Little Bo Peep - The First Outing

Nobody warned me that my days would be turned on their head from this day forward. Our relationship was what you could consider "normal". We enjoyed our ventures out to the pub, to cosy nights in with nothing but a movie and a blanket to keep us warm. While we both had our moments of living on the wild side when it came to set it was all pretty normal there too. Janice had recently turned 28 while I was fast approaching 30.

She was slim but, as they say, had curves in all the right places. Her breasts were wonderful fleshy handfuls of delight which still made me gape each and every morning or evening when she was changing into her clothes for the day. I would find myself staring when she would dash between the bedroom and the bathroom on the occasions that I would work from home at her body distracted me from whatever boring spreadsheet I would be focused on at the time. Her ass was nicely round and she had hips that I loved to hold on to. As far as I went. I had always been tall and slim with a package that Janice would swear was getting thicker each time she saw it. Although, this was just to bolster my confidence I'm sure. My hair was starting to thin a little bit but I still had enough to warrant regular trips to the barbers to keep it from becoming long and messy. At the moment it was nearly at my shoulders and from all the time I was spending out of the office.

It was the middle of October when I found myself at my home desk when Janice arriving in the door from work and kicking off her shoes by the door.

'Hey, Tiger' she called out.

The nickname 'Tiger' came from the fact that I had a pretty wild time when we met in University and also from the fact that my real name was a plain and simple Tom so she liked to spruce it up by calling me Tiger. My mother drunkenly admitting that it was from their love of Tom and Jerry when my sister was born that put the idea of Tom in their heads.

'Hey Jan' I replied back, 'I'm in my office'.

She arrived in the doorway a few seconds later and I could see she was laden with bags from a shopping trip after work it seemed. Shopping was a love of hers so I couldn't help but smirk.

'Guess your day went well then?' I enquired. 'Judging by all the bags it looks like it!'

A sly smile curled up the corner of her mouth.

'You have no idea!'

It was then she unloaded all the stories she had and the people she'd seen while out while at the same time showing me some of the practical things she had bought. In classic Janice fashion there were some not-so-practical things in her bags too as there were "just on sale".

She then reminded me that we were heading to a co-workers Halloween party in two weeks and had picked me up a costume to wear while she had also gotten one for herself. I wasn't allowed know what either of them were until the day of the party but she told me that I wouldn't be disappointed. 'Siobhan and Mark have sent over the details and it seems like the party is going to be a big deal. They've pulled out all the stops with decoration this year.'

'And there is no way I can leave early from this one is there?' I queried, knowing full well I was in this one for the whole night!

'No way!' exclaimed Jan 'You'll enjoy this one, I promise. Plus they said we could stay the night so we don't have to fight with everyone else for a taxi at the end of the night'

I didn't know her co-workers too well and their nights always ended up being good fun but Jan knew that I wasn't the full on party guy that I was when we were in University together. Saying that, neither was she. We were always more than happy to be the ones on the couch towards the end of the night and more often than not leaving early as we got tired.

Jan closed the gap to me in my chair and half straddled me. She brought her lips to my ear and whispered.

'As I said, you're not be disappointed this year.'

She skipped out of the room scooping up her bags leaving my mind wandering to what exactly she was planning or had planned for this party.

It wasn't long before the day of the party arrived and we both awoke quite early. I made us some bacon for breakfast and after we cleaned up I hopped into the shower. As I was washing my hair I heard Jan enter where she slipped the shower door open and joined me. We would often have showers like this, sometimes saving time, other times just so we could explore each other's bodies before some fun in the bedroom. This was one of those times where she slipped her hands around my waist and down to my semi-erect cock. I groaned as her fingers wrapped around my member that was now getting stiffer and stiffer as I felt her breasts press into my back while her lips danced around the base of my neck.

'I can't wait for you to see what we're going to be wearing tonight', she sighed between kisses.

With some concentration I mustered, 'Oh yeah?'

'Yeah... you're going to... really... have some fun with it.'

As I felt and orgasm building, Jan was running her free hand over my ass while and slipping into my well cleaned crack with teasing fingers. However, with a playful slap she let go of my cock and turned me around.

'I want to save this for later so go get dried up'

Begrudgingly and against my own wishes of what I wanted to do to her right now I left her to finish in the shower while I towelled off.

'By the way,' she said from under the shower head 'your outfit is already laid out on our bed for you. I hope you like it.'

A moan escaped the shower cubical and I could see her shadow of her hand between her legs. I fought the urge to hop back in with her and as if reading my mind she said,

'Don't worry. I'm only teasing myself too. We'll continue this later.'

Walking out from the bathroom to the bedroom the chilly air cleared my head a little although it did little to dampen the raging erection that I now had. On the bed was a small package and box next to it with a note on top.

'Get dressed, officer. I'll promise I'll be a good girl for you tonight. Little Jan Peep x'

'Little Jan Peep,' I spoke to myself and chuckled.

I opened the package and inside was a very realistic Police uniform. It included black tight boxers, pants, shirt and a Police vest to go over the top. If I didn't know any better I'd have though it was real. Next to it in the box was a pair of handcuffs and an extendable baton. If her note was literal and she was going as Little Bo Peep and I was to be her Policeman for the night then maybe the night wasn't going to be too bad after all. As I heard the shower being turned off I picked up the boxers and was about to slide them on when I noticed the size. Small. I was a pretty thin person but there was no way I was fitting into a small pair of boxers. Current boner situation aside.

'Uh, Jan,' I began, 'I think there has been a mix-up at the shop.'

'Umm ... Tiger...' Jan walked into the room holding up her outfit which looked as if it could swallow her body.

We both laughed and I sat down on the bed. 'Well I guess I could just dig out the old outfits from last year'

'You could, except those were part of the boxes of clothes that got ruined when the pipe burst, remember?' Jan reminded me.

'Ah shit, yes...'

We looked at each other trying to come up with a plan. Jan was first to speak.

'It looks like they just confused our sizes. I gave them a form with our sizes for the outfits but I they have put them the wrong way around, as this would definitely fit me.' She held up the boxers that were on the bed and held them up to her waist.

It slowly dawned on me where she was going with this.

'No. No way. I'm not wearing a dress.'

'But Tiger, baby! It's not THAT bad. You could defiantly pull it off. Imagine. You could be a sexy tall Little Bo peep... and for one night only I'll be the sexy Policewoman.'

'Not a chance.' I said.

Jan knew she had a knack of always getting what she wanted. She was standing naked in front of me and twirled around and bent over while slipping the boxers she was still holding up her legs. They hugged her ass perfectly as she stood upright again. Despite my best efforts a little groan escaped from me as she turned to face me again.

'Well? What do you think?' she questioned.

'You're the worst. You know they look amazing on you.'

She smirked wickedly and turned around again. She disappeared from the room and came back shortly later with the rest of the items for the Bo Peep costume. On the bed she placed a pair of stockings, a little hat and a lacy pair of underwear which didn't leave a whole lot to the imagination.

'Besides,' she said 'not many people will recognise you anyway since your hair has gotten longer.'

Just as she had done with the boxers she held them up in front of her and wiggled her hips.

'Can't I just skip the party?' I questioned, 'I won't be missed and you can still wear your costume as it's not inappropriate.'

Jan laughed and sighed at the same time.

'Don't be silly Tiger, you can pull it off and I know that I'll definitely miss you if you're not there.'

'Fine. I'll wear the costume but there is no way I'm wearing these' as I reluctantly pulled the panties from her hand.

'Imagine how much people will stare if they can see your ugly man boxers instead of these. Plus, I think it would be super sexy to see you in them,' Jan giggled.

Knowing that I was fighting a losing battle and Jan swaying in the ass hugging boxers in front of me I could do nothing but give in which resulted in squeals of delight from my wife. She came closer to me and planted a deep kiss on my lips.

'Maybe if you let me shave your legs this will all feel even better as they slip up your legs', she nodded at the panties and stockings now on the bed.

Unsure as to how I agreed we found ourselves back in the bathroom with Jan skipping around like a schoolgirl fetching a fresh razor and lather. Minutes later my legs were as smooth as I have ever felt them. With a wry smile she caressed my once again stiff member and muttered that it should all be tidy while we're at it. When she stood back to admire her work I was smooth between my ass cheeks, my cock which now stood extremely tall and my legs.

'You look so tasty' Jan exclaimed. 'Why hadn't we thought of something like this before?'

I caught a glimpse in the mirror of my lower body. It was glinting with the moisturiser that was drying into my skin but I couldn't deny it looked great. Once again back in the bedroom I was ordered to slip on the panties and stockings before Jan would help me with the rest of the dress. She rolled up the stockings and handed them to me so I could pull them gently up my smooth legs. My bulge was causing quite a scene in the panties and was extremely obvious. It seemed that Jan had noticed this also so her hands which had lost heat while shaving me were placed on my legs and the shock did the trick of causing my boner to subside. Jan grabbed the waistband and helped me tuck it all in as modestly as we could.

'Wow,' she gasped. 'You look amazing. All we need now is the dress, hat and, yes, something with that hair of yours. Plus a little touch of makeup or you'll just look like Tom' She moved behind me and grabbed my hair. A few minutes later and two plaited ponytails hung nicely. Grabbing the hat she plonked it on my head and fastened it in place. I eyed the dress and she smirked at me.

After a little re-adjusting and many 'wows' and 'oohs' from Jan while she fixed the dress and applied some makeup I was finally fully dressed. What I hadn't known was there was a pair of high heels that also completed the outfit. Jan slipped these onto my feet and stood back.

'OK. Bo peep. Give me a twirl!'

With slight difficulty at first I turned on the spot and was left with red cheeks when Jan was gushing at how 'pretty' I looked. A smack on my ass later and the order to get a drink while I waited. I tottered out to the kitchen while Jan ran off with a small package to the bathroom. I took a few walks up and down the kitchen in my nervous waiting and found that I was quickly growing used to the heels I was wearing. In the mirror by the backdoor I examined that I didn't actually look like 'Tom' but a tall and more masculine Bo Peep if someone really examined me. I prayed that the party would be dark enough that it would be hard to tell.

About half an hour later and well into my second drink, Jan emerged. I spilled a little beer onto the floor in surprise. She stood before me dressed as if the costume was a custom fit. Police Officer Jan looked amazing. Her hips, ass as she walked, her breasts nearly popping out from under the vest. I was in awe. She didn't give me much time to admire her as she grabbed her 'Tactical Bag' close to her and ordered me out the door to the taxi that I hadn't noticed had pulled up given the nerves I was feeling.

We arrived at the party half an hour later as the taxi swung into a gravel driveway. The house was decorated beyond recognition. I had only ever been there once so that wasn't saying much but it looked great. A smoke machine by the front door was really setting the tone. The house was a big two story building with converted loft and sat about 15 minutes from the edge of the nearest town. The driveway snaked for about 100m before anyone reached the house and we both gasped at what they had done to the place. There were hangings, lights dotted around lighting trees and the house itself, even more smoke machines and so many pumpkins that I lost count. I stepped out and nearly fell as the stones under my feet gave an uneven footing. Jan came around and hooked my arm and steered me to the front door. We found a chime and heard a booming crack spread through the house. We waited and couldn't see much movement in the house so assumed we were early. I was peering into the window next to the door when we both heard noise behind us and jumped!

'BOO' shouted a mummy figure. I nearly fell into a seat by the door while Jan laughed nervously. A light above the door flickered on and in the dim light we could see that the mummy was in fact Mark!

Laughing along with us he said 'Hey guys! Look at you two! I thought Jan had grown a few feet before I realised who you were, Tom! Great to see you both. Your costumes look great! Pretty adventurous!' Mark winked at me. He ushered us around the house to the back garden where things were in full swing. Jan set about explaining the mix up and Mark seemed to enjoy my uncomfortable state saying I was a "good laugh" for agreeing to it. While Mark grabbed us two beers, Siobhan wobbled over. She was dressed in a very revealing devils outfit. She had clearly been drinking early as she hugged us both very tighly and pressed herself right up against me. 'You're almost looking as sexy as I am, Tom!' She twirled and we could see a devils tail which looked like it was attached to her for real. She noticed me staring and wiggled her ass. 'Ooh, you like my tail do you.' Grabbing it she whipped it playfully against my legs and towards Jan also. 'Oooooooh. So do I ... It's a very special tail' she said and leaned close to Jan and me as she said this. I wasn't sure what she meant but clearly Jan did. 'Come on you guys. I'll introduce you to some more people' and linking us both she gave us a mini-tour while introducing us to some of the other people there. Some were from Jan's work who I thankfully had never met but most other people were complete strangers. Nobody seemed to take much notice of how I was dressed. I was getting more comfortable the more beers I drank and it helped that one of the gay couples were giving me complements from the moment we were introduced.

Jan stayed close to me as the night wore on except to spend some time chatting with Siobhan who was now so drunk that Mark was feeding her grapes and trying to get her to drink water. It was around two in the morning when the crowd started to thin out with maybe people remaining. We were sitting or standing on the back porch with a few people inside the house. Suddenly Jan suggested that we explore the garden a little bit. I took off my heels so I could walk on the grass and we headed towards the barn like structure at the back of the garden. This had also been done up and was like a little maze inside. Garden tools and an old motorbike had been pushed aside to make room for some hay bales and a skeleton hung at the back of the barn. I made to turn back towards the door when Jan grabbed my wrist and something cold enclosed around it.

'Come here Bo Peep' she said and forced my hand behind my back. 'You think I wouldn't notice you checking out the Devil? We can't have you tempted by that. I'm afraid you need some punishment.' My other wrist was bound also and I found that Jan had secured a pair of handcuffs on me. I laughed and Jan smiled at me. We had never been this adventurous before and I found myself getting aroused by her actions. Jan sat me down on a hay bale and stood over me. I glanced over my shoulder to make sure we were alone and said. 'Sorry... um... officer.' I almost giggled.

'I couldn't help but stare when I saw you staring at her too.'

Jan leaned in close to my ear and said,

'You're right... I was checking out her ass and her special tail. Do you want to know where it really goes?'

As she said this it dawned on me and shock went over my face realising that the tail looked attached as it was going inside Siobhan.

'Good girl,' Jan said. 'I knew you'd figure it out sooner or later.'

She grabbed my hair and pulled back my head. Her mouth was pressed against mine and her tongue darted into my mouth. The fear of being caught like this was vanishing the more time we spent here. I could smell the perfume Jan was wearing and it caused me to tent even more in my panties. Jan stood back and took out her nightstick. She paced up and down and her ass was a sight to behold.

'What do you think we should do with you then? Do you think I should teach you a lesson for staring at other girls without permission? What do you say Little Bo Peep?'

I swallowed and said, 'Yes. Show me the full force of the law.'

Jan stepped closer again and forced my legs apart with her knees. She brought the nightstick between my legs and ran it up my thigh towards my stiff cock. She smirked and dropped the nightstick next to me on the hay bale.

'Stand up and bend over the bale' she firmly ordered.

I stood up and seeing that I was struggling, Jan unlocked one of the cuffs and re-fastened them with my hands in front of me. I was free to kneel on the bale and bend over. Within seconds there was a sharp slap on my upper thigh just below the bottom of the short dress. I yelped as I looked back and Jan had a devilish smile on her face. She took them hem of the dress and raised it so that my ass was exposed, only encased by the flimsy panties which were being stretched by my rock hard cock.

'Count each spank that you get and maybe you'll get a reward', she demanded.

SMACK

Jan's hand came down on my right cheek and caused me to slightly lurch forward. I caught myself and began counting. With each smack Jan alternated which cheek she was spanking. After ten hard spanks Jan stuck her fingers into my waistband and pulled the panties down to my knees. As I was facing away from the door I could only hope that there was no audience enjoying the view.

Groaning, Jan rubbed my cheeks and pressed herself up against my ass. She leaned over my back and I could feel her breasts pressing into my back through her costume. I could also feel the nightstick that Jan had obviously put back into her belt holder.

'I told you we were going to have some fun tonight. But I haven't been 100% honest with you Tiger,' she groaned this into my ear as she grinded against my ass. 'There was no mix up at the shop. I wanted this to happen. I wanted to dress you up and for us to end up in this position. Remember years ago when we got so drunk and I played with your ass for the first time and you admitted that you'd love for me to have complete control some time. Well tonight is just that.'