How it all started

How did I become Kelly? Well this story details one night that certainly sent me on this journey. To get started, you need to know a little background. I went to a large Midwest college and really enjoyed myself. I received good grades but partied alot and had many sexual experiences and really learned to put inhibitions aside and explore. About 5 years after graduation, I had become a manager within my company and was responsible for about 20 people. I ran alot, athletic build but not muscular, and I am about 6 feet tall. I was in a relationship with a woman named Beth going on 2 years at that time. Long straight Auburn hair, physically in great shape, C cup breasts. We each had a place but she really just lived with me. She was more uninhibited than I was. She was a sexual animal, once we started it was likely that we would be up all night. She was easy to please and wanted to please as well. She liked different things and she wanted it to be different every time. And nothing was really off the table. We had an open relationship, that was her request. I really wasn’t that ok with it, but it was part of the deal and I didn’t want to give up my time with her. We were together more than 90 percent of the time, but there were always those occasional nights where she said she was out on her own and not coming home or asked me to stay elsewhere so she could have friends at our place. She always shared the details, there were no secrets. If you have ever been in an open relationship, you may have struggled like I did, but after a year of her always coming back to me with the same energy and desire I kind of became ok with it. I had a few one night stands while she was out on hers, but mostly it was guys night out drinking.

This was one of those nights where Beth had asked to use our place to have the girls over. She intended to have 3 friends over, I assumed to drink and then head out to see if they could find more fun. We lived a short drive or a long walk from a small bar scene. I should tell you about the group.

Amy was Beth’s roommate for 3 years in college (Beth and Amy went to a different college than me). Amy was very similar in size to Beth, maybe a little bigger breasts. She had dirty blonde wavy hair, green eyes, a great smile, funny, easy to talk to. They were close and Beth had shared that they often explored each other while in school. Amy was now engaged to her boyfriend who was now an officer in the army.

Carolyn was the wife of my fraternity roommate Dave in college. Carolyn had spent a lot of time in our room and we had been to many parties together. Dave traveled for business and he wasn’t very faithful to her and she in turn was not to him. Carolyn looked good. Petite. Perky breasts. Brunette, but died her hair blonde. She had an edge to her. She could be incredibly friendly and then incredibly bitchy. Carolyn and Beth went to high school together and Carolyn introduced me to Beth.

Jen was the final piece of the foursome. She didn’t really fit in. She was the girlfriend of one of Carolyn’s guy friends. She always seemed a bit trashy. Smoked, smelled like an ashtray. She had dark brown hair, a bit heavier than the others but certainly not unfit.

I worked late that night and walked in finding the 4 ladies sitting in my living room. Beth was in our recliner and the other 3 were sitting on the couch. I had completely forgotten about the plans. I apologized and said I would change and be on my way. I called my friend that I had planned to meet and found out that my plans had fallen through. Oh well. I figured I would go find some food and then head to Beth’s place and have a few drinks there and just get some rest. I asked her for the keys and she asked questions until she figured out my plans had fallen through. ‘Its just girls night, why don’t you just hang out with us?’ she said. Carolyn quickly added ‘But you’ll have to be one of the girls’.

I figured why not. I can make them drinks, hang out, stay out of the way. The conversation was interesting and fun. Alot of catching up between the girls, but everything had a sexual edge to it. At one point the conversation turned to shaving. Turned out that all but Jen were clean shaven but the question was then posed to me. And while I keep myself trimmed I was not clean shaven. Then I was asked how I prefer Beth and I immediately replied clean shaven, it’s just so much easier to tease with your tongue that way. Well now I was a hypocrite and they were having none of it. Carolyn demanded that if I wanted to be fair, if I wanted to be one of the girls tonight, I need to go shave. And Beth and Amy and Jen all wanted that as well.

Again, why not. So I went in the bathroom, took my razor and got in the shower. I did my best to clean myself up and make sure everything was smooth. When I was done, I opened the shower curtain and the women were all there waiting. I was told to turn around and as I did I received a lot of commentary about how unacceptable it would be for a woman to be satisfied with that shave. Beth undressed in front of everyone and got in the small shower with me. She turned on the water and directed me to shave my legs, my chest, underarms, etc. She inspected and then took the razor. She shaved my ass and my testicles, thank goodness gently. I was virtually hairless. When the curtain opened the ladies approved. Amy helped dry Beth off while Carolyn and Jen watched me.

I looked around for the clothes I had taken off and Carolyn said if I was going to be one of the girls I needed to dress like one as well. Now I was unsure how much farther I wanted to go. But Beth encouraged me and reminded me that we had just shaved me in front of everyone, so they were part of the fun, and we weren’t going out. So what’s the harm? It’s a new different experience, right? She disappeared into our room and came back with a pair of black satin panties, a black bra and a black teddy. I dressed in front of everyone and the feeling of the satin on my clean shaven skin made me become aroused. Carolyn noted that the cups of my bra were empty and went into my room. She returned with thigh high stockings and told me to put them on. She then went to the kitchen and returned with 2 black balloons filled with water and stuck them in the cups of the bra.

My arousal was now a full erection and quickly gained the attention of every one in the packed bathroom. Amy reached down and stroked my ‘clit’ as she referred to it through the satin. Her light touch and use of her nail tip through the satin had me on edge. She then stopped and told me that many times women have to take care of themselves, that their men finish before they do. Beth pulled me close to the bathroom counter and mirror. ‘Look at how good you look in my clothes! You’re adorable. Play with your clit through your panties. Reach inside and stroke it. Finish yourself’. I did what she asked. I was so caught up in the moment, so free of any inhibitions. All I could see is my satin covered body in the mirror, Beth and Amy. Their hands ran all over my body and soon I was on the edge of coming. I was pushed close to the counter and soon shot ropes across it, some reaching the mirror. As I relaxed, Beth wiped the residual off of my tip with her finger before she put it back in my panties. She brought it up to my mouth and pushed it in.

As my excitement came down and as I stared at Beth, I heard Jen and Carolyn directing me to clean up after myself. There was a lot. I turned to grab some Kleenex but Jen demanded that I lick it all up. We’ve all tasted it she said. You just did, referring to Beth’s finger. ‘Now use you tongue and get as much in your mouth as you can before you swallow’. I stood there for a moment and Beth leaned in and told me to do it. She guided me close and I did. I used my tongue and licked the mirror, the counter. I didn’t have a mouthful, but there was enough and I did well not to gag. Beth told me to swish it around my mouth and then open for them. Jen cleaned what I missed with her finger and wiped it across my lips and into my mouth. Beth told me to swallow. And I did.

‘You’ll never be able to say you haven’t swallowed a man’s cum now’ Carolyn said.

Amy brought a chair in the bathroom and sat me down on it. There was no discussion, the girls just went to work and did my makeup and hair as good as they could to transform me into their girlfriend for the rest of the evening. They talked amongst themselves, discussed makeup choices and talked about clothes they may have me wear. Beth leaned in and applied lipstick. I looked in the mirror. I didn’t look like a man anymore, but I also didn’t look like a slut. I also didn’t think I was an attractive young woman either. Jen told me to stand up and bend over the counter and put my face as close as I could to the mirror without touching it.

Carolyn told me that I should get familiar with this position, bent over, ass in the air, ready to be taken. Ready to be felt up, to have my panties pulled down, stripped and used in all my holes. She told me not to move and pulled my panties down and firmly pushed a plug in my ass and pulled them back up. It felt huge and filled me up. This wasn’t the first time I had this experience. Beth and I experiment with bdsm and she purchased a strapon a while back and had used it 3 maybe 4 times when she was the dominant role. She would wear the strapon and also insert a vibrating egg into her pussy. The more I would moan and talk dirty, the higher she would turn up her vibration, if I became quiet, she would turn it down. She would fuck me until she came, so you can imagine the dynamic that created. As for my pleasure, she would direct if I touched myself and when or decide if she did. And if she came before I did, sometimes she would tell me to finish myself while she watched, other times she would tell me not to finish and to go to sleep.

‘Now the girls can hang out’ Carolyn said and Beth led us all back into the living room. We all had wine, although I would have preferred a beer. I served the ladies while we all talked and listened to music. It was odd yet oddly arousing. My ass was still full, but the satin still felt good as well as the stockings on my legs and thighs. It was just after 9 and I was getting light headed from the wine after not eating dinner and going through all of this change.

While I was opening another bottle of wine, Amy suggested that everyone get as comfortable as I was. As I walked out of the kitchen I saw Amy cuddled up next to Beth on the couch, nearly on her side, one leg on Beth’s, her hand on her breast. Their time as college roommates was being re kindled. They were quickly in their own world, passionately kissing, hands roaming. I didn’t take long for them to start removing each other’s clothing. Carolyn moved off the other end of the couch in order to give the former roommates all the space they needed. She removed her Capri pants, and sat on the ottoman in front of Jen. Jen reached out and unbuttoned Carolyn’s blouse.

I set wine down for everyone, Carolyn started to talk with Jen and I about the times she spent at our fraternity, all the parties we went to, some pretty sexually charged moments. Meanwhile, Beth and Amy were escalating, Amy had only her green panties on and Beth was completely naked. Soon Amy was between Beth’s legs. Carolyn took note and told me to sit on the floor in front of her and remove her panties. I reached forward, she lifted her hips and I slid them off. She pulled me into her lap and instructed me not to disappoint her. I knew how to pleasure Beth and I applied the same techniques and soon Carolyn was squirming and moaning, and after a while, she was grabbing my head and spasming. I was pretty pleased with myself. When I pulled away I could see Beth and Amy had switched positions and I could tell Beth was on the verge of orgasm.

Carolyn told me to go fix my makeup and come back. That was something I had never done before, but I did, and I was surprised at how much attention I paid to the mirror and myself trying to get it right. I became more aware of the heavy water balloons that were my breasts and weighted my bra and chest. I fixed all my clothing, my hair, well that didn’t look great but it was about as good as the girls could have done with hair that was long for a guy and short for a woman.

As I got back to the living room, Beth asked Amy if she had brought the toys. They released their embrace and Amy went to her duffle bag that she brought and opened and removed a drawstring back. I watched as she pulled out 4 strapons, all the same size, I think all were different shades of nude to black, and I was sure all were bigger than the one Beth had in our bedroom. ‘One for each of us’ Amy said. Beth told me I didn’t need one. The women were all undressed at this point. Amy helped Beth put hers on and then the two girls embraced, kissing before Amy laid back on the couch and spread her legs. Beth pressed the large dildo to Amy’s pussy, slowly moving it up and down to lubricate it and then very slowly inserted it with slow short thrusts, each one going deeper than the last. Each thrust told me more about their time together in college.

Carolyn and Jen both put their strapons on as well. Carolyn called me over and asked me if I was impressed with the size. She told me to wrap my hands around it. She told me to stroke her and Jen’s cocks. She told me to get on my knees and wrap my painted lips around the shafts and get them lubricated. I saw no point in arguing so I did as told. While I could get my hand around the dildo, it was large in my mouth. I had to suck both Jen and Carolyn’s members and my over applied lipstick left marks on the shaft and I was told to take more and more with each motion. Not that I should have been proud of this, but I was able to suppress my gag reflex after a bit and take more and more until my nose was touching Carolyn’s a stomach. I was coached on eye contact and told to stroke the cock I wasn’t sucking. Carolyn demanded I stare at her face and hold still and she began to thrust in and out. As she did so I heard a few clicks and Jen said she had gotten a few good ones. I panicked as I realized they had taken pictures but I couldn’t protest as she held my head and continued to work my mouth.

Finally, she lost interest in the activity and pulled out. She told Jen to bend over and instructed me to lick Jen and use my tongue to open her up. She then position her well lubricated dildo at Jen’s entrance and began to fuck her. All four women fucked for what seems like hours, mostly staying paired up. Beth and Amy were more passionate and romantic and gentle, while Jen and Carolyn were more quick and rough. I was occasionally summoned by each pair to suck clean their dildos or lick their clits, but my involvement was limited. Carolyn and Beth spent some time together but eventually the women all took a break. I was told to get everyone a refresh of wine.

The scene was interesting. Lights were on, there were four naked women, all wearing strapons, Beth and Jen were standing, members swaying in front of them, Amy sat like a lady on the couch with a huge erection and Jen was on the recliner with her legs spread, one over the arm of the chair. The music continued to play and Beth asked me if I liked what I had seen. ‘Of course I did.’. ‘Good’ she said ‘because your turn is next.’ She then suggested that each women fuck me in a different position to finish off the evening. She went into the bedroom and returned with the egg. ‘You know how this works right?’. She explained the arrangement to her friends. ‘You’ll have to lube each of us up before we take you. And whoever goes first will need to start slow and be easy, we don’t want to hurt her.’ Carolyn said she wasn’t going first then.

Amy was laying on her side on the couch. She told me to come over kneel down and take her cock in my mouth. She said I could stop when I got the entire length down my throat and it was well lubed. That didn’t take long at this point. She told me to insert the egg into her and take off my panties. I reminded them that I still had the plug in and they told me to remove it and place it in the bathroom. I did so and as I set it in the sink, the women walked in behind me. Amy told me to bend over the counter and offer her my pussy. She said she wanted me to watch in the mirror as she lined me up and inserted and took me for the first time as a woman. I could see everyone getting ready to take pictures. Beth fixed my makeup one more time. Then I was told to get in position. My legs were parted slightly, my knees bent slightly and braced against the counter, my heavy breasts hanging down below me in my bra. As I looked I thought how excited I would be if roles were reversed and I was standing behind Amy in this situation. I noticed in the mirror that Beth had the end of the egg control in her hand. Amy placed the head at my entrance, it didn’t feel very wet, I hoped there was enough lube, I was told to look in the mirror and then she pushed it in. Pictures were taken. She gave me time to relax, expand, and then pushed in a little more. She told me I could control this by pushing back as I was ready for more or she could drive in, but she intended for me to take all of it. So I did. Slowly. And once all the way in, Amy grabbed my hips and began thrusting in and out. I breathed heavily and I could see Beth adjust the speed on the egg. After a few minutes, Amy pulled completely out and then back in several times. She then asked if everyone saw what they wanted and then told me we were heading back to the couch. She layed on her side again and had me lay on my side in front of her. She had me role my top leg forward and bend it providing her access to me she told me to place the head of her member at my entrance and as I did she pushed in. Her movement wasn’t as free so the thrusts were shorter and quicker. Everyone watched and I was encouraged to moan and beg for more and explain how thankful I was to be serviced by a big cock. More quickly than I expected Amy came to an orgasm and buried her cock in me. As she came down she told me to hold still as she pulled out. She got up, kissed me on the cheek and thanked me.

Carolyn declared she was next and told me she was ‘fucking me like the slut I was’. She told me to kneel on the floor and she walked in front of me presenting the cock I had already practiced sucking. I lubed it up and she told me to turn around and get on all fours. I did so, I knew doggy style would certainly be in play. She asked me how an experienced woman presents herself. Not understanding the question, she barked out ‘ass up, face down, put your hands out in front of your head palms down’. I did as directed, but it was hard because I didn’t want the weight of my body pushing on my heavy water balloon breasts. So I did my best to support myself somewhat with my elbows while arching my back down. She had me lower my hips down because ‘my pussy was higher up than normal girls’ and to put her cock at the entrance to my pussy. I then had to tell her how much I needed her, wanted her to stick a cock in me. The words were specific to ensure it was a request that feminized and humiliated me. She pushed in quickly and pumped forcefully with long strokes and a consistent rhythm. She held my hips controlling our motion, demanding that I tell her how good it felt, begging her not to stop. It was arousing to be so slutty. My cock felt excited but it wasn’t hard, I think due to her large dildo in me. She stopped thrusting and said since I wanted it so bad, I should start thrusting back. I did so but my motion wasn’t the full length and that was quickly pointed out. I did my job, I continued to beg her for her cock and I know she did everything she could not to orgasm but eventually she did. She stayed in me forever but when she pulled out she told me to turn around and thank her for the great time she gave me.

Beth told Jen to go next. Jen told me to crawl over to her, between her legs, and suck her cock. I did so. My dick was getting semi hard and that was quickly pointed out, that I was excited to suck cock. Jen said I was going to be on top and she climbed out of the chair and laid on the floor. I climbed on top of her. She told me to suck her and then straddle her. I lined myself up and slowly lowered myself on her. It was hard. I tried to squat up and down and bounce but my legs didn’t hold.out very long. Then I rested on my knees and pivoted up and forward then back and down. That worked better. The women told me to rotate my hips more which I did. I was breathing heavy from the work. Beth had the egg on high even though I wasn’t talking much, partly out of mercy for me, but she also wasn’t interested in Jen getting too much attention. My heavy breasts pulled on me with every motion but finally Jen came and I was able to roll off. Exhausted.

After a few minutes, Beth asked me if I had energy for her. The only answer that could be said was yes. She asked me to get cleaned up, fix my makeup and put my panties on. I had a hard time finding those, but I did what she asked. She asked me to sit with her on the couch. It was just her and I even though everyone else was watching. We kissed, she kind of took the lead, she felt my body all over. I explored her naked body as well. While she brushed over my satin panties she didn’t directly acknowledge my penis, even though it was getting stiffer as time went on. As I caressed her she would skillfully push my hand to her strapon. Eventually she coerced me with her hand to lean forward and take her cock in my mouth. I was so into the moment when she reached across me and started to push my panties down. She laid me on my back and pushed my knees apart and lifted them toward my breasts. She positioned herself over me and placed her member to enter me. She slid in and completely filled me. It was erotic and sensual. She moved her hips and thrusted while hovering above me, totally in control. At some point she moved her arms to pin my knees further back and I felt her much deeper. She told me that I could finger myself while she finished. She thrust harder and faster and I began to cum all over myself as she drove one last time into me and had an incredible orgasm.

I felt some sense of satisfaction for bringing her to the orgasm she had. I felt some relief that everyone was taken care of and that this was at a point of completion. Beth kissed me, thanked me and pulled out. She told me to clean myself up, put my panties back on. When I came out of the bathroom, Carolyn was falling asleep on the couch, Jen had her eyes closed on the recliner. Beth told me to wash the toys as she and Amy disappeared with their clothes in hand into the bedroom. As I washed the dildos and placed them in the drying rack, Beth brought some pillows and blankets out and closed the bedroom door. Exhausted, I took the balloons out of my bra and set them on the counter, turned off the lights and laid down on the floor with a pillow and blanket, sore and tired.

I woke up in the morning around 10, Carolyn was walking around and I could hear Beth and Amy talking and giggling. They came out of the bedroom in long t-shirts, no bras. Beth told me to take my teddy off, put the balloons back in and go put a shirt on. So girls night wasn’t over yet. I did as she asked and put on one of my work dress shirts which garnered me many morning after comments from the ladies. Beth asked me to make coffee and french toast. The women sat in the 4 chairs at the table and had breakfast while I was in the kitchen. They talked about their night and made sure to refer to me as some object, prize, score, etc in their conversation. Soon breakfast was over and as I cleaned up our guests got ready to leave.

Beth walked over and reminded me to be thankful for them spending the night with me. Carolyn and Jen were first to leave. As they walked to the door, Beth said goodbye and then looked at me. I said goodbye and thanked them for the evening. Carolyn gave me a kiss on the cheek and said maybe she would call me and we could get together again. She asked me to put my name and number on a piece of paper. I thought she was kidding until she asked again. I grabbed a sticky, thought for a second and then wrote what she asked. She grabbed the paper smiled and giggled and said ‘Thanks Kelly, hope I can make you feel like a woman again’. And they were gone. Amy was ready to leave as well. She said I was sweet and hoped I enjoyed being Kelly. I thanked her and she grabbed her duffle. Beth gave her a long kiss and then she was on her way.

Beth was beside herself with how exciting the night before was. I was tired and I needed a shower. I got my clothes and got into the shower and cleaned myself well. When I was done I dried off and climbed out of the shower. As I went to get dressed, my underwear was gone, replaced with pink panties. Beth stuck her head in and I asked her what was going on and she asked me to just wear the panties through the weekend just to keep the excitement going. She said no one would be able to tell through my clothes. I was a little relieved that she wasn’t going to insist I wear more women’s clothes as I put the pink panties on and they rode over the cheeks of my ass. They were a stretchy fabric and nestled by penis well. A bit of electricity raised through me and then I put shorts on and climbed in bed for a comfortable nap.

When I woke up, I put on jeans and a shirt and joined Beth in the living room. We talked about the previous night, she was still excited by it. She showed me pictures that had been taken, all of which had me in a compromising position. She kept asking if it was exciting for me, and how much I enjoyed it. And as I sat there with panties on under my clothes I told her it was arousing, though I didn’t know how much I would do it again. She pointed out that I had let her use a strapon before and she also pointed out that I was still wearing pink panties so I must find that somewhat arousing. So she concluded for us that we should explore this more going forward in our relationship. I chose not to argue. We went to dinner and the bars nearby and then had amazing sex, and fell asleep early.

I wore panties again on Sunday, green, but on Monday it was back to work and a normal course each day. Thursday evening, Carolyn called Beth. They chatted for a while and at one point Beth put the phone aside and said they were going out this Saturday and asked if I was interested in joining them. ‘Sure’ I said. Beth picked the phone back up and responded ‘yes she will join us!’.

That evening set me on a journey to open a whole different part of my life,and Beth certainly pushed my boundaries over the next couple of years. I have had many new experiences exploring crossdressing as well as my bisexual side. It has made me a better man, and woman…

Source: reddit.com/r/eroticliterature/comments/ri2pdx/how_it_all_started