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maxfun791 45 / M
"Looking for a Sissy to dress up"
Braintree, Massachusetts, United States
 
Standard Member
Last Visit: More than 3 months
Member Since: August 16, 2022

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maxfun791 45/M
Braintree, Massachusetts
Introduction
I am looking for someone who wants to dress up in panties, lingerie, heels, lipstick and a maybe a wig. If you are new to this, I will purchase everything. Ideally, I would also like to find someone who wants to roleplay (cop/prisoner or blackmail type of scenario). I am on the dominant side and love ass slapping doggy style sex. I am extremely discrete and expect the same. Drug, disease free, and otherwise "normal" guy here looking for another with the same kink. Not looking for many people, just to find one steady FWB. If this interests you and you are turned on, message me Free members can contact me. Picture this sort of roleplay... We are roommates, both straight males. You have had a secret obsession with crossdressing for a while, and decide to order some lingerie, heels, wig, etc. I travel often so you decide that you will get all dolled up one night that I am out of town. One night, I leave for a business trip. As soon as I leave, you grab your outfit and put it on. You go into the bathroom, and start putting on your wig and lipstick to check yourself out in the mirror. You are feeling feminine and sexy. As you turn to check out yourself in the mirror, you are horrified to see me standing in the doorway. You ask "what are you doing back, I thought you left" and I reply "I forgot my wallet, what are YOU doing"? You do your best to convince me that this is just a joke, and you are trying on an outfit for Halloween. I laugh and say "ok whatever" and you try to run into your bedroom but I step in front of the doorway. You say "please, dont tell anyone, this is super embarrassing. I am not gay or anything". I reply "Yeah, I dont buy it. Nobody dresses in this stuff just for a costume" and I run my hand up your thigh highs and pull the elastic part of your thong and snap it back. I then say "dont worry I wont tell anyone" You feel an overwhelming sense of relief and walk to the bedroom and sit on the corner of your bed. You turn your head around and realize I followed you into your bedroom. I walk right up in front of you and say "I wont tell anyone you like to dress as long as you dont tell anyone you sucked my cock" I start rubbing my cock over my pants and you see that I have a rock hard erection. You realize at this point what you have to do and I put my hand on your shoulder and guide you on to your knees. I unzip my pants and pull out my hard cock. You look up and open your mouth, slowly placing my cock on your tongue. At first I let you explore my cock with your mouth, let you get used to it. After a few minutes, you ask me "are you going to cum soon"? I then start to tell you how I like my cock sucked, and teach you how to be a good little slut. I tell you im about to come, and you tilt your head back and I explode all over your face. At last, you are relieved, it is over. You liked doing it but you will never admit it to me. You get up and go to the bathroom to wash your face off. After a few minutes you come back to the bedroom to get changed back to your normal clothes. As you walk in, you ask "what are you still doing here" and I reply "well, that was the first part of the deal, now comes the other part" You are horrified now, you think what's next? I walk up to you, put my hands behind you and start to caress and squeeze your ass. I turn you around and guide you onto the bed, and I tell you to put your ass in the air. I pull your thong aside to get a look at your tight little ass, and all of a sudden you feel my tongue start flickering your ass. As I am doing this, you feel me grab your hard cock while I am flicking my tongue on your ass, and you realize that your are turned on. I notice it, and say "I knew you would like being my bitch, we are going to have to make a regular thing of this". At that point, I have gotten behind you and you can feel me slapping and rubbing my cock on your tight hole. As I start to slide it in, you tense up and I slap your ass unexpectedly. You gasp and let out a sign that you like it. If you are turned on by now, we should talk. Message me.

My Ideal Person Picture this sort of roleplay...

We are roommates, both straight males. You have had a secret obsession with crossdressing for a while, and decide to order some lingerie, heels, wig, etc. I travel often so you decide that you will get all dolled up one night that I am out of town. One night, I leave for a business trip. As soon as I leave, you grab your outfit and put it on. You go into the bathroom, and start putting on your wig and lipstick to check yourself out in the mirror. You are feeling feminine and sexy. As you turn to check out yourself in the mirror, you are horrified to see me standing in the doorway. You ask "what are you doing back, I thought you left" and I reply "I forgot my wallet, what are YOU doing"?

You do your best to convince me that this is just a joke, and you are trying on an outfit for Halloween. I laugh and say "ok whatever" and you try to run into your bedroom but I step in front of the doorway. You say "please, dont tell anyone, this is super embarrassing. I am not gay or anything". I reply "Yeah, I dont buy it. Nobody dresses in this stuff just for a costume" and I run my hand up your thigh highs and pull the elastic part of your thong and snap it back. I then say "dont worry I wont tell anyone" You feel an overwhelming sense of relief and walk to the bedroom and sit on the corner of your bed. You turn your head around and realize I followed you into your bedroom. I walk right up in front of you and say "I wont tell anyone you like to dress as long as you dont tell anyone you sucked my cock" I start rubbing my cock over my pants and you see that I have a rock hard erection. You realize at this point what you have to do and I put my hand on your shoulder and guide you on to your knees. I unzip my pants and pull out my hard cock. You look up and open your mouth, slowly placing my cock on your tongue. At first I let you explore my cock with your mouth, let you get used to it. After a few minutes, you ask me "are you going to cum soon"? I then start to tell you how I like my cock sucked, and teach you how to be a good little slut. I tell you im about to come, and you tilt your head back and I explode all over your face. At last, you are relieved, it is over. You liked doing it but you will never admit it to me. You get up and go to the bathroom to wash your face off. After a few minutes you come back to the bedroom to get changed back to your normal clothes.

As you walk in, you ask "what are you still doing here" and I reply "well, that was the first part of the deal, now comes the other part" You are horrified now, you think what's next? I walk up to you, put my hands behind you and start to caress and squeeze your ass. I turn you around and guide you onto the bed, and I tell you to put your ass in the air. I pull your thong aside to get a look at your tight little ass, and all of a sudden you feel my tongue start flickering your ass. As I am doing this, you feel me grab your hard cock while I am flicking my tongue on your ass, and you realize that your are turned on. I notice it, and say "I knew you would like being my bitch, we are going to have to make a regular thing of this". At that point, I have gotten behind you and you can feel me slapping and rubbing my cock on your tight hole. As I start to slide it in, you tense up and I slap your ass unexpectedly. You gasp and let out a sign that you like it.

If you are turned on by now, we should talk. Message me.

Information
  • 45 / male
  • Braintree, Massachusetts, United States
Sexual Orientation:
Prefer not to say
Looking For:  Men or Trans
Birthdate: January 1, 1979
Height: 6 ft 1 in / 185-187 cm
Body Type: A little extra padding
Race: Caucasian
Male Endowment: Average/Average
Circumcised: Prefer not to say
Speaks: English
Glasses or Contacts: Contacts