- Gay Stories -
Straight Male / 28
From a young age I had a fascination for women's lingerie. The look and feel were so feminine and sexy I would imagine myself wearing it and feeling as good as the models showing it off.
At around 13-14 I found a pair of lace boyshorts and hold-up stockings in a draw at a friend's house due to my inability to stop myself snooping.
I would wear them at night feeling sexy and turned on as the material would strain against my cock and the stockings would run against my bed sheets this continued for many years until I turned 19 and moved in with my long term girlfriend.
I once told her about my love of lingerie which she accepted but didn't like the idea of me wearing it . I stopped wearing any lingerie during this relationship until 4 years later when I met my now wife.
She loved to dress up and would use any opportunity to do so which I would never complain with. One night she caught me wearing a pair of her lace panties and instead of flying of the handle so to say she calmly asked how long I had been wearing them and why.
Satisfied with my answer she would then day by day tease me more and more during sex about my love of lingerie, often commenting on how much harder my cock would be as she teased me about wearing her panties and hold-up stockings.
One night before bed she produced a pair of open toe black high heel shoes, a pair of black lace boyshorts and a pair of black hold-up stockings complete with red bow and red seam. I commented on how sexy she was going to look in them before she informed me I would be wearing them for the night.
Slightly embarrassed and without much arguement I shyly slipped into the clothes she handed me and quickly hid in bed where she joined me. Running her hands up my legs making me release a noise I couldn't describe from my lips.
Feeling happy with herself she moved her hand to my now painfully erect cock feeling my precum through the fabric and teased me about how turned on I was dressed like a slut.
Needless to say that night I fucked her longer and hard than I was ever able to before and never remembered falling asleep instead waking up the next morning still in my panties stockings and heels. Feeling embarrassed I quickly undressed and avoided the situation for a while.
One night she text me to let me know she would not be coming home due to her being severely drunk. I took the opportunity to dress back in the black slutty clothes she had made me wear and laid in bed running my hands over my lingerie and feeling extremely sexy.
Not wanting to ruin the outfit I slipped my feet into my black sexy heels and tried my best to navigate our small flat. This only turned me on more as I felt the cool air against my stocking clad legs and loving the feeling of my panties against my skin.
Feeling brave I started to rummage through my partner's drawers in search of more panties only to find the dildo I had purchased for her. Suddenly I was caught by a wave of thoughts and found myself staring at this flesh coloured "monster".
Up till this point I had never had one single thought of ever penetrating myself or being penetrated by anything, but standing there in my lingerie and heels holding her dildo I found myself wanting to feel what a woman felt whilst they moan in exctasy.
Finding the lube I used to fulfill her anal fantasy's previously I applied a generous amount to her 8" dildo with was generously girthy and began rubbing my asshole with it, enjoying the feeling of this cock at my asshole I pushed gently and remember the pain as the head slipped inside me catching me off guard and causing me to clamp down on it.
Once I had calmed down I began to enjoy the feeling of this thing inside me despite feeling shame at the idea of being dressed in lingerie taking a dildo to the ass, needless to say I was soon struggling to fit her dildo inside me and was relieved once I had managed to lower myself down it's entire length.
I came harder than I very had and could feel myself clamping down on the thick long dildo in my ass, feeling empty as I pulled it from my ass and proceeded to clean it not wanting my partner to find out.
Unfortunately I did not have the smart idea to remove the items of lingerie I had been wearing and was caught in the morning by my partner. With a little encouragement she convinced me that it was just a link of mine and was happy to let me wear any of her lingerie whenever I wanted , which was handy due to us both being on the shorter side and both being roughly a size 14 I jumped at the opportunity.
Regularly wearing stockings panties and heels around the apartment I began to feel more and more feminine and as sexy as I viewed the models who drew me to the life of wearing lingerie till one night my partner introduced the idea of pegging me.
Upon hearing this it was very hard to hide the raging hard on that had been growing under my lace boyshorts of which she noticed, at this point she knew the idea turned me on and had already begun sifting through her draws producing the dildo I had previously met and had continued to play with any chance I was alone.
She had me lay on my stomach and placed a pillow under my pelvis to raise my ass slightly making it stick out slightly she commented on how good my ass locked in her panties before telling me to remove them so she could slip a thong on me. Feeling my ass cheeks spread slightly she placed the thing string against my ass as she began reading my stocking clad legs running her hands to my heels back up my thighs to my ass cheeks.
I could feel my asshole opening slightly as she press my ass cheeks and tried to hide me excitement as much as possible. I heard her grab the bottle of lube and felt her hand remove the thong string from covering my asshole leaving me exposed as she poured lube all over my ass and asshole rubbing and grabbing my ass, she spread some of the lube into my asshole and set to work lubing up my secret friend.
A moan escaped my lips as she gently pushed the dildo against my asshole which by now was very accustomed to her 8inch dildo, groaning as with little effort she was able to push her dildo deep inside me.
She commented on how horny I must have been as I took her large dildo so easily something she was not easily able to do in her ass. Which then embarrassingly I confessed of my solo play sessions giving great detail as to how I would sit on her dildo pushing down as hard as I could to feel it push deep inside me.
To my suprise she was not angry but instead told me that watching me take her dildo was the sexiest thing she had ever witnessed and made me feel the wet spot she had left under her pussy. Shamefully I asked her to continue and felt her withdraw the entire dildo from my ass before ramming it deep inside me again smiling wickedly as she made me moan.
She took full control of the situation and had her dildo ramming repeatedly deep inside me making me take it like I had given her so many times till I begged her to allow me to fuck her and release the frustration I had built up.
She made me remain wearing my lingerie and heels and began questioning me as to whether or not I was gay to which I replied no I just enjoyed the feeling of anal stimulation.
Feeling she accepted my explanation i attempted to remove my lingerie to which she told me sternly no as she enjoyed me wearing feminine lingerie, this led to me wearing some form of lingerie nightly to bed and around the apartment so she could comment on how good my ass and legs looked. The comments had no started to become more regular and she ..(continue confession)
At around 13-14 I found a pair of lace boyshorts and hold-up stockings in a draw at a friend's house due to my inability to stop myself snooping.
I would wear them at night feeling sexy and turned on as the material would strain against my cock and the stockings would run against my bed sheets this continued for many years until I turned 19 and moved in with my long term girlfriend.
I once told her about my love of lingerie which she accepted but didn't like the idea of me wearing it . I stopped wearing any lingerie during this relationship until 4 years later when I met my now wife.
She loved to dress up and would use any opportunity to do so which I would never complain with. One night she caught me wearing a pair of her lace panties and instead of flying of the handle so to say she calmly asked how long I had been wearing them and why.
Satisfied with my answer she would then day by day tease me more and more during sex about my love of lingerie, often commenting on how much harder my cock would be as she teased me about wearing her panties and hold-up stockings.
One night before bed she produced a pair of open toe black high heel shoes, a pair of black lace boyshorts and a pair of black hold-up stockings complete with red bow and red seam. I commented on how sexy she was going to look in them before she informed me I would be wearing them for the night.
Slightly embarrassed and without much arguement I shyly slipped into the clothes she handed me and quickly hid in bed where she joined me. Running her hands up my legs making me release a noise I couldn't describe from my lips.
Feeling happy with herself she moved her hand to my now painfully erect cock feeling my precum through the fabric and teased me about how turned on I was dressed like a slut.
Needless to say that night I fucked her longer and hard than I was ever able to before and never remembered falling asleep instead waking up the next morning still in my panties stockings and heels. Feeling embarrassed I quickly undressed and avoided the situation for a while.
One night she text me to let me know she would not be coming home due to her being severely drunk. I took the opportunity to dress back in the black slutty clothes she had made me wear and laid in bed running my hands over my lingerie and feeling extremely sexy.
Not wanting to ruin the outfit I slipped my feet into my black sexy heels and tried my best to navigate our small flat. This only turned me on more as I felt the cool air against my stocking clad legs and loving the feeling of my panties against my skin.
Feeling brave I started to rummage through my partner's drawers in search of more panties only to find the dildo I had purchased for her. Suddenly I was caught by a wave of thoughts and found myself staring at this flesh coloured "monster".
Up till this point I had never had one single thought of ever penetrating myself or being penetrated by anything, but standing there in my lingerie and heels holding her dildo I found myself wanting to feel what a woman felt whilst they moan in exctasy.
Finding the lube I used to fulfill her anal fantasy's previously I applied a generous amount to her 8" dildo with was generously girthy and began rubbing my asshole with it, enjoying the feeling of this cock at my asshole I pushed gently and remember the pain as the head slipped inside me catching me off guard and causing me to clamp down on it.
Once I had calmed down I began to enjoy the feeling of this thing inside me despite feeling shame at the idea of being dressed in lingerie taking a dildo to the ass, needless to say I was soon struggling to fit her dildo inside me and was relieved once I had managed to lower myself down it's entire length.
I came harder than I very had and could feel myself clamping down on the thick long dildo in my ass, feeling empty as I pulled it from my ass and proceeded to clean it not wanting my partner to find out.
Unfortunately I did not have the smart idea to remove the items of lingerie I had been wearing and was caught in the morning by my partner. With a little encouragement she convinced me that it was just a link of mine and was happy to let me wear any of her lingerie whenever I wanted , which was handy due to us both being on the shorter side and both being roughly a size 14 I jumped at the opportunity.
Regularly wearing stockings panties and heels around the apartment I began to feel more and more feminine and as sexy as I viewed the models who drew me to the life of wearing lingerie till one night my partner introduced the idea of pegging me.
Upon hearing this it was very hard to hide the raging hard on that had been growing under my lace boyshorts of which she noticed, at this point she knew the idea turned me on and had already begun sifting through her draws producing the dildo I had previously met and had continued to play with any chance I was alone.
She had me lay on my stomach and placed a pillow under my pelvis to raise my ass slightly making it stick out slightly she commented on how good my ass locked in her panties before telling me to remove them so she could slip a thong on me. Feeling my ass cheeks spread slightly she placed the thing string against my ass as she began reading my stocking clad legs running her hands to my heels back up my thighs to my ass cheeks.
I could feel my asshole opening slightly as she press my ass cheeks and tried to hide me excitement as much as possible. I heard her grab the bottle of lube and felt her hand remove the thong string from covering my asshole leaving me exposed as she poured lube all over my ass and asshole rubbing and grabbing my ass, she spread some of the lube into my asshole and set to work lubing up my secret friend.
A moan escaped my lips as she gently pushed the dildo against my asshole which by now was very accustomed to her 8inch dildo, groaning as with little effort she was able to push her dildo deep inside me.
She commented on how horny I must have been as I took her large dildo so easily something she was not easily able to do in her ass. Which then embarrassingly I confessed of my solo play sessions giving great detail as to how I would sit on her dildo pushing down as hard as I could to feel it push deep inside me.
To my suprise she was not angry but instead told me that watching me take her dildo was the sexiest thing she had ever witnessed and made me feel the wet spot she had left under her pussy. Shamefully I asked her to continue and felt her withdraw the entire dildo from my ass before ramming it deep inside me again smiling wickedly as she made me moan.
She took full control of the situation and had her dildo ramming repeatedly deep inside me making me take it like I had given her so many times till I begged her to allow me to fuck her and release the frustration I had built up.
She made me remain wearing my lingerie and heels and began questioning me as to whether or not I was gay to which I replied no I just enjoyed the feeling of anal stimulation.
Feeling she accepted my explanation i attempted to remove my lingerie to which she told me sternly no as she enjoyed me wearing feminine lingerie, this led to me wearing some form of lingerie nightly to bed and around the apartment so she could comment on how good my ass and legs looked. The comments had no started to become more regular and she ..(continue confession)
- That's Juicy! 38
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