm several times without me penetrating her before passing out naked.
In the morning Beth told me to take a shower and that when I was done she had a surprise for me. She told me that I should wear my new pink thong and matching bra. Once I had them on she pulled out a white box, slightly smaller than a shoebox and aerosol can. She asked me to slide my bra straps over my shoulders. She opened the box and there were two fake breasts in the box. They looked pretty real, and they felt real in mass and to the touch. She sprayed the can onto the back of each breast and pressed each against by chest as she pulled up the bra strap tight to hold it in place. The adhesive quickly dried and the breasts were fully in place. She went to the other room and brought in a few more bags. She pulled out two tank tops which I put on in a layered fashion and then she pulled out black yoga pants. I put it all on and Beth told me I looked cute. I told her that I didn’t think my ass looked great in them, and she said we would work on that. I brought two chairs into the bathroom at her request as she pulled out all kinds of makeup. We sat side by side for almost 3 hours learning how to properly apply it. In the end, l learned how not to over apply the products and I thought I looked pretty. I don’t know if I could take credit for it, but I looked much more feminine and passable than I ever had.
I stood up, my heavy breasts protruding, the yoga pants hugging my legs and ass, my made up face and lips. I told Beth that I had to do something with my hair. She said we would, but then pointed and said I need to do something about my erect clit. And I was hard like a rock. She had me peel off my leggings and thong. She had me close my eyes and told me to pretend that Kelly was at home with her boyfriend and was standing in front of him and his erection. At first she told me how to use my hands to stroke and hold and play with the erection. But then she had me describe what I was doing and how I was caressing and stroking and bringing that cock to climax. She asked me if I would take it in my mouth and as I said yes she put her lips around my cock and I exploded in her mouth. She motioned for me to kneel and she leaned forward and kissed my painted lips and pushed my cum into my mouth. She told me I deserved it since I worked so hard to earn it.
She had me get my thong and yoga pants back on and had me tuck my softened clit between my legs. It was uncomfortable and it kept coming loose. Beth told me to try keeping my thighs closer together but if we need to, we could use body tape later. She had me fix my makeup and then took several of the makeup items and put them in a small bag and then into a purse.
We left the bathroom and Beth had a few more bags. She had bought me shoes. A pair of white tennis shoes with pink accents, closed toe flats, and a pair of high heels, maybe 2 inches. She had me put the high heels on. She told me the heels were shorter than most, but she didn’t want me to be too tall. She had me begin walking around the house and it was incredibly awkward. She made me continue to walk, giving me pointers, until she was satisfied with my movement on carpet and on tile. I took the heels off and my feet and calves ached. As I sat down there was a knock at the door. Before I could say a word, Beth flung the door open and welcomed in a person she introduced as Lisa. I learned that Lisa was her friend that cut her hair, she had long black hair, a face more round than Beth’s and was a little more voluptuous in shape. She had a loud voice and walked in and hugged me and said ‘well I hear that you are Kelly, I’m Lisa. Beth asked me to come take care of your hair and teach you how to style it a few different ways’.
I couldn’t believe it. Someone else knew. I looked at Beth and her smile told me to sit down and enjoy. Lisa and Beth talked about my hair style. Beth wanted to ensure that my hair could be pulled into a ponytail, or styled around my face, and also wanted to ensure that I could style it for when I went to work. And that was a relief for me to know they still understood I needed to maintain my gender at work. They debated bangs or no bangs for a bit and then decided no bangs. Lisa cut my hair, not taking much off by the looks of the kitchen floor, but taking quite a bit of time. When she thought she was done cutting, we moved into the bathroom. They plugged in a curling iron and started to discuss how to style as a guy, which consisted of combing my hair straight back and using gel, and that did work by the way. As I looked into the mirror at my dirty blonde hair, they had me blow dry it using a brush, continuously brushing as I dried. My dry hair ended up coming down to the top of my shoulders. It was noticeably layered. Lisa had me put waves in the lower half of my hair, starting just above my ears, all the way around. Each time, I twisted the hair a couple of times around and held it 5 to 10 seconds and the hair bacame wavy. I couldn’t believe the transformation. Beth asked if I wanted to quickly wash my hair and do it again on my own, but I declined, thinking I could handle this.
Beth then told me to comb my hair out and put it in a ponytail. I did, they helped, and they both thought that the layers of hair that hung out of the ponytail were cute. So here I was, made up, lipstick on, hair in a ponytail, 2 tank tops over a pink bra holding D size breasts, yoga pants covering a pink thong with a hidden away clitoris, and white tennis shoes with pink accents. This was the first time I truly saw Kelly.
There was a knock at the door and this time I didn’t panic, I simply wondered who else knew. Beth opened the door and Carolyn walked in with dinner. Beth introduced Lisa and Carolyn and asked Lisa to stay for dinner. Carolyn complimented Beth on my appearance. During dinner, the girls counseled me on how to sit with legs crossed and back ever so slightly arched, how to stand to show off my hips and ass, and how to act in different situations with men. Carolyn told me that while I looked like a woman, I sounded like a man. They made me work on my voice through the rest of the evening and by the end of the night they said I sounded more like woman even though I thought I still sounded like a guy. Lisa left after dinner. As we drank into the late hours of the night, they had me wear my heels and practice walking, telling me to step one foot in front of the other and to feel my hips sway side to side. While I still had my heels on, we practiced dancing, quick songs where they had me work on the twisting and rotating movements of my hips, including arching my ass out, as well as slow paced songs where I practiced pressing my body into my partner while following their lead.
Eventually the ladies allowed me to take my heels off and we sat and talked more. The talk turned to men and what they looked for in a partner. The girls eventually asked me what I was looking for in my first guy. I told them I wasn’t interested in finding my first guy, that this was an erotic experience but I didn’t intend for it to be more than that. Carolyn laughed, ‘Look at you? What do you mean you’re not interested in your first guy? How long have you been wearing panties? You have your own now. You are wearing women’s clothing, you’re madeup, you have a feminine hair cut! Who are you kidding? This isn’t foreplay anymore. You need to go look in the mirror and be honest with yourself. It’s just a matter of time before you suck cock and let a guy fuck you in your thong panties’. Beth interrupted and provided her view, ‘I personally think everyone is and should be bisexual. You know I enjoy my experiences with women just as well as men. Why can’t a man explore his feminine side as well and have sexual experiences with men? I’m glad you’ve tried this and I think you should go further, I promise you won’t regret it if you do it right. But Carolyn is right, you do need to be honest with yourself’.
That seemed to bring the evening to an end. Carolyn left abruptly and Beth and I got ready for bed. Beth had me remove my pink bra and she helped me put on a black sports bra that she had bought for me. She wanted me to sleep with my breasts on and the sports bra held them firmly in place. I thanked Beth for the day and all she had done for me and all I had learned. She told me to close my eyes and think about sleeping next to a real man after having given myself to him. The next morning, and every Saturday and Sunday morning for that matter, Beth had me get up, shower, do my makeup and hair and fully dress, as well as practice walking in my heels. Sometimes I would remain that way, other days I would change and we would go out. If we were out, Beth would comment on the different guys at the bars or restaurants and ask my opinions. I resisted at first but as time went on I succumbed and would provide some response to her commentary. My diet was more responsible and I rarely had beer. Beth continued to buy me additional outfits as well as bras and panties, and she bought me some jewelry as well. And while she continued to walk me down this path, we were having less and less sex.
Source: reddit.com/r/gonewildstories/comments/rxqqfk/kellys_first_part_1_fmm