The week started off like any other week with one difference. I couldn't wait to finish work and go clothes shopping!
Now being a typical guy, I hate any kind of shopping as a rule but this was different.
I felt I had to buy some sexy designer underwear. Most of my boxers were pretty boring and mostly black. Now I think about it, all my boxers were black.
Time to get something bright, bold and skimpy? This was new territory for me. I usually buy plain, comfortable boring boxers. Well, all my clothes are plain, comfortable and boring!
5pm couldn't come soon enough but when it did, I found myself jumping in my car and heading to the shopping centre.
Being a Monday it wasn't too busy in the car park and I easily found a space, got my ticket and headed inside.
Now where do I go? I avoided the big stores and found myself in a small menswear store. They didn't seem to have much in the way of underwear, just a couple of shelves with a variety of coloured boxers.
Apart from the colours, they still seemed a bit boring so I left empty handed.
I don't know if you've ever tried to shop for sexy boxer shorts on the high street but, believe me it's not easy.
I must have visited every shop there and had almost resigned myself to wearing a pair of my plain old boring black ones I'd had for years. Then I took a chance and walked into a big supermarket that had a clothing section upstairs.
Here we are. Right at the back of the shop. A few pairs of what looked and felt like silk boxers. Nothing particularly revealing, just red and black silky boxers. I grabbed a couple of pairs, paid at the checkout and walked briskly back to my car feeling very pleased with myself.
30 minutes later I was sitting in my front room, feet up wearing only a pair of my new sexy, silky boxers with a stiff one in my hand (a glass of brandy).
Now I know why women love silk lingerie. My cock was throbbing as soon as I put the boxers on.
I reached for my phone and took a couple of photo's of my now tented boxers and sent them to my new friend for her approval.
I got a message back a couple of minutes later saying 'very nice, will have to see what they look like on the night xx Jill.'
It had never even crossed my mind that I didn't know her name, but was arranging to serve her and her friends with next to nothing on.
Funny how names don't seem important when your cock rules your head!
I'd best get these boxers off then or I'll be shooting my load in them the way they feel on me. I didn't bother getting dressed, I just sat down at my laptop and started surfing for porn.
I soon found a nice CFNM website and started reading the stories.
I was cuming like a horse in no time and decided to clean up and go for a shower.
The next few days and nights were pretty uneventful with just a couple of messages going back and forth. Jill kept checking to see if I was really going to go through with my serving duties for her and her friends.
I must admit that as the week went on I started to have second thoughts but Jill knew just how to keep me interested with her encouraging texts.
Saturday soon came around and Jill sent me an early morning text with her address and a time to be there for.
My heart was pounding as I read it and all I could think of texting back was ok.
A text came back 'Don't let me down tonight, the girls are really looking forward to this.' I swallowed hard and sent back 'Don't worry, I'll be there as promised.'
The day went far too quickly for my liking and as I stepped out of the shower and dried myself off, I wondered if I really wanted to do this.
I didn't put my new boxers on as I thought it best if I got changed there, so folded them up and put them in my pocket.
The time was 7:15. Be there for 8 Jill said and it was a half an hour drive so I set off.
I reached her house at 7:45 parked at the side of the garage, like Jill had instructed and sat open mouthed at the sheer size of this place. This wasn't a house, it was a mansion.
Still time to back out but my cock had other ideas as it twitched at the thought of wearing my sexy silky boxers all night.
I jumped out of my car and rang the doorbell.
As the door opened Jill greeted me with a hug and a kiss on the cheek. I took a moment to check her out and I wasn't disappointed. She looked very nice in person and she had a body to die for. Her dress was tight and clung to her ample curves. I say ample but I mean ample in all the right places and showing a nice bit of cleavage.
I stepped inside and she closed the door behind me.
She led the way to the lounge and asked me to sit down next to her.
"I wasn't sure if you would come or not," she said. I told her I'd had second thoughts but curiosity got the better of me and so here I was.
"Well I think we had better lay down a few rules if we're all going to make the most of this evening," she said.
I thought, how many rules could there be? I'm serving dinner to a couple of women in my boxers.
"Right, first and foremost you must do what I ask of you.
Second, refer to myself and my guests as ma'am.
Third, I or my guests might get a little frisky as the evening goes on. We may get a bit touchy feely if you know what I mean." I just sat there nodding my head. "On no account must you pull away or pull our hands away, understand?'
I just nodded again.
"I think you mean to say, yes ma'am" she said and I found myself repeating the words after her.
"Time to get changed, you can do that here" I just looked blankly at her. "Quickly," she said "My guests will be arriving in 15 minutes and you are to greet them at the door."
I folded my clothes in a neat pile as I took them off, then slid my old black boxers off as Jill watched. She handed me an apron, picked up my pile of clothes and carried them away. "Excuse me ma'am, my silk boxers are in my trouser pocket," I said. Jill just raised a hand and waved it saying "Oh, I don't think you will be needing those" and walked off with my clothes.
I put the apron on and it just about covered all the important parts apart from my bum. I was feeling very exposed as I tied a bow around the small of my back.
Jill came back and had me spin around for her. She complimented me on keeping in shape and said she particularly like the shape of my bum.
Ding Dong!
"Hurry now and show my guests into the lounge, don't forget to address them as ma'am and offer them a drink from the bar in the corner."
"Yes ma'am" I said as I went to answer the door.
I opened the door and there stood two ladies, I'd guess in their mid sixties. One a bit tubby in a long flowing skirt and button up blouse. The other very slim wearing a light white cotton dress buttoned from top to bottom, almost to her ankles.
"Good evening ladies, please step inside." The slim lady giggled and the tubby lady just looked at me and tutted!
As it was a warm evening, neither wore a coat and I found my eyes being drawn to the slim lady's nipples and I could tell she wasn't wearing a bra. My cock twitched as I ogled her. She definitely caught me and smiled as she walked past me.
Tubby was wearing a bra as there was no way she could just rely on gravity to hold those melons up! She caught me looking too and shot me an icy stare!
They both wandered through to the lounge as I closed the front door and followed.
"May I offer you both a drink?" I asked.
Slim asked for a red wine and Tubby asked for white. As I walked past them to the bar I heard a gasp, then a bit of whispering as they caught sight of my bare bum.
I poured the drinks and served them on a tray as the doorbell rang again.
Ding Dong!
I walked out of the lounge and into the hall to answer the door again.
I opened the door to another two women, very pretty looking, probably mid fifties and twins! I bet they broke a few hearts between them in the past.
Both slim but curvy. One in a red mid thigh length dress, the other matching but in black. All I could think of was Wow!
"Good evening ladies," I said just about audibly. "Please do come in."
They both made their way to the lounge hips swaying so sexily. My cock was starting to get very interested!
I followed those two swaying hips to the lounge and was caught by Tubby again and got the icy stare for the second time in less than 10 minutes.
"May I offer you both a drink?"
"Vodka and Tonic please," the twins said in unison so I turned and walked towards the bar. I could hear even more whispering now and I felt my face flush as I brought these two pretty twins their drinks.
At that moment, Jill walked in and greeted her friends with a hug and peck on both cheeks.
"This is Joe, our servant for this evening, Joe, this is Tracy (Tubby), Susan (Slim), Jane and June (the twins)."
"So what do you think girls?" Jill said as she walked towards me.
The twins looked me up and down, smiled and said "very nice." Susan smiled and winked at me. Tracy, well she just gave me that icy stare!
"I'll have a white wine please Joe," Jill said to me. As I turned towards the bar I felt a hard slap on my bum. "Didn't you forget to say something Joe?" "Sorry ma'am, yes ma'am," I said as I hurried off to get her drink to the sound of all five women giggling.