The perfect end to a fun packed holiday.

Tell us about your latest, greatest, best, worst or simply funniest bondage/selfbondage/chastity/CD experience. Only true stories please!
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bounddosster
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The perfect end to a fun packed holiday.

Post by bounddosster »

My wife and I have recently come back from a holiday nothing fancy just a holiday caravan by the sea to get away from it all. However it turned out to be a great kinky fun filled holiday. It all started with a game of Ludo which soon turned into strip Ludo and when my clothes were gone we played for forfeits and £1 coins.

From this game came a very surprises and firsts from my wife. Which has now resulted in me be the proud owner of several pairs of female knickers and two skirts.
There were various other forfeits but I'll concentrate on the crossdressing, if you can call it that, for now.

My wife although kinky had not shown any real interest in crossdressing me until this adventure last year,
viewtopic.php?f=15&t=14176

Then life, as it does, got way more complicated and nothing really became of it until last week. When one forfeit given to me was having to buy some female knickers (panties) and then wear them according to how many days dictated by looses in future games.

Me having to wearing female underwear was nothing new to us and during our years together it had entered my life at odd times in various ways but the next forfeit was something new when my wife declared I was to buy a skirt and again wear it as the forfeits dictate. To hear my wife say this was a surprise with a thrill of excitement shooting through me at the prospect but also combined with a nagging doubt of this will never happen.

The underwear was bought from a factory outlet store, we went for a cheap multi pack of four plain-ish black with a bit of a frill top and high cut fit, my wife seemed a little disappointed we couldn't find more reasonably priced more feminine style but these were chosen over more elaborate ones as we were unsure of my size with me not having worn any knickers for years. More fancy and feminine pairs were promised and two such pairs were placed on my pillow yesterday for me to find last night and now reside in my drawer waiting to be worn.

The skirt or skirts as it turned out to be were bought form a charity shop, they are if not new certainly almost new and very reasonably priced. We had a rough idea of my size from the jeans previously bought and we opted for the shortish purple in a size 16 and a lovely black faux leather in a size 14. Unfortunately the black skirt didn't fit, I need to loose some more weight to fit into it so there is an incentive to keep up the diet, which along with a few hiccups here and there is general going well. Two stone (28lbs) lost since February which considering our life events lately to me is amazing.

This is confession time, I've never really considered myself a crossdresser and have only ever messed about at the fringes but I have to admit that when I tried on these skirts they felt fantastic, not only in a sexually exciting way but also in a comfy, relaxing, and a this feels right sort of right way. I also had the feeling of embarrassment being dressed in a skirt in front of my wife but it all seemed very erotic and maybe dare I say natural, which is a little disconcerting.

From various forfeits earned during the week I found myself wearing knickers everyday, that is when out and about as due to other forfeits I spent all my time inside naked with my cock lock locked in place (see link below), which incidental will remain locked on for another seventeen days.
viewtopic.php?f=12&t=13515

As a result of these games I found myself with what I considered a hardcore major forfeit. I had to drive after the holiday wearing a skirt and knickers. As it turned out I was dressed nearly all feminine as my top was a t-shirt, unisex I guess, on my feet wear trainers with no socks, around my waist was the purple skirt with enough buttons undone just to show the very bottom of the crouch of my black knickers and plenty of thigh.

Apart from once trying it in a half hearted way and getting caught I'd never worn a skirt much and certainly not outside and I'd never driven even a short distance in a skirt before.

I earned this forfeit on the Tuesday and my wife taunted me all week by having the skirt on display draped over the side between the eating and lounge area through which I gad to pass many times a day throughout the week.
The new skirt taunting me many times a day,
The new skirt taunting me many times a day,
Saturday mourning came and it was time to leave and go home. As there was quite a few people about I was permitted to load the car wearing all the above clothing but with jeans instead of the skirt on, with the intention of me changing into the skirt in the car just before leaving but there was not enough room for me to change in the car and I had to do it outside the caravan behind the decking railings then walk across to the car. This involved walking about ten metres mostly fully exposed to the approaching road and any one walking past. A man did walk past while I was changing just as I had removed my jeans and I had to duck down out of sight while he pasted by. My wife had the camera out but only managed one poor shot of me walking across to car as I was moving at a fast pace to get inside the car. I did have thoughts of her locking me out of the car like she use to when I was naked but thankfully she didn't.

I handed my jeans to my wife and she promptly threw them into the back of the car and with it being an estate car that meant the jeans landing in the boot and totally unreachable without me having to get out of the car and walk around the back to open the tailgate.

The last thing to do before setting off home was to deliver the caravan key back to the reception which meant parking in the front carpark while my wife got out and took the key over to the reception office. I was nervous about the other people around but luckily it was quiet but my nerves where not helped when my wife left the car leaving the door wide open meaning I had to remove my seat belt and lifting myself from the seat and lean right over to close the door so showing that I was wearing a skirt and probably showing the bottom of my knickers out of the drivers window. I glanced up at my wife walking across the car park and saw her looking back over her shoulder with a large grim across her face.

When she returned to the car she opened the door as wide as possible then sat in the seat but kept the door open until after she had put her belt on and was sure she was comfy, Then when the door finally closed the “drive on” instruction was given and I started our one hundred and ten mile home.

Usually I get board driving this sort of journey but this was different, I was careful to drive well and stay within the law, I usually do but you know how habits creep in over time. I was driving like I was taking my driving test again, My wife even commented later about how good I'd driven her. I didn't want to attract the attention of any police or have an accident which would mean getting out and or interacting with other people while dressed as I was. I don't think other drivers passing by or people at the road side could see anything but that didn't relieve my self- conciseness any.

As we neared home I had a choice either to arrive home and pull up on the drive in view of the neighbours still wearing the skirt or to stop in a layby about half a mile from home and change back into my jeans. I opted for the later as I didn't want the neighbours finding out I had a new kink when I believe they are still just getting use to the idea of me being a naturist.

Opting to changing had it's own complications. I was going to have to get my jeans out from the tailgate and what if someone else was parked in the layby. Much to my wife's disappointment the layby was empty as I pulled up and stopped. I looked around then opened the door, I could feel the cool breeze between my thighs as I stepped out of the car and started walking cautiously to the back of the car. I popped the tailgate and reached in for my jeans I had to learn forward slightly and as my skirt rose I felt that cool breeze again, brush the backs of my things getting higher and higher as more naked flesh was exposed as I bent over to reach my jeans. I grabbed the jeans and quickly looked around, stood up straight, pulled my skirt down and closed the tailgate then I returned to the drivers seat and closed the door.

Removing the skirt was easy as I just undid each button down the front and slid it from beneath me. Getting my jeans on was more of a struggle. As I sat there in my black knickers trying to undo the double knots in my trainers several cars went past but none ventured into the layby. A thought popped into my head, what if a neighbour saw the car they might think it strange I was parked there and thinking I needed help they might pull up and offer assistance to find me sitting there dressed in ladies black knickers and a t-shirt. A dozen excuses ran through my head as to why I'd be dressed in such a manor but none sounded the least bit plausible.

Soon the trainers were undone and off, I slipped on my jeans by having to lift my arse of the seat high enough to pull them up again putting me in full view of the window but I was soon dressed and we headed home. After 110miles and three hours we finally pulled up, unpacked and put the kettle on. Then I had to strip off naked as my wife reminded me I still had three more days of my indoor clothes ban to complete.

I found the drive to be very exciting and I had eight dry orgasms through out the journey and when home my knickers were very damp from pre-cum. I also found driving in the skirt to be very comfy and didn't have any of the usual tiredness when arriving home. So all in all it was a good end to a much needed fun holiday that might well have further implications for the future.
My wife had the camera out.
My wife had the camera out.
She wanted a flash of thigh.
She wanted a flash of thigh.
Sorry, the photos are a bit fussy due to being taken from a video.
I do believe these are my first ever cross-dressed photos on boundanna, well anywhere.
(Excuse the hair there has been little time for major grooming lately.)
That's my excuse and I'm sticking to it.
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

I just noticed in the lower photos it actually looks like I have small but pronounced breasts. :) it must be from the camera angle or perhaps I need a bra. Don't tell the wife it will give her ideas, second thoughts tell her please. :D
That's my excuse and I'm sticking to it.
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kinbaku
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Re: The perfect end to a fun packed holiday.

Post by kinbaku »

bounddosster wrote:I just noticed in the lower photos it actually looks like I have small but pronounced breasts. :) it must be from the camera angle or perhaps I need a bra. Don't tell the wife it will give her ideas, second thoughts tell her please. :D
I loved your story. What a good woman you have, with such good ideas for this thrilling ride. :mrgreen:
If you give me her e-mail address via PM, I can whisper a few extra ideas to her (such as a good bra for you :rofl: ).
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

kinbaku wrote:
bounddosster wrote:I just noticed in the lower photos it actually looks like I have small but pronounced breasts. :) it must be from the camera angle or perhaps I need a bra. Don't tell the wife it will give her ideas, second thoughts tell her please. :D
I loved your story. What a good woman you have, with such good ideas for this thrilling ride. :mrgreen:
If you give me her e-mail address via PM, I can whisper a few extra ideas to her (such as a good bra for you :rofl: ).
Yeah! she great. Thank you for the comments about my adventure, not so sure I got across the thrill, excitement, fear and embarrassment of it all, I'm not a great a writer.
As for talking to my wife, She can always use more good ideas, not sure I could. :D
That's my excuse and I'm sticking to it.
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Shannon SteelSlave
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Re: The perfect end to a fun packed holiday.

Post by Shannon SteelSlave »

bounddosster wrote:I'm not a great a writer.
That's the point. You've never been a liar.
Bondage is like a foreign film without subtitles. Only through sharing and practice can we hope to understand.
A Jedi uses bondage for knowledge and defense, never for attack.
I am so smart! I am so smart! S-M-R-T!....I, I mean S-M-A-R-T!
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

Shannon SteelSlave wrote:
bounddosster wrote:I'm not a great a writer.
That's the point. You've never been a liar.
If I write fiction I say so but always been honest with my personal experience. I have had the luck of having openminded and somewhat kinky bunch of friends when I was younger. Most people I know now are open minded but the passion and madness plus less consumption of alcohol, from our youth has somewhat tamed us. Plus every girlfriend I had, bar one which didn't last long, has had a kinky leaning. It is amazing that once you know someone who is kinky, they will know another and them another and soon you realise there are more kinksters out there than you thought you just need to be open and honest with the right people and open yourself up to having some fun whether with others or solo just do it, life is far to short to f**k about with hang ups.
That's my excuse and I'm sticking to it.
TicleMeEndless
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Re: The perfect end to a fun packed holiday.

Post by TicleMeEndless »

Send to your wife another wish for loosed bet: no excuses like "i do this for a bet", "i just loose a bet", etc. :twisted:
Not all dreams must come true. Choice with a cold mind. Be careful. Not crazy as me.
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

TicleMeEndless wrote:Send to your wife another wish for loosed bet: no excuses like "i do this for a bet", "i just loose a bet", etc. :twisted:
Perhaps I'm being a bit stupid today but I don't really understand that?
That's my excuse and I'm sticking to it.
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bound_jenny
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Re: The perfect end to a fun packed holiday.

Post by bound_jenny »

bounddosster wrote:
TicleMeEndless wrote:Send to your wife another wish for loosed bet: no excuses like "i do this for a bet", "i just loose a bet", etc. :twisted:
Perhaps I'm being a bit stupid today but I don't really understand that?
I'm just trying to imagine the havoc caused by a bet on the loose... :shock:

You'll be cleaning it up for weeks. :mrgreen:

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
Come to the Dark Side - we have cookies!
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Shannon SteelSlave
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Re: The perfect end to a fun packed holiday.

Post by Shannon SteelSlave »

eeewwww?
Bondage is like a foreign film without subtitles. Only through sharing and practice can we hope to understand.
A Jedi uses bondage for knowledge and defense, never for attack.
I am so smart! I am so smart! S-M-R-T!....I, I mean S-M-A-R-T!
👠👠
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bound_jenny
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Re: The perfect end to a fun packed holiday.

Post by bound_jenny »

Shannon SteelSlave wrote:eeewwww?
The worst is when the bet goes feral. :shock:

Jenny.
Helplessness is a doorway to the innermost reaches of the soul.
If my corset isn't tight, it just isn't right!
Kink is the spice of life!
Come to the Dark Side - we have cookies!
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BoundInKasugai
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Re: The perfect end to a fun packed holiday.

Post by BoundInKasugai »

Sounds like a great experience, thanks for sharing! Sounds like you have a great partner, too! Being on holiday relaxed and miles away is a good way to explore kinks :lol:
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

BoundInKasugai wrote:Sounds like a great experience, thanks for sharing! Sounds like you have a great partner, too! Being on holiday relaxed and miles away is a good way to explore kinks :lol:
Yeah she is great far beyond the sex stuff, don't know what I di with her.

Not being what I consider a crossdresser as such, Yet... I'm a little confessed as to where she is taking this. I received two interesting yule tide presents from her. One a short denim skirt and another pack of panties. beats the washing machine I got the other year, When I unwrapped the panties she stated I now had a pair for everyday of the week. I realise to some this would be a dream come true but I'm totally unsure how to read it. But hell I'll go with along with it and see what happens.
That's my excuse and I'm sticking to it.
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kinbaku
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Re: The perfect end to a fun packed holiday.

Post by kinbaku »

bounddosster wrote:... But hell I'll go with along with it and see what happens.
Have nice travels with her into the unknown that awaits you (I already had some ideas what she could do with you to please her :twisted: , ...
... but i think she reads my mind :mrgreen: ).
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bounddosster
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Re: The perfect end to a fun packed holiday.

Post by bounddosster »

kinbaku wrote:
bounddosster wrote:... But hell I'll go with along with it and see what happens.
Have nice travels with her into the unknown that awaits you (I already had some ideas what she could do with you to please her :twisted: , ...
... but i think she reads my mind :mrgreen: ).
Unfortunately I can't read your mind but feel free to share any ideas in a pm. :wink:
That's my excuse and I'm sticking to it.
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