Dirty Confessions - Reveal your innermost secrets.




I work for a large insurance company and have a fairly responsible job in IT, I am the change manager and enjoy my job, some of the younger girls look up to me and some I am sure despise me, I am 36 and have kept myself in reasonable shape by being an active jogger, I have never found time for long term relationships as I was eager to progress my career. I head up a team of 10 and report directly to the Head of IT, I have no time for petty office politics either.

Every year we have a corporation bash at an out of town hotel / conference center where the managers of all departments gather to hear the company report for the previous 12 months, in all around 200 all descend on this hotel which is block booked by the company, it's a chance to talk and network with old friends from the company.

Anyway the last night of the bash we have a theme night and participation is mandatory, it's a lighthearted way to forget the facts and figures of the previous 2 days. This particular year someone decided to have a 1950's theme night, with a live band playing music from the era, personally I could not have thought of anything worse.

Anyway I was stumped as to what to wear for a 1950's theme, so like all good girls I asked my Mum who would have been growing up into a woman during that era. So I called over and after a cup of tea I told mum of my predicament, I said I was obliged to take part, but did not have a clue as to what to wear.

After a few minutes, mum got up and beckoned my to follow her to her walk in wardrobe adjacent to her and dad's master bedroom, this was like the inner sanctum and all manner of dresses, shoes, jackets and coats were neatly hung or placed on racks. Mum started to select a few items, she had kept every piece of clothing she ever worn, bought, borrowed or was given as presents. She gave me the items and told me to try them on, so I took the items of clothing to the en suit bathroom and undressed down to my underwear, I tried on a dress with such a slim waist and large top half, I could not fit and it didn't look very appealing, as I was going to throw myself into the night I wanted to look glamorous and above all sexy.

I walked out to mum and said it just didn't do anything for me. She looked and was gone for a few minutes, when she returned she handed me a bundle of items and said if you need a hand call me. I walked back the bathroom and looked at what she had given me. They were not outer wear clothes they were genuine 1950's lingerie. I stripped off my bra and panties, where to start, the dress required a super slim waist, so I called for mum to give me a hand, I was still naked when she entered the bathroom, "when did you start shaving down there?" was the first thing she said, always matter of fact was mum, I ignored her question and asked where do I start? Well she picked out what she called a waspie with the longest suspenders I had ever seen, she fastened this around my waist and pulled it super tight, I felt it pull in my waist.

She then selected a bra, which looked like it had to motorway cones instead of cups and I put it on, my breasts looked very impressive but conical, she then suggested I try the dress on, wow what a difference, it fit me like a glove, very slim tiny waist and a very large bust, I had a look in the full length mirror and was delighted with the result. Mum then suggested I wear grey stockings, seamed of course and a pair of panties from that era, they were white silk loose legged with very strong elastic around the waist, they were not snug and when they were on, I could feel my bottom was free to jiggle and move.

So I was sorted, mum even supplied makeup from that era, very red lipstick, and said I should wear my hair up.

I drove to the hotel on the morning the conference kicked off, parked my car and checked in, we all had single rooms except for a few of the juniors who had to share. The conference started with lots of boring speeches and an awful lot of facts and figures, the 2 days dragged and it was the same thing every night, married men, single men, married women and single women all trying to hit on someone who was in a slightly higher post than themselves. I enjoyed a bit of banter with the other IT guys and girls and spent my evenings propped up in the bar.

The conference ended at 5 pm and we were all requested to be back in the ballroom for 9.15 sharp for the end of conference bash. So without further ado I made my way to my room and took a long hot bath, I made time to make sure I was clean shaven down below and relaxed with a glass of wine.

After my bath, i climbed from the tub and wrapped a robe around my naked body, I dried off and took my 1950's attire from my case. Now how did this go I thought to myself? First the waspie and I had problems pulling it tight, it was a two person operation, I slipped on the robe and went next door to one of the girls from IT, I explained my situation and she readily agreed to assist me. She was getting ready also, but was almost fully clothed, I opened my robe as modestly as possible and she pulled the waspie tight. I thanked her and left.

Next item when I got back to my room, oh yes stockings attached to the suspenders, seams straight, then the bra I was starting to look like a pin up from the 1950's. I found the white silk panties and pulled them on, they felt different to my normal huggy one's as these allowed for my bottom to move and I could only imagine how my bottom would jiggle on the dance floor! Then the crowning glory the dress slipped on and I must admit I looked pretty hot, small waist, large bust, round voluptuous bottom. I fixed my hair and make up and was ready to make an entrance at 9.15 on the dot!

The ballroom was almost full when I got there, some employees and managers had made more of an effort than others, however when I walked in, all eyes were transfixed on my bust! I was enjoying the moment and even some of the girls who probably despised me, were actually giving me compliments. The evening was a huge success, great music from the era, a free bar and a decent enough meal. I was up on the dance floor shaking my bottom in my white silk panties that only I knew I had on. At the end of the evening the band played a slow set. I was just about to head to the bar when one of the retired directors asked me to dance, well this chap was in his 70's and was dressed as a Teddy Boy.

We danced and as it was a slow one he held me tight. We was making small talk about what department I worked in and stuff like that. As we danced I felt his hand drop to my bottom, I didn't mind, he then asked "are you wearing stockings?" I replied "Yes of course it's a 1950's night". He then said "can I see them?" well of course he could not see them on the dance floor, so I felt pretty safe as he was in his 70's and told him my room number and to call for a drink. I made my excuses to my colleagues and retired for the night, I was in my room and within 10 minutes I heard a knock, sure enough the old gent had called to my room.

He apologized for asking to see my stockings, but he had watched me all night dancing and was enthralled with my jigglerly bottom! I laughed and offered him a drink. We chatted for a while and then I said it was getting late and if he was going to get a look at my stocking tops I had better show him soon. With that I stood and lifted the hem of my dress up over the tops of my stockings, he saw what he wanted to see, the smile on his face was priceless, he then asked "how are you keeping them up?" so I said, "no touching" and took the dress off. He looked and asked me to turn round in a circle, which I did.

He looked at me and smiled and said "thank you, you have made me very happy." I don't know if it were the drink or the fact that I was sure this old gent was not going to try anything on, so what I did next was spur of the moment. I unhooked my stockings and pulled them off, I asked him to assist with the removal of the waspie and bra, his hands were trembling, soon I was standing in only my white silk knickers given to me by my mum. I asked him "would you like to touch my breasts?" He said nothing, but reached out and gently fondled and caressed my breasts. I was single and what harm if I was bringing some happiness to this old gent? He moved one hand down to my white silk pantie covered bum and fondled and kneaded it. Very slowly his hand moved quite easily into my panties via the loose leg fitting, so this is why mum wears them? I said "you can take them off if you want to" which he nodded to and quite easily started to remove them until I was naked. I could hear his breathing getting deeper and I could feel his hand trembling.

I asked him "are you happy now?" to which he replied "happier than I have been in a long time." I was feeling empowered I was single, naked and making an old gent very happy. I became bolder and asked if I could see his cock, he said " I am old and I have not had an erection in 7 years". I undid the buttons of his fly and put my hand into his underpants and fished out a limp 7 inch penis. I gently squeezed it. He was still caressing my breasts and bottom, he appeared to have no interest in my shaven pussy? I undressed the old gent, his body was in very good condition, still muscular and firm which surprised me. Once he was naked I laid him on the bed and took his flaccid penis in my mouth. I could feel it was having the desired effect and his penis was getting erect.

I mounted him and rode his cock slowly. He was busy with my boobs and bottom and I made sure to get as much depth as possible. By now I was getting very aroused and must admit that the old gent fucked me to a climax. I do not know whether or not he came as I was so wet.

We kissed and I got off him, He said "can I have you white silk panties?" I said they were a present from my mother, not my usual knickers, but from now on they will be. I relented and gave them to him. I never asked his name, however a couple of weeks later I called to mum and she asked me with a little glint in her eye how the conference went, I said "it went well" to which she produced the little silk panties I had given to the old gent? Apparently he knew mum in more ways than one and had returned the panties as he wanted to see her in them as well! She obliged him and I laughed to myself as he had fucked us both.