Please encourage the author through your comments and star ratings for this story!
Story Credit: Jinal
For more reader contributed stories, click here.
I had a fantasy for dressing up since puberty hit me. I wanted to crossdress even before I knew what it meant. I always dreamt of wearing sexy feminine clothes. I could never try any female clothes at that time though, but the curiosity in me never died.
When I started dating my wife, I once gathered the courage and told her my fantasy. I am sure she did not expect that and was rather surprised by the fantasy, but she said she will help me live it once and if she found it comfortable, we will see where can we take it further. Once while we were making out, she took off her bra and asked me to try it on. I was really excited and tried it on myself. While I had mixed feelings of excitement and embarrassment, she could not stop from giving the disgusted look. I took it off immediately and told her I did not like the idea, just to save her from giving the difficult message that she did not like it.
I did not discuss that idea with her for next 10 years. We got married and led a very happy life. But the thoughts of wearing feminine clothes never went away. In fact living with her and looking at her in the sexy clothes from time to time increased the desire of wearing her clothes. I had even tried her clothes in her absence. But everytime I thought of bringing that topic, that looks on her face when she saw me reminded me of not doing it.
Things did not change for 10 years. But then one incident changed my entire life. My wife had gone out of town for 10 days. She wanted me to buy her a gift when she came back. I jokingly said that I can gift her sexy lingerie if she wants (now I never bought lingerie for her before and so this was new for both of us). I thought she will not like the idea, but she infact encouraged me to buy for her.
She loved my choices and we had one of the best sex that night. And so it was decided that only I will buy lingerie for her from there on. She started to discuss her likes and dislikes with me about her clothes. She would wear them and explain me what exactly does she like in it and what is not comfortable.
I was getting the two best things – the sex life got better and I could see her in my choices of lingerie;
I started getting more daring with my choices and the sluttiness in each of my selection started increasing. Once the bra that I bought for was really slutty and gave her a look of a hooker. It was really a small one and hardly covered anything. She would otherwise always try the clothes that I would select but this time she got really agitated. She threw it away and asked me not to bring such clothes for her. I really wanted her to try it on and started requesting her to atleast try it once. “You can be my whore for one night right?” I told her. Thinking that she might like the idea.
Instead, she got even angrier with that and told me “Why dont you become a whore for a night then? I have had enough of parading for you. Why dont you try to dress up for me once?”
I had no idea whether it was her anger speaking or was she really suggesting that. I was not even sure whether she remembered by fantasy.
While I was in my thoughts, she asked me again “I am waiting. Try it on and show me.”This time the looks on her face suggested I should actually try it.
I started removing my clothes to try the bra. removed my shirt and then started removing my shorts. She said “Wow, getting naked just to try on a bra, you really are my whore”.
I needed no further encouragement. My dick was eagerly waiting to get free. I got naked and put on the bra. Now I am really hairy and rarely shave, so I am sure I would be looking ridiculous. But this time her expressions were different. She was eyeing me with lust.
As soon as I wore the bra, she went to her wardrobe and took out some other clothes. First of all,
she gave me a pair of pads from one of her other bra. She also gave me thongs to wear with it. Now I
had tried her panties but never tried her thongs. I asked whether I can wear my boxers below.
“Did I ask your opinion? Just do as I say” Suddenly the roleplaying game was turning from her being the hooker to me being her submissive lesbian partner.
I quietly wore the thongs. It did not cover anything. My dick was too big to hide behind the small help and the material was causing irritation in my ass. Looking at my discomfort, she suddenly pulled me towards herself and told me “Now you will understand what I go through to entertain you.” and then whispered “And looking at your dick, I am sure you are enjoying it more than me”.
With that she went and sat on the bed. I was too shocked to move. She got comfortable and called me nearer “Come here honey. Lets see what have you got there”
“Sure mam” I was not sure why I called her mam. I simply followed what I was asked to do.
“Yes, ‘mam’ would be nice. I like you calling me mam, dressed up like that” and with that she pulled me nearer and gave me a long kiss. Her fingers started exploring my entire body. She squeezed my ass and bite my lips at the same time. All I could manage was a soft moan.
Finally I gathered some sense and realised that she was still fully clothed. I tried unbuttoning her shirt, but she stopped me right there with a firm grip on my hand.
“Did I tell you to remove my clothes? Don’t act smart missy, it might not be good for you” She said with a stern look on her face. I did not dare to do anything that she did not want from there on.
She pushed me on the bed and started kissing me all over my body. She started kissing and sucking my fake boobs as well. The feeling of making love to her as a girl was overwhelming. I was enjoying every kiss of her and letting out moans.
“My missy is liking it I think. Do you like being my girl?” “Hmmm”
“You will have to say it, missy” “Yes I love being your missy”
As soon as I said that, she bit me on my chest just above my bra, as if biting my boobs. I was actually feeling like being a girl and getting turned on by her playing with my boobs.
Then she pulled the thongs aside and started kissing my dick. That caused the thongs to go inside my ass and made it even more uncomfortable for me. I tried adjusting it but she stopped me.
“Didn’t I tell you not to do anything without my permission? I want my missy to enjoy a little penetration in her ass too”
She started kissing my dick and taking it in her mouth. She had never taken my dick in her mouth without condom earlier, but the domination over me probably made her do it for the first time. She deliberately pulled the thongs along with sucking my dick. I started to enjoy the feeling in my ass and
“Don’t just lie there missy, your boobs need your attention. Press them for me.”
I did as I was told. Started squeezing my boobs and enjoyed getting sucked. I could not hold for longer and came rather quickly that day.
Once I was done, she came on top of me and hugged me tightly. I tried to move away after a while, to change the clothes.
“Where do you think you are going missy?”
“I thought I will change the clothes before sleeping”
“Did I ask you to change? Didn’t I tell you to do only what is told to you?” She said with a smile and gave me another hug. “I want you to be my girl for entire night. And I know you like it to. So be my cute little whore for the night and sleep like this”
I slept in those clothes for entire night with her teasing me from time to time. She would often woke up and press my boobs or my dick. I must say it was an experience which was better than any other earlier experience. I knew I would enjoy women’s clothes but never knew I would enjoy it so much.
Next day started as usual. We got ready and went to work. I was getting confused whether it was for a night or it may continue and just about then, I got a text from her saying “From now on, you can buy my lingerie and I will buy yours”.
And that is how it started. I would buy sexy lingerie for her and she would wear it for me. She would sometimes buy lingerie for me and make me her missy for that night.
I started shaving my body to look and feel more like a girl. I usually wear full sleeves shirts to work and hence no one in the office could notice the missing hairs. I had to wear shirts and trousers even when I was with friends to hide my shaved arms and legs.
She would assume the dominant position while I would be the girl. I enjoyed being the submissive girl in the relationship.
Then one day, she texted me saying “I have changed the trend a little. I have bought gifts for both of us for tonight.”.
I thought she would have bought lingerie for both of us that day. I went home early that day and started preparing for the night. I took a proper bath and shaved my face, arms and legs. I wore her bathrobe and came out of the bathroom when she entered the room.
“Wow, my missy is too eager for the night” She came close and gave me a kiss. Her dominance became very obvious with the way she kissed me. As such I knew how she behaves but something looked different that day. She was behaving more bossy than ever.
“Prepare the dinner while I get ready. Don’t take too much time. And no need to wear clothes”
I did as I was told. The anticipation for the night was too exciting for me. She came down for dinner after sometime. I was expecting her to wear something special, but she was wearing a normal shirt and pyjama for the night. I was not able to understand the selection of clothes but had understood by then not to question her anything.
Our game of dominance never left our bedroom, but that day, she was behaving bossy even in the kitchen for the first time. When we were done with the dinner, she said “Do the dishes and come upstairs missy. Don’t be late, you will not like the consequences” By saying that she gave me a kiss, squeezed my dick and went upstairs.
When I went upstairs, my gift was lying on my bed. The sluttiest possible bra with matching thongs. She was sitting on the working desk as if least interest in me. She asked me to get inside the bathroom and get ready. I went inside and put on my pads along with the bra and thongs. I had learnt how to apply a little make up by then and decided to try it on. Once done, I saw myself in the mirror and saw the sexiest version of me possible.
I went out and saw that she was still on the working desk, reading a magazine. As soon as she saw me, a smile came on her face, but she soon changed her expressions and called me near her.
“Come and sit here missy” She asked me to sit on her lap. “May I ask mam when will she wear her gift for the night?”
“You have no right to ask anything missy, but for your information I am already wearing it”
I sensed that something was odd and that she had planned the entire night. So I just went with the flow. I went and sat on her lap. She started talking to me while moving her hands on my bare back and thighs.
“You know missy, as much as I like being the dominant person in the relationship, I do not see myself as a lesbian. I think there is a need of a man in our relation”.
This shocked me to the core. While I loved dressing up, I was not gay and never wanted to be with a guy.
“But honey I don’t think I will be comfortable with that. This dressing up is only for you. I do not want anyone else to know it. A man would be the last person I would want to know.”
“Did I ask your choice missy?” and with that she squeezed my boobs. “I have invited a man tonight and you are the slut who will entertain him”
Now I was getting really scared. I gave her a kiss and told her with a request “Please mam. I do not want anyone else in the room. Please don’t make me do that.”
“Who said there will be someone else, missy?” And with that she took my hand in hers and guided it to her crotch. It was then that I felt a big strap on. That was the special gift for her for the night. She had already worn it while getting ready.
“I want to be the man in the relationship. Please be my bitch for the night. I love making you my bitch” She said kissing me and caressing my boobs.
I was not sure how to react. I had never thought of this scenario. But then I wanted to be a part of her fantasy as she had been part of mine. So I simply went with the flow.
“So, do this man have a name?” I said with a smile and kissing her back. “Its master for you, bitch” She bit my lips
She made me stand up and turn. She gave two playful slaps on my butts. I wiggled my butts for her to enjoy the view. She then stood up and ordered
“Help me take out my clothes bitch. I need to get relaxed”.
I took out all her clothes and then I saw it. An 8 inch dildo with thickness even more than mine. Looking at my face, she understood what was going on in my mind. “It wont hurt if you make love to
it” She said, pushing me on my knees.
Reluctantly, I went down on my knees and started kissing the dildo. I held it with my hands and started taking the tip in my mouth. It was then that I realised that it was a two way dildo and a part of it was inside her as well. Her juices were already flowing and the smell made me lusty.
I forgot the reluctance and started enjoying it. I slowly took it in my mouth and started sucking it.
“I knew a slut like you would be a natural sucker” She said with a smile. I smiled back. I knew I had become the girl in the relationship. And more than that, she was the man now.
She pulled me up and pushed me on the bed, almost throwing me. She started kissing me passionately all over, all the time talking to me like a girl.
After exploring my entire body, she removed my thong and made me sleep on my chest. She slowly came near my ears and whispered “Ready to lose your virginity to your master, bitch?”
I had never thought of getting pegged, but it seemed very natural in that moment. “Yes master. Fuck me please”
“That’s like my girl. I knew you would like it.”
She applied some lube on my ass and slowly inserted the dildo. It was too much at first for me, but she really took it slow for me. After a couple of strokes, I started to enjoy it and my body got relaxed. Just when I was starting to enjoy, she stopped.
“What happened, master?” I asked
“I think my bitch is liking it” “Yes I am”
“In that case you need to ask for it if you want more”
“Please fuck me master. Make me your bitch. I want you to fuck my ass. Please” “With pleasure, bitch”
And the next stroke was not gentle. The pain and pleasure took me in a different world. I lost the
track of the time how long she fucked me. I never imagined cumming while getting my ass fucked. My hands naturally started caressing my boobs for pleasure. She came after a long time of fucking and then simply fell on me and slept. We slept there for a while before coming to senses. As soon as she woke up, she fucked me again, without even asking me. I felt like her fuck toy, which was making the sex more pleasurable for me as well.
And that night changed everything. From there on, we have never made sex as lesbians. It is either her as a girl or me as her bitch. She has started becoming dominant even when she is the girl in the room. And I am not complaining about it.
If you liked this story, please don’t forget to write the comments for the author!
For more reader contributed stories, click here.