Crossdressing Vacation

hfernandez1983

Pervy Kinky Author
Joined
Sep 1, 2014
Posts
397
Hi,

I have currently finished writing 4 chapters of a crossdressing, pegging and gender play series titled 'Jenny' & 'Mike'. Although I had posted in the forum earlier that I wanted to write an individual story for Halloween for these characters, I am kind of now going in another direction. This will be a new series of stories for the characters and will further explore the themes I mentioned.

Here is my story idea outline. It's long and features what will happen in the story series. I would love to hear input from others and would welcome any ideas or suggestions as well.

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1. The weekend in the ‘Jenny’ & ‘Mike’ series was good and Michelle and James thoroughly enjoyed themselves. But James has been busy as of late. Even though he works from home, he has had to travel for the last couple of weeks and Michelle herself has been rather busy. This has left no time for “fun” times for them, be it vanilla sex or pegging.

2. Michelle decides that they need a vacation to have some fun and just unwind. So they start looking for something where James would not be prejudiced as ‘Jenny’, because Michelle wants James to be en-femme the entire time.

3. They come across a Hotel or Mansion holding a Private Party week during Halloween or maybe New Years?. It has all kinds of fun activities which are mainly centered on Crossdressing for both genders and Pegging. Once a booking has been made each couple is sent a list of rules.
a. A week at like a lifestyle resort sounds good. But then how do you think I should play it. Because at the resort I would want a lot of couples and single women there. No men allowed. The only men allowed there are crossdressed men. Plus all the genetic women (from a couple or single) have to be dressed in masculine attire.
b. But what if I use a private mansion instead of the hotel ? The only hiccup here is how would they ever know about this private party? How do they even get invited to this exclusive event? Same as above. A lot of single women and same dress code applies.

4. The hotel / mansion (whichever is chosen) has strict rules.
a. All couples / singles are to arrive at the venue dressed as the opposite gender.
b. All genetic women are to be dressed in male or at least masculine attire at all times.
c. All genetic women are to be wearing a strapon cock under their clothes at all times.
d. All genetic men are to be dressed up in female attire at all times (which include wig and makeup and breast forms).
e. All men dressed as women are to always be in stockings and garters except for certain events or when using certain facilities. NO EXCEPTIONS.
f. Day time is for casual mingling with other guests. No rude behavior will be tolerated.
g. Day time wear for women dressed as a man is casual or semi-casual or as per dress code.
h. Day time wear for men dressed as a woman is conservative or as per dress code. Nothing risqué at all. Also see point 4c.
i. During evening events strict dress codes will be provided to guests and they have to make sure that they are carrying all the appropriate wear to the venue.
j. All couples are provided with the itinerary of events and if a successful booking is made then each couple or individual must take part in all activities.
k. Any kind of misbehavior or prejudiced behavior will not be tolerated and that will cause grounds for removal of guests from premises without a refund.

5. Itinerary for activities is as follows:
a. Day 1 – Welcome Day. (SUNDAY)
i. Morning / Afternoon.
1. Arrival and check in. Time spent as per leisure.
ii. Evening.
1. Welcome dinner and entertainment at private banquet hall.
2. Mingling with other guests.
3. Leisure time for couple as per their wish.

b. Day 2 – Sex Club Night. (MONDAY)
i. Morning breakfast.
ii. Afternoon.
1. Lunch
2. Mingling with guests.
iii. Dinner & Drinks 6:30pm to 7:30pm or 8pm held at the private banquet hall.
iv. Sex Club Night event.
1. Held at Sex Club inside the vicinity of resort or mansion.
2. Timings 8:30pm onwards.
3. All genetic women are to be dressed in male suits. Same outfit as dinner will do.
4. All genetic men are to be dressed in conservative evening wear. Sexy underwear must be on under clothes with stockings and garters.
5. Each couple will be provided with a small room with open doors. Crossdressed men must be stripped down to their lingerie during sex, while the women (from the couple) will remain fully clothed in their suits and can release their strapon through the zipper in their pants.
6. The single women (dressed in suits) can move around freely in each room and watch couples fuck. The single women are allowed to finger themselves as they watch. The single women are also allowed to touch, caress and grope the crossdressed men as they get fucked.
7. Single women will not be allowed to join in with couples. They are there as mere spectators.

c. Day 3 - Threesome Night. (TUESDAY)
i. Morning breakfast.
ii. Speed Dating.
1. Rules are just like speed dating. Each couple will sit down with a single woman for a set minute of time.
2. Couples can discuss anything with the single women.
3. General idea is to mingle as well as find a third partner for Threesome Night.
4. Couples can choose anyone right in the middle of the speed date and leave the venue with the selected woman.
5. If by the end of the speed date event, a couple has not selected a partner then they will be provided one by default. Said partner cannot be changed.
6. Once a partner has been chosen, the couple can have lunch with them and spend the remainder of the day with them.
7. Dress code is semi-casual for genetic women.
8. Dress code is conservative for genetic men.
iii. Evening.
1. Each couple will be given a private table for 3 at dinner.
2. Couples to retire with their respective third partners.

d. Day 4 – Gangbang Night. (WEDNESDAY)
i. Morning breakfast.
ii. Afternoon lunch and leisure time.
1. The woman from each couple must inform the previous days speed dating event host of atleast 5 names that will be joining the couple in their bedroom for gangbang night. Time limit is by lunch time.
iii. Evening.
1. Dinner.
2. Dress code is formal i.e. suits for women and cocktail dresses for men.
3. Each couple will be provided a separate private table for dinner at the banquet hall, while all single ladies will be seated at a separate group table.
4. After dinner couple must return to their bedroom or maybe a room in the sex club?. At 9pm the group of women selected for gangbang night for each couple will arrive in their bedroom or the sex club room. The woman from the couple may join in the gangbang or simply be a spectator.

e. Day 5 – Public Sex Day. (THURSDAY)
i. Morning Breakfast.
ii. Afternoon Lunch.
iii. Evening Dinner.
iv. Couples can have sex anywhere in the resort. No area is off limits. E.g. Couples can fuck in the restaurant during breakfast, lunch or dinner, resort lobby, resort grounds etc. (Any ideas for where else they can have sex).
v. Anyone (including other couples and singles) can stand and watch as a couple has sex. Groping, touching of the crossdressed man being fucked is allowed as per consent of the woman (from the couple) doing the fucking.
vi. Women can join in during the sex act as per consent of the woman doing the fucking. This is not limited to only single women, but women from couples may join in too.

f. Day 6 – Underwear and Lingerie Party Night. (FRIDAY)
i. Morning breakfast.
ii. Afternoon lunch & leisure time.
iii. Underwear and Lingerie Party Night.
1. All genetic women must dress in male underwear i.e. boxer shorts or briefs and must wear a tank top or wife beater (or whatever it is called). Women may choose to have their strapon cocks in full view via their boxers or briefs.
2. All genetic men must dress in sexy lingerie i.e. Bodystockings, teddies, camisoles, corsets etc. Garters and stockings not required if a bodystocking is worn. If only bra, panties, stockings and garters are worn then a robe must be worn.
3. A couple may fuck at the venue of the party. Consent can be given to any woman whether single or from another couple to fuck a crossdressed male at the venue.
4. A couple may also invite another couple and/or single/s women to join them in their room.

g. Day 7 – Black Tie Night (SATURDAY)
i. Still not sure what to do with this….maybe this is the final night or maybe not…?


This is where I end. Day 8 which is Sunday everyone departs the resort.

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How does this sound? Do you think anything needs to be changed or improved. I would love to hear from others about what they think.

Regards,
H.

P.S. I am going to be writing this story series.
 
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