Jessica's Story

*** This story is based on real life. Names and locations of the main characters are real. Everything that takes place within the story has not necessarily happened; but is loosely based on fact. ***

My story is bizarre to say the least but I wanted to share it with you all. My name is Jessica and I have been married to Rob since 1997. I am a marketing manager for a large retail chain and he is an engineer. We live in the town of Farmington in Michigan. Rob would be so embarrassed if he knew I was writing this story. You see Rob has a secret that he keeps from everyone but me, something that would drive him insane if he thought that anyone else knew about it. Rob has a fetish for dressing up in women's clothes. In the week under his suit he wears women's silk thongs or cotton panties to work, and on the weekend he has several outfits that he likes to wear including a rather sexy little maid's outfit and a elegant ball gown.

Ever since I discovered Rob's perversion I have been the one who has 'worn the trousers' in the marriage. He does what I tell him or he is punished. Only I am allowed to initiate sex, which happens maybe once a week, in which he is very lucky to cum. If he is good he might get a blowjob or maybe a hand job. If he is very good or if I feel like it he might get to fuck me but nothing much more. I have always found it difficult with Rob, he is not a very good lover and I have always needed something extra to get me off.

Because of Rob’s inadequacies in the bedroom I often get dressed up, put on my sexiest underwear, hold up stockings, highest heels, tightest most revealing dress and leave Rob in the house as I go out on the town. It drives him wild with jealousy but he would always be too much of a sissy to challenge me. Several times I have brought men home. Rob is sent into the spare room while these real men fulfill my sexual needs in ways he could never do.

This is an account is of one such evening.

I had been feeling horny all week, I would only sit down for a minute and my mind would drift. Often in meetings I would loose track completely of what the discussion was and only be brought back to earth with the sound of someone saying my name. As my name was repeated and I regained consciousness my mouth would dry up and my mind would race trying to figure out who had asked me what and how best to answer it. I am good at my job and it didn’t take much for me to catch up with the conversation once I'd lost it; besides these meetings were almost always about the same things anyway.

On this day my daydreaming was especially vivid, they focused on a colleague of mine, a man called Frank Bauer. Frank was a little older than I was, he had broad shoulders and a good body; I mean even through his shirt you could tell he worked out. He was tall with dark hair; very dark eyes and he spoke with a firm but compromising tone that made you sit up and take notice. I had often looked at him and compared him to Rob. There wasn't really much of a comparison to make; Rob a sissy boy with a little cock and no bedroom skills whatsoever or this 'man mountain' who got me wet just by talking to me. I had often fantasised about Frank but had never dared to make a move on him, he knew I was married so he probably thought I was off limits anyway.

Today had been a busy day and I'd had a succession of meetings, which meant I couldn't actually get any work done. So at seven o'clock I was still sat in my office ploughing through some paperwork. I had phoned Rob to tell him I would be late and told him to get the diner ready and also that the house could do with a clean before I got home. He of course had agreed and had set of to do the chores. Most of the other people had left and it was very quiet so I managed to get a lot done. At about five to eight, I stopped working and closed down my computer, I hadn't finished it all yet but I figured it could wait until Monday. I picked up my case and coat and opened my office door; I then reached back inside to turn the light switch off. As I closed my office door I looked up to see Frank walking down the corridor towards me.

We chatted as we walked out of the offices and got into the elevator that would take us down to the parking garage. I put my finger out to press the button and noticed that I had left my wedding ring in the office. As the doors closed I cursed, my fingers felt strange with out it. Frank looked concerned and asked what was wrong; I told him that I had forgotten my wedding ring. He assured me that it would be all right in my office over the weekend, however if I wanted to go back and retrieve it he was happy to escort me. I thought about it and told him not to worry, Rob wouldn't even notice if I weren't wearing it. Frank looked surprised, I explained that Rob was a waste of space and not what I needed in a husband. As I looked down at my feet wondering if I had gone too far, Frank coughed and asked if maybe he could take me out sometime, to try and cheer me up, as friends he added on the end for measure. I smiled coyly and looked up at him, explained I'd love to and arranged for him to pick me up tomorrow night at eight.

I got home at about eight thirty and parked my car behind Rob's Durango. I grabbed my case and made my way to the door, pushing it open and stepping in. I called out for Rob and heard him scurrying about upstairs. He walked down the stairs towards me wearing his maid's outfit, complete with hold-up stockings and frilly panties that were both clearly visible under the frilly skirts, headscarf and feather duster. He bowed his head as he approached me, he still got embarrassed about dressing this way and his cheeks flushed red showing it. I asked if my dinner was ready handing him my case and coat, he led me into the dining room and sat with me while I ate. That night I sat and relaxed while watching television while Rob spent most of the time dusting and vacuuming around me still dressed up like a fairy. At one point I told him to go do the upstairs as the sight of his little cock bulging in his tight panties turned my stomach. I was sleepy about eleven o'clock and decided to go to sleep, I went up to our bedroom and stepped out of my day clothes and put on one of my silk nighties. I then brushed my hair and teeth and washed before climbing into bed. I was very tired so as soon as my head touched the pillow I was fast asleep.

I slept soundly that night and woke up the next morning with an arm wrapped around my waist. It felt nice being there, quite manly, I ran my hand up his arm and then stopped once I felt the silk of Rob's nightie. I then pushed him off me as the realisation of it all hit me. I lay there thinking about the day ahead, I was going out with Frank tonight and there was shopping to be done. The thought of it was making my pussy wet and I couldn't help run my fingers down over my breasts and between my legs to stroke my clit. I rolled onto my back and saw that Rob was lying on his back next to me. I pulled the covers off him and sat up looking down at him dressed in a soft blue silk nightie. He looked ridiculous with his stubble, hairy chest and nightie; I lifted his nightie up and looked sadly at his hard cock. I took it in my hand and stroked it up and down trying to make it grow some more but nothing happened except put a smile on his face. My fingers were still down between my legs and they were getting slick with my juices. I straddled Rob around the shoulders with my knees holding his arms down; I then lowered my pussy to his lips and told him to lick me. He was useless at this too but I had learnt how to grind my hips against his face to make myself cum rather than to rely on his to do it for me. As his tongue lashed around aimlessly I rubbed my clit against his nose and rode his mouth, forcing my pussy down on him, making him lick and suck me until I came. I climbed off and lay back on the bed a little short of breath, but not nearly satisfied. I got up glanced over at Rob who lay there with his cock in the air and made my way to the bathroom.

I got washed and dressed, picked up my bag and walked out of the house. Rob looked out of the window after me, I hadn't told him where I was going but I hardly ever did these days. I climbed into the car and made my way into the main shopping part of town. I wanted something special to wear tonight, something that would turn Frank on, something that would make him want to bend me over and fuck me the moment that he saw me. I needed that. I walked into the mall and went to one of my favourite shops it was called Dragonia's. In it they had some amazing dresses, they were sexy but not too slutty, real head-turners. I had bought several dresses here before and every time I had worn them out it was impossible not to feel like the centre of attention. I walked in and was greeted by a young Chinese girl called Ling whom I had met on previous visits; she recognised me and asked how I was. I was made to feel at ease as Ling led me around to the shopping area, sat me in a chair and then offered to get me a glass of wine. It was nice to sit and be waited on. The shop was very lavishly decorated with gold leaf and red velvet over the walls.

The main area of the shop was made up of a large room with four changing rooms to one side, a large mirror against the front wall and a couple of doors in the other wall. Ling wandered back and handed me a glass of red wine. We then chatted for a while about what exactly I wanted and how I imagined my dress would look. She asked me to wait as she took her notes and wandered off through the door. I sat for about ten minutes sipping my wine and flicking through a fashion magazine that was on the table next to me. Ling returned and looked excited; she always seemed to get excited about showing off clothes. Ling sat in the chair next to me and clapped her hands together, she leaned over to me and whispered that she knew I'd love one of these and then turned back to watch the show. The left hand door opened and out walked a gorgeous blonde girl wearing a stunning black dress, that had quite a low cut front and a slit right up the leg that stopped just in time to preserve the wearer's modesty.

The dress hung about three inches off the floor, only due to the fact that the girl was wearing some sexy six-inch heels. She walked around showing the dress off to me. She then slid her leg out from the slit in the dress and let me catch a glimpse of stocking top before stepping back down, turning once more and making her way out of the right hand door. I saw about three other dresses after that one but none of them compared to that first and it wasn't long before I was leaving the shop with the dress, stockings and shoes in a bag. While I was in the mall I also stopped by the beauty salon and had my hair, nails and a very painful bikini wax done, all in preparation for the big night.

I got home about five and Rob was waiting for me, he was wearing his mini skirt and silk blouse and looked absurd. I told him so before walking up the stairs and running a bath. I soaked in the bath for about half and hour being careful not to get my nails or hair messed up. I then got out dried myself and went to get dressed. I unpacked my purchases and laid them out on the bed. I went over to my panty draw and picked out a very small pair of lace panties, which I slipped into. I also picked out the matching bra that pushed my breasts up and together showing off my perfect cleavage. Next were the stockings, I slid them on liking the feel of the lace tops on my thighs. I then checked my hair and applied my make-up. Lastly I stepped into my dress and zipped it up in the back before slipping on my new shoes. They were a little higher than I was used to but I could still walk elegantly in them. I practised, floating up and down the hall. It was a warm night so I didn’t take a jacket and at five minutes past eight there was a knock at the door. I walked down the stairs, and into the lounge to see Rob. He was sat watching the hockey in his skirt and blouse. I told him not to wait up, to which his head swung round to watch me as I walked out of the room and towards the door. Before I opened the door he was behind me in the corridor frantically asking me where I was going and whom I was going with. I told him to go back into the lounge and that I would see him later. He did as he was told, I could see the ferocious jealously in his eyes as his head dropped and slouched back into the lounge.

Frank took me to a very posh restaurant and I thoroughly enjoyed myself as we drank wine and ate exquisite food. I flirted with him and he flirted back, it was obvious that he liked my dress and even commented on how sexy I looked. At about eleven o'clock we were ready to leave, Frank paid the bill and escorted me to his car. He parked up outside my house, came round the car and opened the door for me. I remember commenting on how chivalrous he was being. He walked me up to the door and kissed me on the cheek, I thanked him for a lovely evening and asked if he would like to come in for a coffee. He looked hesitant and asked about my husband. I told him not to worry about Rob before opening the door and pulling him in after me.

Once I had closed the door I pulled Frank close to me and kissed him and he kissed me back, I could still taste the wine on his lips. I felt his hands trace down my back and came to rest on my hips, big manly hands. As we kissed I noticed out of the corner of my eye, Rob was stood in the doorway to the lounge watching as a strange man kissed his wife. I just winked at him and kissed Frank with a little more passion. Once we had finished I took Frank's hand and let him towards the lounge; I told him that there was someone I wanted him to meet. As we entered the lounge I scanned the room and saw Rob sat cross-legged on the far sofa. Frank this is my husband Rob. Frank looked embarrassed. Rob looked angry. Frank then noticed what Rob was wearing and couldn't help a smile breaking up his face. Rob's anger quickly dissipated as the humiliation of Frank seeing him like this took a hold of him. I explained to Frank that this was why I needed a real man to take me out and treat me like a woman because my husband was not a real man.

I took Frank's hand and led him upstairs and to the bedroom. I seductively undid his tie and ran it through my fingers as I found the zip on the back of my dress letting it fall off my body. Frank started to kiss my neck and worked his way down to my shoulders and across my breasts. His hands ran over my waist and my hips, down over my butt and legs. I opened my eyes as Frank was kissing me to see Rob peering tentatively round the door. I lay down on the bed and undid my bra before taking Franks tie and holding my arms up against the bedposts and telling him to tie me up. I knew this was one of Rob's fantasies, but I would never let him tie me up. Rob tied my wrists together and then tied them to the headboard. He then took off his jacket and shirt before kissing me passionately from my lips all the way down past my breasts and onto my stomach. He then jumped down to my toes, kissing them softly and working this way up to my thighs. This attention was driving me wild; my hips were bucking with every touch and kiss. I could see Rob stood there watching everything that was going on. Frank was kissing up into my thighs he kissed softly over my panties, I could feel his hot breath on my pussy and it was making me wet. He took both hands and slowly lowered my little lace panties exposing my recently waxed pussy. As he took the panties in his hand he also noticed Rob stood in the doorway, he beckoned for him to come in before throwing my panties at him and telling him to sit in the chair and watch how a real man fucks his wife. It was a lot for me to take, I had brought men home before but they had never invited Rob in to watch, my body shuddered as Frank touched me once again. He eased my stocking clad legs apart exposing my wet pussy to him then sinking down he started to lick and suck my clit, making my whole body shake and convulse as his tongue and lips drove me wild. I could feel his warm breath on my skin and his big hands cupping my butt as he brought me to orgasm and oh how I had needed it. I screamed out as waves of pleasure ran over my body, the sensation of being restrained also turned me on thinking he could do anything he wanted with me and I was powerless to stop him. I looked down at Rob, I must have looked a sight, tied to the bed making faces as I came, he just watched without blinking. I licked my lips before resting my head back on the bed.

Frank must have then stripped naked because the next sight I had was of a large cock coming towards my mouth. I opened wide and took it all in as best I could, Frank started to pump in and out of my mouth like it was a pussy. His hands ran over my breasts as I sucked, tasting the saltiness of his pre-cum on his cock. I could see Rob watching as this cock that was more than twice the length of his slid effortlessly in and out of my mouth. Frank decided that it was time to go further so he withdrew his cock from my mouth and positioned himself between my legs. I felt him pressing against my pussy entrance and he very slowly eased himself inside, I wasn't used to having such a big cock in me so it took some effort on his part to squeeze into my tight pussy. But once he was in it felt wonderful, the sensation of actually being stretched felt great and as he pumped his cock in and out of me I couldn't help but scream out every time he thrust in. He lifted my legs up over his shoulders so that he could penetrate me deeper, by now I would have done anything for him.

Rob sat in the corner of the room didn't even enter my mind as long as this man had his cock in me. He would thrust in and then hold it before pulling out nearly all the way before thrusting in again. I came again as he pumped into me. I feared at one point that I would pass out as he squeezed my breasts and fucked my pussy. My hands were still tied up to the bed and Frank decided to release them. I ran my hands over his arms and shoulders feeling those manly arms grip hold of my breasts. I ran my nails down his back and gripped his butt as he thrust in and out of me. I could feel Frank's cock growing in size and could tell that he was about to cum. I felt the warmth in my pussy as his cum squirted deep inside of me. He collapsed down on me panting as he emptied himself in me. He slid his deflating cock out of me and lay on his back next to me catching his breath. Rob watched on his eyes were as big as ever and I could see that his little cock was hard through his silk thong that was clearly visible. I could feel cum slowly seeping out of my pussy and had an idea.

I closed my legs tight and called Rob to come lie on the bed next to me. He looked like a startled rabbit caught in the headlights but once I asked him again he agreed and lay next to me. I kneeled next to him and then straddled his face pushing my pussy down onto his lips. He struggled a bit but I held him in place with my knees. I felt his tongue enter my stretched pussy as a squeezed my pussy muscles forcing cum out of me and into his open mouth. I remember telling him that if you are going to dress like a girl you'd better learn to drink cum like a girl. I came as I ground my clit against his face and collapsed back onto the bed between Rob and Frank. The last display had turned Frank on again and it wasn't long before he had me on my hands and knees and was fucking me from behind. I had sent Rob into the spare room so he wouldn't disturb us although we probably kept him up all night with my screaming and moaning.

In the morning Rob brought us breakfast in bed dressed perfectly in his maid's outfit. He had even bought some new high-heeled shoes to go with it. I complimented him on the shoes, he didn’t reply just blushed. As he gave me a cup of coffee I thanked him and patted him on the bum before he walked out carefully, leaving Frank and I to wake up on our own.