Just a Closet Sissy Boy Age 37

I know I have been bugging you for a while now to let me dress you up as see what you’d look like as a girl.  I’m doing some pre-planning and have some great ideas for Halloween costumes if you’d agree to them but first I have to see if I can achieve a look that will fit.  Thank you so much for agreeing to let me do this to you, you’ve been such a good sport about it.  I started getting some ideas when you asked me to help shave you down before your last swim meet and I realized as I was helping you that with your slender body, long legs and a bit of makeup we may be able to compete in the big Halloween contest that they hold downtown and actually have a chance at winning.  This is a perfect day to experiment as your swim meet was yesterday and its pouring rain and we don’t have any plans to go anywhere.

I’m kind of thinking about a take off from Star Wars with you as a princess and me as some sort of Chubaca character.  So now that I have you dressed why don’t you let me take some pictures of you in various poses so we can decide if this works or not.  That’s it lay out on the floor and smirk a bit like you are trying to entice someone. If we are ever going to have a shot at winning that contest we’ll both have to learn to act talk like the opposite sex.  See if you can raide your voice a bit and say something like “Do you like what you see big guy?”  

Ok lets try another picture.

Life your leg so and tilt to the opposite side so you show a good bit of bare leg and a lot of skin on your back and arm.  Try putting your right hand against your face and make believe you are waiting for someone to come over to you (aren’t you glad I dabble in photography - LOL).  That’s great wait until you see it you really look sexy.  Now try saying something in your girly voice like “I’m waiting big guy, lets have some fun.”

You are doing pretty good with the voice by Halloween it will be perfect.  Ok lets try another picture shall we?  This time though no laying down on the job you’ll have to stand up and turn so I can see your back.

Ok great now place your hands on your hips and bend your left leg at the knee so it tilts your hips.  My oh my you are a natural, wait until you see this shot.  If I didn’t know I had dressed you in this outfit I would swear you are a girl. You really look sexy.  Now lets try something a bit different.  Instead of me telling you what to say you tell me in your own words using your girly voice how much a girl loves to receive attention from big strong men.  Remember if we enter that contest one event will require us to role play our costumed parts for two minutes so you will have to dialogue but for a grand prize of $5,000 it will be worth it won’t it?  Ok go ahead and try being seductive.  

Wow I didn’t know what to expect but you did a great job considering this was on the fly.  Ok give me a couple of minutes while I go in a put a composite of the photos I took together to show you.  No you just relax out here a bit I really want to show you how great you look.

Ok I’m back.  I’ve rigged this up so it will play on the TV.  Come sit next to me and let me know what you think.  Oh I have a bit of a surprise for you, first we’ll start with some still pictures so you can appreciate how good you look and then I will show you the video I put together.  I didn’t tell you I was videoing this because I didn’t want to make you nervous trying to pose and speak but you did great. (Pictures start playing and they are both laughing and commenting on how good he looks.  Then the video starts and he sees himself posing as asking for attention from real men)

What’s wrong sweetie you are squirming around like you are very nervous.  I told you that you’d make a very sexy girl and as you can see you really do.  What I didn’t tell you is that I found out about you cheating on me with that little blonde on the girls swim team.  Now if you don’t want these pictures to be seen by anyone but us you will take one more set of pictures.

That’s right get down on your knees and make love to that dildo licking and sucking it and then use your cute girly voice to tell people how you want to be a slut and have real cocks in your mouth and your sissy boy clitty.  That’s it keep sucking and talking unless you want me to send your pictures to your little blonde.  Good sissy boy.  Now I will keep you as my boyfriend but with a few changes.  

First we are going to lock up your clitty and it will only be unlocked  when I want you.  Second you will go into the bedroom and remove all of your male underwear and we will go to the mall to buy you some nice sexy panties which you will wear all the time.  Third you will start having your body waxed completely at a salon I know every five to six weeks.  They won’t wax your head obviously but they will remove all other body hair other than what is left when they are done shaping and arching your eyebrows.  Fourth you will wear clear nail polish on your fingers and toes all them time and you will paint your nails in front of me.  I think with those changes its a safe bet you won’t be two timing me anymore.  However if you screw up you can be sure your pictures will be all over the campus on all kinds of media.  And if you screw up I will release your video on to the internet and send links to all of your friends either privately or publicly.  In short I now own your sissy ass and you will do things my way and my way only. 

Photo credit - @sdsissyboy

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I know I have been bugging you for a while now to let me dress you up as see what you’d look like as a girl.  I’m doing some pre-planning and have some great ideas for Halloween costumes if you’d agree to them but first I have to see if I can achieve a look that will fit.  Thank you so much for agreeing to let me do this to you, you’ve been such a good sport about it.  I started getting some ideas when you asked me to help shave you down before your last swim meet and I realized as I was helping you that with your slender body, long legs and a bit of makeup we may be able to compete in the big Halloween contest that they hold downtown and actually have a chance at winning.  This is a perfect day to experiment as your swim meet was yesterday and its pouring rain and we don’t have any plans to go anywhere.

I’m kind of thinking about a take off from Star Wars with you as a princess and me as some sort of Chubaca character.  So now that I have you dressed why don’t you let me take some pictures of you in various poses so we can decide if this works or not.  That’s it lay out on the floor and smirk a bit like you are trying to entice someone. If we are ever going to have a shot at winning that contest we’ll both have to learn to act talk like the opposite sex.  See if you can raide your voice a bit and say something like “Do you like what you see big guy?”  

Ok lets try another picture.

Life your leg so and tilt to the opposite side so you show a good bit of bare leg and a lot of skin on your back and arm.  Try putting your right hand against your face and make believe you are waiting for someone to come over to you (aren’t you glad I dabble in photography - LOL).  That’s great wait until you see it you really look sexy.  Now try saying something in your girly voice like “I’m waiting big guy, lets have some fun.”

You are doing pretty good with the voice by Halloween it will be perfect.  Ok lets try another picture shall we?  This time though no laying down on the job you’ll have to stand up and turn so I can see your back.

Ok great now place your hands on your hips and bend your left leg at the knee so it tilts your hips.  My oh my you are a natural, wait until you see this shot.  If I didn’t know I had dressed you in this outfit I would swear you are a girl. You really look sexy.  Now lets try something a bit different.  Instead of me telling you what to say you tell me in your own words using your girly voice how much a girl loves to receive attention from big strong men.  Remember if we enter that contest one event will require us to role play our costumed parts for two minutes so you will have to dialogue but for a grand prize of $5,000 it will be worth it won’t it?  Ok go ahead and try being seductive.  

Wow I didn’t know what to expect but you did a great job considering this was on the fly.  Ok give me a couple of minutes while I go in a put a composite of the photos I took together to show you.  No you just relax out here a bit I really want to show you how great you look.

Ok I’m back.  I’ve rigged this up so it will play on the TV.  Come sit next to me and let me know what you think.  Oh I have a bit of a surprise for you, first we’ll start with some still pictures so you can appreciate how good you look and then I will show you the video I put together.  I didn’t tell you I was videoing this because I didn’t want to make you nervous trying to pose and speak but you did great. (Pictures start playing and they are both laughing and commenting on how good he looks.  Then the video starts and he sees himself posing as asking for attention from real men)

What’s wrong sweetie you are squirming around like you are very nervous.  I told you that you’d make a very sexy girl and as you can see you really do.  What I didn’t tell you is that I found out about you cheating on me with that little blonde on the girls swim team.  Now if you don’t want these pictures to be seen by anyone but us you will take one more set of pictures.

That’s right get down on your knees and make love to that dildo licking and sucking it and then use your cute girly voice to tell people how you want to be a slut and have real cocks in your mouth and your sissy boy clitty.  That’s it keep sucking and talking unless you want me to send your pictures to your little blonde.  Good sissy boy.  Now I will keep you as my boyfriend but with a few changes.  

First we are going to lock up your clitty and it will only be unlocked  when I want you.  Second you will go into the bedroom and remove all of your male underwear and we will go to the mall to buy you some nice sexy panties which you will wear all the time.  Third you will start having your body waxed completely at a salon I know every five to six weeks.  They won’t wax your head obviously but they will remove all other body hair other than what is left when they are done shaping and arching your eyebrows.  Fourth you will wear clear nail polish on your fingers and toes all them time and you will paint your nails in front of me.  I think with those changes its a safe bet you won’t be two timing me anymore.  However if you screw up you can be sure your pictures will be all over the campus on all kinds of media.  And if you screw up I will release your video on to the internet and send links to all of your friends either privately or publicly.  In short I now own your sissy ass and you will do things my way and my way only. 

Photo credit - @sdsissyboy