Halloween in heels ++++1st time

[highinheels]

Well, I signed up so I could share my story.I have been reading this forum for a while but never posted untill I saw so many people like my self. If you never hear of others feeling like the same feeling you figure your the odd one out. From the age of 5 I spent lots of time with a girl that lived across the street that was my same age. I was an only child and my Mom was a single parant so during the summer Vacation I spent everyday been looked after by the lady across the street.( She was the Girls mon) I didn't have many friends as no kids lived down the street apart from my and the Girl. Anyway,We played the usual kid games and one day she decided to dress me up as a girl.I didn't mind as she was my friend and thought nothing of it been strange, it ended up almost everyday we would both be dressed as girls and played together.She ended up dressing me in everything she had plus here sisters clothes which was about 3 years older than us .Her mom never really seam to mind and would sometimes do out her in bows etc. After a couple of weeks of playing together here sister came home and saw me dressed as a girl. I'm not sure where she used to go during the day but this was the first time I had saw her.I remeber her thinking it was fun and wanted to get into dressing me in everything she had too. I was like there Barbie doll, it wasn't long till the sister brought some of here firnds over and my dressing was done everyday day by 4-5 girls. This is going back 30 years, there was nothing sexual about it in any way. At that age we didn't even know what sex was.I wasn't really feeling wierd about it but I looked forward to the next day as they all used to take turns dressing me up and playing with my hair and practicing makeup on me.One day before I was due to go home ( at the end of the day) the girls Mom said " you don't tell your mummy you dress up over here do you?" I said No. She said "You might not want to tell her has she might not let you play over here any more". I never said a word to anyone! We played these game for 2-3 years untill her family moved out of town and I never saw here again. I never told anyone about this, and I had this empty feeling inside........ This never became and issue untill i went into high School and was around more girls, I was always attracted to girls and ocasionally wanted to dress like them too...... These feeling would come and go, there never stayed for more than about 1-2 weeks. I dated a girl at the age of 17, She was 18 and was about 2" shorter than myself. I once stayed over her house when her folks went away for the weekend. We watch TV and drank some kind of Shots ( Never really a drinker , So I don't know my drinks) untill we both got kinda drunk. We went to her bedroom and she decided to show me her underwear she had bought that day, she also showed my her nightie she bought. I said" I always wanted to sleep in a nightie but my Mom would never buy me one" She burst out laughing and said " You should wear one tonight" I was so excited but tried to play it off....I said NO, What if you tell my friends. She only offered one more time and started to undress me and put it on me.She also removed my boxer shorts and give me some of her underwear and told me to weat those as they match. The nightie was black silky type and came to just above my knee with spegetti straps. I was thought it was so cool , so did she. She then said " Have you ever wore highheels" I said NO. She went to her sisters room and came back with some Black High heels with one ankle strap and a hugh spike heel. She said her sister had the biggest feet in the family and they should fit me. She helped me put them on, there fit a little tight but I thought they were great. I didn't know what to expect but I loved them. She said you walk around the house in them , the more you walk in them the better you will get. She asked if I would like to sllep in them . I said Yes. We layed in bed together, Sex was no on my mind and I don't thinl she was thinking about it either as she fell asleep quick. The next morning I thought it was a dream, untill I felt down to my feet and felt the tight pointy heels that were still on my feet. Thinking back she might have played barbie doll with me if I had mentioned it. We woke up and we ate breakfast together. She asked if i wanted to take off the clothes and I said i kinda liked them. Let me fast forward a few years..... Last year my wife I booked a cruise to Mexico, the last night was Haloween. My wife for weeks prior had been looking at cool costumes for her , they all looked so appealing to me as I had always been into cross dressing but hardly ever had the chance. She finally found her costume which was a sexy Boo peep with white high heels. We then started looking for costumes for me, all kinds of crappy Builder , Policeman, wolf etc .Stuff I had no intrest in after looking at after all of female costumes. After looking at lots of guy stuff and I said " No, I don't really like any of these",In the end she said. "What do you want to be then?" I waited....and then said ,"I wanted to dress in something Girlie " Then a big Pause.......... Part 2 soon

[heelsinmass]

i cant wait for thr rest of the story im going on a cruise soon, not on halloween but close its the first week in OCT

[c_heels]

Can't wait for the next part!!

[highinheels]

She said ....You want to dress like a Girl ? I said...Yes, Or something Girl related. After a Pause..She said Your not Gay are you? I said, Not at all, Never crossed my mind. Pause.........I explained my story . I little more detail than above an she listerned.To the whole thing. I said I wasn't interested in living any kind of lifestyle and going out dressed up to clubs etc, Just dress up at home . She then, Asked...Have you tried on my clothes while I was out.... I said yes, almost everything . She then smiled, and said let see how you look then. I was very nervous as it all came together pretty quick and I didn't have time to prepare myself for this. She asked me what I like to wear, I said Skirts, dresses, Bras, pany hose and I even tried on her Corset from Fredricks of Hollywood which I broke. I ordered a new one to replace it without saying anything,It was there "Ultimate Corset" which wasn't that strong plus it was a little small for me. We tried on a few things together and had so much fun, the only thing missing was shoes and some of her things were too tight to close. We then got on the internet together looking for shoes, It was funny looking together as we had very similar taste and liked the same kind. We spent hours looking at sites and ended up stumbling across this forum. Well after picking out some black 5" heels strappy shoes and a couple of pair for her we ended up looking at Corsets. I had always liked watching those old movies with the Women would be getting laced into a Croset by her maid.....Anyway. We found a company that made custom Corsets from England, There were kind of expensive but after looking at there site they claimed that there products are not fashion tops but real deal Corsets. We ordered one for my size minus 5" I think in white. 2 weeks later it was here, we opened it together and I was kinda of scared that it was much more heavy duty than the Fredricks one with metal boning all through it but on the other hand it looked so delicate and inocent on the outside. At this point she helped my on with it, the instructions explained to how to lace it and explained it should have a 2 to 3" even gap when laced correctly.It also explained to lift your arms while lacing it which we did, I held onto the door frame while my wife slowly tightened the laces. I was amazed how quick it tightened, and how tight it felt. It felt great, very tight to the point I couldn't take deep breaths at all, She had a 3" gap all the way down and then tied the laces off.I forget to mention I had been wearing the new shoes off and on for a week at this point getting used to them. I walked around with the Corset and shoes for a few minutes then it was off the the closet again.I tried on this black mini dress that didn't come close to zipping up the last time and this time it zipped. It was tight and she was worried it might break the zipper so we tried some other things on. I ended up in a very tight black pencil skirt and white blouse which I just loved. I stayed dress that way all night and she was totally cool with it, in fact she made walk all over the house to get things for her. The corset was way tightly than I dare let on in case she made me take it off and the skirt would no way it would fit without it.The shoes were kinda of tight and hurting my feet after almost 5 hours of wearing them , I tried to reach down and adjust them but I couldn't bend to touch them with the corset on. I was a great feeling even though I was starting to hurt. I was time for bed now, I said should I take this off now...She said no. keep it on for a while as she changed into her nightie and then climbed on top of me. It was so erotic.....After the longest and best love making we both laided there untill we fell asleep. The next morning I woke ealry and realised I was still dress this way, I was kinda of excited that I had spent all night like this and i couldn't take it off as the coset was tied at the back with the knots up high then threaded into a pocket so the strings didn't show and I couldn't reach the straps on the shoes. I was enjoying it and I was totally under her control, she knew that and she enjoyed it too. Once we got up she said we should eat some breakfast then I could help her with some house work. I said and keep the clothes on ? She said i could put some work clothes on so not to mess up her nice stuff. I was OK with that as I help clean anyway. After some begals for breakfast and a glass of orange juise the corset began to feel tighter than ever. I told her..this corset sure is tight after eating, she said it will not be after some work.......I didn't say anything back but I didn't want to sound like I was the one wanting to remove it. After I did the dishes I went into the bedroom where my wife was getting dressed. She had layed a dress on the bed, she siad lets see how this looks. It was a long cotton dress with a wide skirt in a horrible brown color. I said I don't want to try it on, it looks like something my Mom would wear. She got kinda mad and said it was her sisters which she loved but her sister had got too big for it and it was going to good will. I tried it on and it fit perfect , it was almost fitted to me it fit so well. She said , lets start ceaning. I said , no way. I'm ready to change into my clothes. She said....I don't think so, You can clean the house and we'll see about it later.I hated the dress but then again, I was still wearing a corset and 5" heels under it which I hadn't been able to do a month ago with her. I agreed.She said it would be worth it later on for me. I cleaned, vacumed, washed , scrubbed all day while she watched me and spent the day watching TV and talking on the phone . My feet were on fire but she still found more things to do and clean. We both enjoyed it, after about 6 hours of cleaning she said I could sit down and watch some TV with her and take a break.We watched TV for about 3 hours , She then said come on, as she led me to the bedroom. She laid me down on the bed and again climbed on top of me. After the longest love making to date we both laid there for a while. She said this was more fun for her than she thought it would be. I said I liked it too . She then said , What if I was to tie you up and keep me this way till morning. I didn't.... didn't know what to say no , but I was kinda of affraid affter the last 10 hours or so. I said sure, as long as i could end it if I was ready. She smiled and then went to her closet. She came back with some panty hose and some scarfs. She then tied my 2 wrists together and ankles together and I laid diagonal across the bed while she then tied me to the bed posts.She then taped me mouth with my own duct tape and blind folded me. After and another love making session we both layed there and she read her magazine for what seamed like hours and I ended up falling asleep. The next morning was monday, she untied me and helped me get undressed, I could hardly stand and I felt drained. My feet felt strange with been in heels and I went to take a long shower. She left for work and said good bye. I went to work and felt very strange, I felt like I wanted to tell someone about it .it was so crazy and fun at the same time. I didn't tell anyone and we texted each other off an on during the day.That was one crazy weekend, I enjoyed it but almost though I might have bitten off more then I could chew. Was she going to want to do this all the time, I spent the whole weekend dressed and helpless. It was 2 weeks untill the cruise. I guess she was totally OK with me been dress up at this point. The crazy thing is , this is all true. Part 3 soon

[zebra heels]

you are one lucky guy cant wait to hear the rest of the story:smile:

[highinheels]

Part 3 Well for the next 2 weeks untill the cruise we didn't do anymore carzy stuff, infact She never mentioned it and I didn't want to bring it up as I was a bit shy to start talks again. We're now packing for the cruise and still nothing has been said so bring it up...I say , Should I pack my haloween outfit in your case or mine in case they get searched? She said ..oh yea, We never figured out what your going to wear.Pause... She then says, " I don't want you dressing like a Girl all the way in public" I said, OK...What are your thinking? She then said, What do I like to wear the most? I said , Shoes, Skirt and I kinda like the Corset. She think and says, Why don't you wear female stuff on the bottom and male clothes up top, That way it's kind of a Cross dressing outfit that is not too serious. I agree , I think I will feel more at ease that way. So we pack the black Pencil Skirt, my black 5" heels, new Panty hose by leggs and the corset in her case. We get on the cruise and everything is great, We leave out of Miami on the Saturday, Halloween night is the following Friday. We go to dinner the first night and meet the people at the table, we're at a table for 6 and it's all couples. One couple spoke almost no English at all, the other couple in there mid fourties from Denmark and spoke very good English...Needless to say we spoke to them all night and got along really well with them. There about 15 years older than my wife and I but we got along well. As the week went by we spent a couple of days on and off with them, met them at dinner for the evening meal , went to a couple of shows etc. Well, then the question came (From them)" What are you guys going to be for Haloween" My heart sank, I feel very wierd as I know these people now and they feel like friends. My wifes takes over, She said . She was going as Sexy bow Peep and I was going to be a cross dresser. They thought that would be great and both looked at each other and kinda grinded. They then said that he was going do the same kind of thing. That made things much easier, I wasn't into the whole dresing up and hanging out with guys or nothing but it was halloween. Turns out he was going to wear some kind of flower patern dress of hers ( He was about 270 lbs) My wife tells her I'm going to wear a corset, her eyes light up. She said her mother used to be a Corset maker ( not sure of the term) for a few years. I'm half listerning in as he is talking about something else. Well there both talking about getting dressed up before dinner as that's what everynoe else was plannig. So Saturday comes ( Haloween) and we spend a lazy day sleeping in late ( As we will be up late) and then go sit by the pool for a while. We go back to room and start getting ready, We both get showered and start getting dressed. I borrow her underwear and put on the new panty hose, she helps me on with the corset and starts to lace it up. It starts to get tight and then she gives me a ...Oh...mmmm...Aw. She says, "It looks like you have put on some weight since you wore this, it's a lot from closing " I didn't think about that, I have been eating everything in sight on the cruise all week. She ties it off and tells me to wait for a few minutes while she gets ready and then she will tighten it up some more. I watch TV for a bit, she runs to use the Iron on the ship and says she will be right back. She comes back after a few minutes with the lady from our table, Oh Crap, I'm wearing Panty hose and a Croset..... She is talking to my wife and says something about candle wax...I start to freak out, I don't want anything to do with this lady and candle wax. My wife produces a candle from her bag, it was never lit in the room but she always has candles everywhere. The lady says stand up, we need to wax the laces so they don't get too tight to pull. After my wife asks me , I stand up... and turn with my back to them.The lady gets the candle starts rubbing on the back of the corset and laces...I'm thinking to myself " What is this all about .. She then starts pulling on the laces and the corset starts to tighten even more, She says." there..See ..Easy...See. " . She says "you help", Pull that side a little and I pull this side... The corset starts to get real tight, even tghter than last time...By far. My wife says, yes much easier. It hurts her hands last time. the lady,,,Says...yes..You should use towel around the laces. My wifes goes to get some small hand towels, I'm standing there and the corset is so tight I am almost panting. I'm trying not to let on too much but I'm hoping there done. They wrap the towels around there hands and pull some more, it seams to move a lot each time they pull, I guess that wax makes a big differance. I'm still taking short breaths and say hold on guys, but it's almost hard to say anything. They both keep pulling in short tugs, the corset keep getting tighter and tighter.She says OK, I tie off the top now. I'm like....Holy C**p...This is too much. She ties off the top in a couple of knots, then doubles the knots over and tucks them into the pocket while my wife holds to bottom ones tight.The lady then takes the bottom set and starts to pull again ,,The Corset keeps getting tighter, She says, OK, That is good..and ties off the laces and seams like a double knot. She tells my wife, you only pull this end to relase or it will tangle and you will have to cut the laces. With that she leaves, and says...See you ... My wife says, Wow it's almost closed, it had about 1 inch of a gap. Your waist looks so small. I can hardly breath, I thought this is really too much, there is no way I can do anything. She helps me on with the skirt and zips it, She says wow, it is loose on you now, Thats good, you wont break the zippy now. She then helps me on with the shoes and I can hardly stand. She give me my White shirt and black jacket and says, Ok your done. I can hardly breath or say too much, it feels so hot in the room and my eyes are watering. I try to sit but I can't bend, I end up laying on the bed while she does her makeup and gets ready. I say I really think I might pass out, I can't wear this tonight. She says ..well your not taking it off now, it took us all that time to get your dressed, you can get used to it for a couple of hours .I havn't really eaten much that day but I figure there's no way I can eat now ,There's no room to do anything. I lay there thinking this is a bad isea while she gets ready. Part 4 soon( Run out of time)

[Hiline]

I have no idea what to say WOW!!!! and maybe another WOW!!! . I hope we see this to the end . Thankyou for a great read so far