u/throwaway78181

not gonna go into details since it's a LONG read (15k+ characters), but my stepdad and I (he raised me since I was 6, never knew my dad) have always been very close. I've been crossdressing a little and he's the only one who knows, I never even told my mom, not because I'm afraid she'll freak out but because I like that this is something I got to keep a secret, I feel like it's bonding us together and it feels very wholesome.

recently some stuff happened between him and I, to make it short he got the habit off giving me his shirt to smell him after gym every friday, (I know what it sounds like but trust me it's not creepy, let me know if you want the full story) and last week he didn't only give me his shirt, he game me his underwear, and OKAY this is like... very different.

the thing is friday is today, and I'm not sure if I should plan something or act on it or just wait to see what he does, because clearly my entire body is screaming YES PLEASE but my mind is so fucked, I don't want to do this to my mom and I know there is no going back.

oh and also he knows I wear female underwear, saw me wearing them and I sneaked on him smelling them and masturbating to it, so clearly he wants something to happen.

also I would talk about the whole thing but all I got from discord was homophobic insults and death threats, so now I give the full story to people who actively want it, I'm here for advice, not "kys" in my dms...

my whole account is a throwaway so not gonna stay forever but if you have questions, shoot

my dad left my mom when she was pregnant, I never met him (and probably won't ever), she raised me by herself until she presented me to her new boyfriend, with all the available patience she wanted to make sure I was okay with all of it. I was 6, she was 29 and he was 40.

she was pretty scared but I was pretty unaware of what it meant, as a kid I was pretty much respecting any of my mom's decision.

later I learned that it was going on for almost a year before I heard about him, when they decided he would move in, he always wanted a son, he wasn't getting any younger and he really was in love with my mom.

I'm saying was but they are still together, more on that later.

fast-forward 7 years later, I'm discovering myself, my body and my sexuality. the more I grow up, the more I can tell I'm more in-love with how the girls dress rather than them.

it's when I had my first kiss with one of my best-friend's older brother than everything snapped, I could feel the butterflies in my tummy, the electricity in the back of my head, it was a brief kiss but omg. when we talked about it he told me I would look beautiful in her sister's clothing.

he was only 2 years older than me, and we never did anything else than kiss here and there when people weren't looking.

week after week he stole clothes from his sister and brang them to school to give them to me, I would go home, try them on with my heart pouding out of my chest and send him pictures.

thinking back I think he was more into me being a girl rather than me being gay, he never really tried to touch me or to make me touch him, he just loved kissing me and pretending I was a girl.

one night as I was using mom's make-up as usual to dress-up, I heard a noise behind me. my stepdad was there, I thought he was out but he was only napping.

I froze and so did he, we shared a look in the mirror for what seemed an eternity, I was honestly almost naked, wearing bra filled with socks and panties, my hair tied, lipstick and mascara on.

He said "Sorry" and left the room, I was in panic mode, I started shaking like crazy.

I undressed in haste and took my make up off in haste. I put on some pants and a shirt before getting out of my room and looking for him. I knocked on his bedroom door and opened in silence.

I asked if he was going to tell my mom, he said he won't but I should tell her. I asked if he was mad and he said he wasn't, just surprised. the conversation continued where he tried to convince me to tell my mom and I was crying telling him I couldn't do it, seeing my distress he told me it was okay and that I could always open up to him if needed and I would tell my mom whenever I felt ready.

after that moment, he and I became weirdly closer than ever, we were already getting along, but sharing this actually made me want to spend more time with him, I started snuggling with him in the sofa while we were all watching TV, I started hugging him more, and as the school year was coming to an end and my sister's brother was changing school (and he became more distant), I felt more and more alone if it wasn't for the time I spent with him, after all he was the second person to know.

during the summer, he and I were out for groceries, we went past the clothing section. he stopped at a shirt, white with a pink heart on it with glimmer. he looked at it and asked if I liked it, I asked "For mom ?" and he said "No, for you." I blushed so hard, and looked around to see if anyone was near. he and I didn't talk about it at all but we were close enough and I guess we shared that secret.

I said "I'm good don't worry." but he put it in the cart anyway, I couldn't believe he was actually doing it, I thought he was making a joke but he wasn't, we went to checkout, I was bright red, the cashier girl probably thought I was weird, I mean he wasn't buying a sextoy or anything, but yeah. as we got to the car he gave me the shirt and told me to hide it when we got home.

during this night I couldn't sleep, I don't know why but the way he acted gave him so much authority over me I genuinely got hot, I was looking at him in the same way I was looking at porn. I barely slept in my own sweat and pants that night.

the next day, a saturday, as my mom was at work, he offered we spend the day watching TV, I said yes and as a surprise I wore the t-shirt he gave me with panties and light pajama pants. he smiled and told me I was very cute in it, as we watched TV under the blanket. at some point, trembling, I took off my pants from under the blanket and tossed them to the side of the sofa, then put my hairless legs on his. he put his big arm over my shoulder and pulled my against him.

I was burning, my erection was piercing through the panties and clearly he could feel it, both the erection and the lacework, but he didn't react, he just let me pant in his arms, all fragile.

at some point I stopped shaking, I was just in bliss.

at some point I found the courage and offered a drink, I got out of the blanket and walked to the kitchen, my bare ass visible, grabbed a drink and came back.

he smile and grabbed it, he got completely rid of the blanket and sat next to him.

I thought something would happen but his phone rang, my mom was downstairs and asked if he started cooking dinner.

I jumped out of the sofa, and wore my pajama back with another top.

the evening went alright, my mom was tired so she asked if she could go to the shower and go to bed before my dad, he said yes and that he would do the dishes.

after we were done eating, my mom went to bed and I went to the shower, after 10 minutes of scrolling on my phone I realized I was still not showering but I actually forgot my towel in my room. so I went back, still on my phone, and as I approached the door, in the same mirror my stepdad saw me doing my make up, I saw him sitting on my bed, my panties to his nose, his underwear to his ankles, he was masturbating furiously to my smell, I could hear him pant and breathe, licking the interior or my panties.

alright I would tell you guys more but I have to go, let me know if you want the rest.

my whole account is a throwaway so not gonna stay forever but if you have questions, shoot

my dad left my mom when she was pregnant, I never met him (and probably won't ever), she raised me by herself until she presented me to her new boyfriend, with all the available patience she wanted to make sure I was okay with all of it. I was 6, she was 29 and he was 40.

she was pretty scared but I was pretty unaware of what it meant, as a kid I was pretty much respecting any of my mom's decision.

later I learned that it was going on for almost a year before I heard about him, when they decided he would move in, he always wanted a son, he wasn't getting any younger and he really was in love with my mom.

I'm saying was but they are still together, more on that later.

fast-forward 7 years later, I'm discovering myself, my body and my sexuality. the more I grow up, the more I can tell I'm more in-love with how the girls dress rather than them.

it's when I had my first kiss with one of my best-friend's older brother than everything snapped, I could feel the butterflies in my tummy, the electricity in the back of my head, it was a brief kiss but omg. when we talked about it he told me I would look beautiful in her sister's clothing.

he was only 2 years older than me, and we never did anything else than kiss here and there when people weren't looking.

week after week he stole clothes from his sister and brang them to school to give them to me, I would go home, try them on with my heart pouding out of my chest and send him pictures.

thinking back I think he was more into me being a girl rather than me being gay, he never really tried to touch me or to make me touch him, he just loved kissing me and pretending I was a girl.

one night as I was using mom's make-up as usual to dress-up, I heard a noise behind me. my stepdad was there, I thought he was out but he was only napping.

I froze and so did he, we shared a look in the mirror for what seemed an eternity, I was honestly almost naked, wearing bra filled with socks and panties, my hair tied, lipstick and mascara on.

He said "Sorry" and left the room, I was in panic mode, I started shaking like crazy.

I undressed in haste and took my make up off in haste. I put on some pants and a shirt before getting out of my room and looking for him. I knocked on his bedroom door and opened in silence.

I asked if he was going to tell my mom, he said he won't but I should tell her. I asked if he was mad and he said he wasn't, just surprised. the conversation continued where he tried to convince me to tell my mom and I was crying telling him I couldn't do it, seeing my distress he told me it was okay and that I could always open up to him if needed and I would tell my mom whenever I felt ready.

after that moment, he and I became weirdly closer than ever, we were already getting along, but sharing this actually made me want to spend more time with him, I started snuggling with him in the sofa while we were all watching TV, I started hugging him more, and as the school year was coming to an end and my sister's brother was changing school (and he became more distant), I felt more and more alone if it wasn't for the time I spent with him, after all he was the second person to know.

during the summer, he and I were out for groceries, we went past the clothing section. he stopped at a shirt, white with a pink heart on it with glimmer. he looked at it and asked if I liked it, I asked "For mom ?" and he said "No, for you." I blushed so hard, and looked around to see if anyone was near. he and I didn't talk about it at all but we were close enough and I guess we shared that secret.

I said "I'm good don't worry." but he put it in the cart anyway, I couldn't believe he was actually doing it, I thought he was making a joke but he wasn't, we went to checkout, I was bright red, the cashier girl probably thought I was weird, I mean he wasn't buying a sextoy or anything, but yeah. as we got to the car he gave me the shirt and told me to hide it when we got home.

during this night I couldn't sleep, I don't know why but the way he acted gave him so much authority over me I genuinely got hot, I was looking at him in the same way I was looking at porn. I barely slept in my own sweat and pants that night.

the next day, a saturday, as my mom was at work, he offered we spend the day watching TV, I said yes and as a surprise I wore the t-shirt he gave me with panties and light pajama pants. he smiled and told me I was very cute in it, as we watched TV under the blanket. at some point, trembling, I took off my pants from under the blanket and tossed them to the side of the sofa, then put my hairless legs on his. he put his big arm over my shoulder and pulled my against him.

I was burning, my erection was piercing through the panties and clearly he could feel it, both the erection and the lacework, but he didn't react, he just let me pant in his arms, all fragile.

at some point I stopped shaking, I was just in bliss.

at some point I found the courage and offered a drink, I got out of the blanket and walked to the kitchen, my bare ass visible, grabbed a drink and came back.

he smile and grabbed it, he got completely rid of the blanket and sat next to him.

I thought something would happen but his phone rang, my mom was downstairs and asked if he started cooking dinner.

I jumped out of the sofa, and wore my pajama back with another top.

the evening went alright, my mom was tired so she asked if she could go to the shower and go to bed before my dad, he said yes and that he would do the dishes.

after we were done eating, my mom went to bed and I went to the shower, after 10 minutes of scrolling on my phone I realized I was still not showering but I actually forgot my towel in my room. so I went back, still on my phone, and as I approached the door, in the same mirror my stepdad saw me doing my make up, I saw him sitting on my bed, my panties to his nose, his underwear to his ankles, he was masturbating furiously to my smell, I could hear him pant and breathe, licking the interior or my panties.

alright I would tell you guys more but I have to go, let me know if you want the rest.