Sissy boys dating guys

Isobel grinned when she finished styling my wig, “Daddy is going to be soooo happy to see you today!”  I still shared an apartment with my ex-girlfriend.  She had managed to lock me in chastity and use some photos she had of me wearing women’s panties to blackmail me.  Now it had gone further than I had ever imagined.  She felt it was time to send me out on a date with a hunky dominant bisexual she knew.  “He’s such a hunk,” she swooned, “but unfortunately I’m not his type – a submissive lil femboy is what really turns him on.  This is so fucking hot, watching my ex-boyfriend go on a first date with well hung adonis!”

I quivered with fear.  I had to admit I looked very hot.  My tiny penis hardened inside the steel chastity cage.  Oh my!  If I turned myself on what would my date think of me?  Isobel had picked my outfit well.  She knew that Daddy (she wouldn’t give me his real name but said that I would refer to him as Daddy until he decided otherwise) favoured the very girly feminine look.  Isobel was delighted to present me with a black off the shoulder dress.  “It’s basically a prom or young miss cocktail dress, with a taffeta petticoat, and the polka dots are especially girlish!  You have such a girlishly slim figure and great legs that you can carry off such an outfit with no problems at all.”  She handed me a pair of black lace panties, “These are delightful aren’t they!  You’ll notice that they are open backed with a heart shaped opening to display your pretty ass.  As you walk you’ll feel the taffeta and any breeze caressing your cheeks.  Any slight wind will blow the skirt up so be careful not to show your lovely bottom off to too many people!”  I gasped in horror but this only increased Isobel’s pleasure.  “Here is some sheer stockings and a garter belt, you’ll feel the gentle tug of the straps with every step.”  Finally she handed me my shoes, “These are 5 inch fuck me heels!  Strappy patent black sandels and a little silver anklet for you.  Even though they’re 5 inch heels Daddy is 6 foot four inches so he will still tower above you!  Also he thinks your name should be “Chastity”.  Isn’t that cute!  So Daddy will address you as Chastity.  It’s hard to believe you used to be quite arrogant macho male.  I am sooooo going to enjoy today!”

After Isobel did my makeup, attached my wig, filled my handbag, and checked my jewellery she decided it was time to go.  “Let’s go sweetie you don’t want to keep your date waiting too long.  I’ve booked a table for one near your table so I can keep an eye on you.  But this is your day.  The meal is in Le Grand Coq about a mile from here.  You know where it is so you’ll be walking there.”  I gasped, “Please can you drive me?”  “Sorry Chastity,” she smiled, “this is your hot date hun, I’ll walk a little behind you and see the reactions of passing people as you sashay by in your hot little outfit.  I hope you realise what a cocktease you are in that dress and heels!  Let’s go princess!”  “But…,” I stammered, “I’ve no breastforms on yet.  I have to put them on first.”  She gave a delicious smile, “It’s moments like this I relish, having my ex-boyfriend beg me to give him cleavage to show off to his hot date!  The fact your so desperate for breasts gives me even more pleasure in telling you you’re going to be flat chested.  I’m actually doing you a favour, Daddy said you can wear breastforms or a wig but not both.” I gasped with horror at the thought of going out in public wigless.  “So what do you say to me sissy?”  “Thank you Goddess Isobel,” I whispered as I was close to tears.  “I love seeing you so vulnerable, it really adds to your feminine fragility.  Let’s go now darling, you’ve a dreamboat of a date waiting for you!”

I stepped outside my high heels clicking on the pavement.  I felt totally exposed.  “Now sweetie,” Isobel smiled, ” you’re going to walk in front of me so it looks like you’re walking alone.  It’s important that you learn to go out on your own all dolled up.    You’ll attract a lot of attention dolled up so fabulously for a lunch date.  You look amazing.  Your legs look so good in those heels and that tiny dress, I’m jealous!  Off you sashay sweetie!”  I couldn’t do anything but walk off in front of her.  I was completely used to walking in very high heels and walked just like a girl with a gentle sway of my hips.  I hoped I was completely passable despite my flat chest.  Then, to my horror, I heard my phone ring in my handbag.  My long French nails opened my bag and took out my phone.  Isobel had even put a polka dot phone cover on my phone to match my dress!  The call was from Isobel, I had no choice but to answer.  “Hi hun,” I whispered.  “Speak up sweetie, I can’t hear you.”  “Hi Isobel,” I said a bit louder.  “Okay darling, do you see that group of women in front of you?”  My sissy heart sank.  “Answer my question sweetie, do you see that group of women out shopping in front of you?”  “Yes I do Isobel.  I’d better get to the restaurant quickly for my date hun.”  She ignored my attempt to change her plan.  “You look so hot hun it’s time to test it out on a group of pretty females.  You’re going to ask them where the restaurant is, just to make sure you know where it is.  I’m really going to enjoy my ex-boyfriend having a chat with some fellow females.”  I was even more conscious of my fuck me heels clicking on the pavement and the shortness of my dress, and the breeze on my bare bottom.  “Excuse me,” I stammered to the group of girls.  There were five of them, all very attractive with shopping bags from Forever 21, Penneys, and Miss Selfridge among others.  They all looked me up and down and my self-consciousness increased.  “Do you know where Le Grand Coq restaurant is?”  My voice, despite trying to make it more feminine, gave me away.  A couple of them stared at my flat chest.  “Why darling, do you have a date?” asked one.  “Yes, I do,” I was reluctant to say more than I had to.  “Your very sexily dressed for a lunch date, he must be very hot this guy.”  “I’d say he’s only one thing on his mind for this pretty little thing.”  They all laughed.  “You look really good in girl’s clothes, very nearly passable, guys will be attracted to you but I’m afraid quite a few girls will be amused by a guy playing dress-up so convincingly.”  “Your’re almost at the restaurant, keep going straight and it’s on your left, don’t keep him waiting!”

I arrived at Le Grand Coq with Isobel close behind you.  The very pretty maitre d’ looked up.  “I’m meeting someone for lunch, he has a booking.” “Certainly Miss, what’s his name?”  I blushed, “His name is Daddy.”  She gave a little smile and a slight arch of her perfectly tweezed brow.  “Ah yes, let me show you to your table.”  My heart was thumping as she led me into the restaurant to a seat right by the window completely exposed to the street outside.  My mouth almost dropped open as Daddy stood to greet me.  He was huge!  A total hunk.  I could see other ladies in the restaurant look over with jealousy as he embraced me.  He was 6 foot four of muscle.  He wore a tight white shirt and black leather trousers.  He bent down and gave me a firm kiss on the lips his tongue darting powerfully between my soft red lips.  I gasped as he let me go.  I’d never encountered such a specimen of masculinity and realised that my sissification was to get a lot deeper than I ever feared possible.  I thought I’d have a quick bite to eat and be walking home with Isobel in an hour or so, her aim of a little public humiliation realised.  But now I understood that Daddy intended to get things to a physical level as soon as possible.  As I tried to compose myself Isobel was grinning broadly at a table adjacent to ours.  Her camera was out and I knew she’d be taking photos and videos as she loved to do.

I barely remember the details of lunch.  Daddy ordered for me, a salad for me while he had a rare steak.  He held my hand over the table, complimented me on outfit, stroked my cheek, and kissed my hand.  I was feeling kind of scared but also, to my horror, kind of enjoying the attention.  Then I got a text on my phone.  It was from Isobel.  “Slip off one of your sandals.  Say your leg is a little stiff and then place it in Daddy’s crotch.  Give 3 squeezes with your toes and put your heel back on.  If you don’t do it I will leave you with Daddy for the rest of the week.”  I closed my eyes, composed myself, and did exactly as she said.  His bulge felt huge under my tiny feet.  Daddy gave me a wicked smile.  Isobel actually giggled and I saw her put her camera down after filming it.  He ordered dessert, a slice of chocolate cake and two forks.  Isobel texted again, “Meet me in the ladies room.”  I excused myself and followed her through the packed restaurant so self-conscious as I was quite sexily dressed for lunch.  I passed a couple of tables of guys and they all looked up as I passed.

Once in the bathroom Isobel hustled me into a cubicle.  “Oh my!” she

beamed.  “This is going so much better than I expected!  He is such a hunk!  It’s wonderful to watch a real man take control of my feminized ex – and in such a public way too.  I don’t know about you but I’m really enjoying this.  You’re doing so well I’ve something for you if you like.”  I didn’t know what to expect but then she pulled out a pair of breastforms from her bag!  “They’re  36C breasts, nice and eyecatching.”  “But…,” I stammered, “I’m used to my flat chest today, everybody will notice if I have big breasts now.”  “Don’t be silly hun, you really wanted them this morning.  And think, once you leave the restaurant in a few minutes you’ll look so much more feminine with breasts.  Come on hun, you do want them don’t you?”  I was unsure but Isobel was very convincing and she knew how to use her good looks to manipulate my male side.  “Okay, put them on me then.”  “Wonderful!  You will look soooo hot!”  Isobel glued the breastforms on, held them in place until they were set and pulled my dress up.  “Oh wow!  They look amazing!  You have incredible breasts, every girl is going to be jealous and every guy hard!”  I blushed like the girl I was becoming.

Then, to my utter horror, Isobel reached for my wig and began to remove it.  “What are you doing?” I said in a panicked voice.  “Why sweetie, remember what Daddy instructed?  You may wear breastforms or your wig but not both.  And now that you’ve decided to wear a nice big pair of bimbo breasts I’ve to remove your wig or else Daddy will be very angry.”  I was close to tears.  “But everybody will definitely know I’m  a sissy now!”  “Oh sweetie, I’m sure everybody won’t notice that you look a little more…androgynous.”  “I’ll take the breasts off and put the wig back on,” I said defiantly.  “I’d really love to help you sweetie but they’re glued on solidly now.  You’re such a bimbo.  You should have thought of this before asking for some cleavage.”  As Isobel was speaking she took a small bag, it looked like chainmail, from her handbag, dropped the wig in it and locked it with a padlock.  “Don’t worry hun you won’t have to think about the wig again today as the key to this padlock is back at home.”  She also quickly took a polka dot hairband with a bow on it and set it on my male head of hair.  “There sweetie, you look delightful, the kind of vulnerable femboy look that Daddy loves!”

She swung open the cubicle door.  I was horrified to see myself in the mirror.  I had gone from passable to an obvious femboy, the slightly more masculine angles of my dolled up face were no longer softened by my wig.  “Oh fuck!” I moaned.  “Chastity! That’s no way for a girl to talk,” she said with obvious delight at my predicament.  Just then the bathroom door opened and two females walked in.  They looked like twentysomething office girls in pencil skirts, sexy blouses, and high heels.  These weren’t secretaries, they carried the air of confident bosses.  They looked at me, looked at each other, and smiled with delighted intrigue.  “Well don’t you look like a doll honey!” teased the blonde.  “What’s your name pretty?” said the brunette in a taunting manner while Isobel looked on.  “Chastity,” I whispered.  “How wonderful,” said the blonde, “you look like such a doll.”  I was blushing furiously.  “He used to me my ex-boyfriend,” explained Isobel, “until I found out he was cheating on me.  Luckily it was the same time I found out about his fetish for panties and high heels so I’d the perfect blackmail material.  Now he’s locked in chastity 24/7 and is on his first date with a guy today.”  “That’s soooo fucking hot,” exclaimed the blonde, “I bet his boyfriend will have lots of fun with his new toy!  Let’s take some photos together.  I want to post them on Facebook.”  So we all took photos together with me blushing uncontrollably.  I walked back to my date, Isobel close behind me to see the reaction of the customers to my changed appearance.  My cleavage swayed before me as I walked shamefacedly back to Daddy.  My heels clicked loudly in as the restaurant hushed as all eyes watched a feminized femboy blush his way back to his hunky master.  There were a couple of, “Oh my God!” and “Is that a guy!” as I took my seat.  Daddy was smiling serenely as I took my seat opposite him and crossed my legs.  “You’re such a doll, Chastity.  I hope you realise how much of turn on you are.  I’ve always wanted a totally humiliated and feminized fucktoy and it looks like I’ve found one.”  The chocolate cake was on the table and he began to feed me a piece.  I returned the favour by now totally crushed by my experience I was playing the part of a smitten young miss desperate to please her man.  He put some cake on his finger and thrust it towards me just as the maitre d’ arrived, presumably to ask how everything was.  I knew what to do, so in full view of the maitre d’, my ex-girlfriend, surrounding customers, and to any passing people, I opened my soft red lips and slid them over Daddy’s finger licking and sucking at the gooey cake.  Daddy pumped it into me a couple of times and I caressed it with my tongue.  I had reached a stage where my only hope to avoid total public humiliation was for Daddy to take me back to his place straight after the restaurant.  But Daddy had other plans…

In the second and final part Daddy decides Chastity deserves a present before he takes his femboy home…

Please comment if you’d like to read part 2.