My Girlfriend s Girlfriend
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My First Girlfriend Vol.3 free porn video
Chapter 9: Friday
Friday morning when searching through my collection, I could not find any pairs that weren't thongs. I could have sworn there were more bikinis and briefs but I guess I was mistaken. And I guess today's the day I wear a thong all day. Up to this point I had been choosing pairs that seemed the least feminine - something I could maaaayyybe pass off as European mens or something - but today something in me had switched. I was tired of trying to pretend to myself that I wasn't in a humiliating situation of being forced into girls underwear. In fact that humiliating situation started to feel like a turn-on. and the sneaking around and secrecy had made things kind of exciting. So I thought 'fuck it' let's have fun with it. I found the pair that I deemed to be the girliest: a black and white polka dot thong with a hot pink lacy waistband. If a girl were wearing this, I'd find it super hot. And the thought being seen wearing it made me feel so degraded and pathetic that it... was.... kind of sexy? I didn't fully understand my thought process, but I felt a fun little rush as I pulled them up my legs. The thrill of doing something bad and hoping no one finds out. I had totally forgotten that I was being forced to do this - it was genuinely fun for me now.
The phrase 'naughty girl' was floating around my head all day. In one of my morning classes, I thought I heard someone say "he's a sissy" and I swear my heart stopped. What they actually said was "he's so busy" and they weren't even talking about me. False alarm. Thank God. The sensation of the thong between my cheeks kept me aware of my predicament, but I had a reached a bizarre state where my arousal had plateaued and I was now used to it. Still shivery and anxious, but I'd come to accept it. As an added bonus, it seemed like my dick wasn't fighting with its cage as much. The arousal I felt was no longer focused in my penis but was spread throughout my entire body, where it was more manageable. I was in a more calm state finally. Until lunch that is, when I realized Catherine was going to see the slutty panties that I had chosen for myself. Ugh there's no way she wasn't going to make fun of me for it. But I made my choice. And at least I get to see hers (and that red thong was pretty damn slutty).
I was walking faster than usual on our way to her house - to the point where she asked if I was in a hurry or something. I said no, just had a lot of energy today. She laughed and said "That's good. I want to try something fun with you today if you're up for it" My mind immediately started racing with possibilities of what that could mean. Was she going to let me out of chastity? play a game of 'naked twister'? Put on a striptease for me? Sit her cute ass on my dick and ride it until I explode inside her? Fuck I shouldn't have been thinking all those thoughts because now my dick was fighting to get erect. And we were definitely not about to play 'naked twister'.
I asked her what she wanted to try. She explained that she'd been thinking about Rebecca and I, and how Rebecca was 'sissifying' me. Catherine thought it might be fun to give me a little makeover. I stopped listening after the word "sissify" because I had never heard that before. I asked my friend what it meant. "Oh, it just means like, when a girl likes her boyfriend to be more girly. So like, making your body smooth and wearing panties and stuff like that. Lots of people are into it these days." So this was something that other people were doing too. I wasn't just some weirdo with a weirdo girlfriend. We were doing a common thing called 'sissification'. I wanted to know more.
"What does it mean? Like, why does she want me to be girly? I thought girls liked manly men?" I inquired of my friend.
"I dunno. You'd have to ask Rebecca about that. Different people like different things. For what its worth, I think you'll make a very cute girl. Honestly I'm jealous of how good you look in your underwear. Most girls would die to be that thin." I insisted that Catherine looked amazing in her underwear, and she just laughed. I couldn't believe this curvy little angel didn't realize what an image of beauty she was. We were already in her bedroom by the time I realized I had agreed to a makeover. What did that even mean for a boy? Wait, was she going to dress me up as a girl?
"Okay" she chimed in "We can use my makeup, and I have a wig from halloween haha. We can borrow one of my sister's training bras, aaaaand probably one of her skirts too. I think my shirts will fit those narrow shoulders of yours." She scurried around her room gathering items while I sat on the bed. My heart was racing a bit. This was a big step up from wearing panties under my boy clothes. And even though I trusted my friend and felt comfortable with her, the thought of being dressed as a girl in front of someone else felt... wrong. But also exciting. I was pretty sure I would look silly, but deep down I felt part of me desiring to look hot. "Actually you know what? Let's see what underwear you've got on, and I'll put together an outfit to match your style! Yeah go ahead and take your boy clothes off."
She sat on her bed and waited for me to act. I was frozen. Why had I chosen to wear the sluttiest panties today? For the thrill of humiliation? Well I guess I was about to get my wish...
"Oh wait" she interrupted "I almost forgot our deal." She laid back on her bed and slid her jeans right off, revealing her black 'cheeky' panties with white trim. I tried not to stare as I undid my jeans and shimmied out of them, revealing my lacy polka dot, pink, black, and white thong. I braced myself for ridicule. Catherine just stared at my midsection for a moment. I wondered what was going through her head. Then she burst out laughing "Hahaha what are those!? They're so slutty! Rebecca bought you those!? Oh my god haha." She got up and walked around me, taking a full evaluation. I was paralyzed by my embarrassment.
"SO I guess you really are into this sissy-boy stuff eh? Well alright. If you wanna look like a slut, I'll help you." She went and dug out some white thigh-high socks with pink stripes at the top and told me to put them on. I sat and worked them up my legs, while also feasting my eyes on her ass every time her back was turned. God I wanted to fuck her, but instead I was letting her dress me up like a slut? what was happening to me? Then again this actually felt much easier and more natural to me than initiating sex with an attractive girl (something I'd still never done, technically). It was so sexy and intimate, but without me feeling like I'm imposing on a girl. Trying to fuck someone always felt like I was imposing on them, and I want to be a nice person. Something deep in my heart was telling me 'if you can't get your dick inside of her, you must become like her in order to satisfy your thirst for the feminine'. I could now intuit that my male sex drive was really just a thirst for the feminine - and I was satisfying that thirst in a different way. Dressing up as a girl was starting to seem more appealing to me than sex.
My gorgeous companion brought me a training bra and a tight black long-sleeve, both of which I eagerly put on. All my pent up desire to fuck a girl had now been redirected into a desire to become as much of a girl as possible. Last she brought me a short pink skit, which she helped me step into. She stood back and admired her work, saying that from the neck down I look like her friend Brooke. We both laughed hard at that, because Brooke had a bit of a 'reputation'. Next, she sat me down at her desk and pulled out her makeup. She lifted my chin and told me to hold still. I just closed my eyes and let her work. I had no knowledge of makeup at this point. I assume she used some foundation or concealer or whatever to set a base. I could feel her doing stuff to my eyelids and eyelashes. All these delicate little sensations on my face I'd never felt before - they were forbidden to boys. But thankfully the two girls closest to me had taken pity on my soul and dragged me into their world of beauty, style, comfort, and luxury. Lastly, she had me open my mouth while she applied some pink bubblegum lip gloss. having her gently paint my soft lips was one of the most sensual moments of my life.
Once my makeup was done, she placed the long black wig on my head and did some rearranging to get it to look natural. "All done!" she declared as she stood back to look at her handiwork. "Oh my god... You really do look like one of the trashy girls at our school haha! I can't believe how well this turned out. Look!"
She directed me to a mirror, but it took me a few seconds to realize that the sultry babe I was gazing upon was actually myself. I was in shock. At first I thought I was dreaming, then as I moved around and inhabited my new look, a wave of glee started to wash over me. I felt that full-body arousal I had experienced the other day. I not only looked entirely like a girl, but Catherine was right - I was actually pretty cute. As a boy, I had never liked how I looked. Never felt good about my appearance. Suddenly I could actually imagine people finding me attractive. I was painfully curious if that would turn out to be true. "Catherine, do you think like... guys could possibly find me hot?" I was filled with wonder and uncertainty, but Catherine seemed fully confident.
"Dude, I am positive if we sent pics of you to some guys without showing your face, they would be all over it... Oh my god we should actually do that. Think of how funny that would be. Especially if we got some of those homophobic jerks on the football team haha." I felt hesitant because I still wasn't comfortable having anyone besides Catherine and Rebecca see me as a sissy, but I couldn't resist my desire for validation of my hotness. And we wouldn't show my face anyway... Okay Catherine, game on.
Chapter 10: Vanity
We decided to cut our afternoon classes and have some fun with my new look. My partner in crime put on some music, pulled out her camera, and started directing me. The camera did make me nervous, but I know Catherine wouldn't ruin my life. She told me to turn around and try to stick my butt out. I did the best I could. She said it was perfect and tried a few different angles. She then paused and hummed and hawed for a moment.
"Hmm it needs more. I think we should lift up your skirt and show some of your ass. That'll definitely give them boners haha" Frankly, I was a little shocked that my sweet modest friend Catherine was acting this... naughty. Her energy rubbed off on me and I felt a bit naughty too. After all I looked like a hot girl and I was starting to feel the part. Also, the thought of my ass in a thong causing some big dumb jock guy to have a boner brought up some strange feelings; power? But not physical power of course, more like psychological power - the ability to manipulate and entice. But it came with a sense of vulnerability as well - like being a target or a prey. Like what if a big strong guy figured out it was me and wanted to actually fuck me? I wouldn't be strong enough to fight him off. He'd be able to do whatever he wants to me. Oh my god is this how pretty girls feel all the time? I simultaneously sympathized with Rebecca while also being envious of the power she wields.
While I pondered my new perspective on gender relations, I had been holding up my skirt to reveal some of my ass - not all. Catherine seemed to be getting some good shots because she kept giggling to herself. "Okay you wanna see?" she showed me her phone and scrolled through a couple of her favorite shots. I was floored. I had a smooth round little bubble butt, and the pink skirt and white thigh high socks framed it as being unmistakably female. The illusion was totally convincing.
"Who should I send it to? OH I know! Lawson! yeah, and Brandon and Dave too. Oh and Christian haha." Those were 4 of the buffest dudes in our class. They had all said disparaging or homophobic things to me or about me at some point. Something about getting them horny for my girly ass felt like a twisted form of payback. We sent out a couple butt pics to each guy with the message "My friend wants to know if you think she's hot ;)". We both giggled hysterically. While we waited for their replies we lounged and watched TV. Some daytime trash about people cheating on each other. I felt bad for this one guy; he was a weak nerdy type kind of like me, and he'd been dating this beautiful woman for like 3 years. Then he found out the whole time that she'd been fucking her personal trainer. I think the worst part was that when confronted, she told him 'I do love you baby, you're just not enough for me sexually. I need more. I want you to stay with me, but I also need something else'. Can you imagine? Having the woman you love tell you you're sexually inadequate, but expecting you to stay loyal to her? it boggled my mind. I felt deeply relieved that Rebecca was attracted to me even though I'm feminine for a boy. I really lucked out I guess.
After an hour or so, replies started rolling in, and we were giddy with excitement. The first one was from Dave "fuck yeah she looks good!" We laughed hard that he actually referred to me as 'she'. it was a little thing but it struck a nerve. Christian and Brandon both said I had a hot ass, but wanted to know more, see my face, etc. So it didn't go any further. We still got a kick out of it though. And then Lawson said "Sure I'd fuck that ass as long as her face isn't bad. ask her if she wants to hook up"
We laughed hysterically at that one, because Lawson is a very straight-laced preppy type but I'd always heard rumors that he was secretly a dog. It was just funny to see his thirstiness directed at the k** he always made fun of for being a loser. Something about the dynamic was very erotic to me; as a boy I was a 'loser' but slap some clothes and makeup on me and now this alpha male wants to fuck me? It made me feel like the masculinity I had been clutching was actually just holding me back. I felt like I had fallen so low through the male ranks that I passed through the margin and came out the other side as a desirable sexual object. Maybe this was how I should have been living all along? My whole life I'd been implanted with the idea that the worst thing a boy can be is 'girly' but now I was wondering if some boys aren't meant to be boys. Maybe the bullying and ridicule from other males, and the benevolence and guidance of females is part of some natural order to recycle inadequate males into sexually valuable fems.
These were all thoughts that I would have mull over when I go to bed. For now I was still hanging out and laughing with my friend Catherine. "I would call this a great success" she quipped. "Can I please take a pic showing your face? I'm just so proud of what a good job I did haha. I promise not to show anyone unless you want me to. Honestly I don't even think anyone would recognize you from this. You look like a totally different person." I couldn't say no to this wonderful girl. I agreed to let her do a little photoshoot just for herself. She began directing me like a photographer would to a model. She had me pose different ways and give different looks as she bounced around me trying different angles. I was really enjoying watching her frolicking in her underwear, and because I felt like a girl at this point, I didn't feel guilty about it. I felt like 'yeah, the feminine is my home right now. I am welcome here. I am not imposing'. It was such a relief to be able to interact with a girl and not feel afraid of offending her with my very presence.
After Catherine got her fill of pics, we sat and looked at our little gallery. She really had done an amazing job - I didn't look like my boy self at all. She asked me curiously what I thought Rebecca would think of this. I honestly wasn't sure. I hadn't even heard from my girlfriend in almost a week now. Catherine suggested we send her a pic. "Don't be shy. I know she'll think its adorable. Besides, she's already seen you naked. Seeing you in girls clothes is like, less scandalous than that." I was dubious of her logic there, but I did want to know what Rebecca thought. Would she think its cute? Would it turn her on? Would she laugh? I had to know, so I gave Catherine the green light to send a pic of me that shows my full outfit and face.
The message said 'Look how hot your boyfriend is now!'. We giggled together as she hit send. I knew Rebecca was busy this week so we didn't sit around and wait for a response. It was getting close to the time when I would have been leaving school anyway, and Catherine had to study. "Can I do one more quick thing before you change back?" she asked, almost sounding like this was some magic spell that would soon be undone. "Anything" I said (and meant it). She told me to sit on the edge of the bed and close my eyes. I obliged, wondering what was coming next. She stood in front of me and lifted my chin up like when she was doing my make up, but instead of a makeup brush or lip gloss applicator, I felt her nose graze mine, smelled her sweet perfume, and finally felt her soft lips press against mine for a few seconds. I was enveloped in her gentle aura. I had butterflies in my stomach. My little caged penis twitched in its shell, and I felt just a few drops of wetness escape into my panties. It was the closest thing to a release I'd had all week, and it felt like the consummation of all the unbearable sexual tension that had been building. She slowly broke the kiss but kept her face a few inches from mine. "I always wanted to try kissing a girl. Don't tell anyone okay?" I promised her it would be our little secret. I changed back into my boy clothes (with the exception of my panties), and we hugged before I headed home.
Later that night after dinner, Rebecca texted me:
"BABY I miss you. Catherine showed me the pic. you make such a gorgeous girl. you're like, hotter than me. its actually kind of fucked up haha"
I replied saying no one is hotter than her, but that I had a lot of fun dressing up with my friend. I even told her about what we did to the jocks. she replied:
"WHAAAAAT NO YOU DID NOT! LOL are you serious?"
I told her I was indeed serious, and said something about how dumb and thirsty those guys are.
"omfg baby thats fucking hilarious. those guys WISH they could fuck my boyfriend lmao. hmm maybe I'll pimp you out and make a bit of cash on the side haha. what do you say slut? wanna be my hooker boyfriend?"
I laughed and said I didn't think they'd want to fuck me anymore once they knew I was a boy.
"honestly when you look like that, I don't think they'd mind haha"
We went on chatting and catching up on how our weeks went. Then she told me that her parents were away all day tomorrow and Sunday, and that I should come stay with her for two whole days. I was thrilled of course.
Friday morning when searching through my collection, I could not find any pairs that weren't thongs. I could have sworn there were more bikinis and briefs but I guess I was mistaken. And I guess today's the day I wear a thong all day. Up to this point I had been choosing pairs that seemed the least feminine - something I could maaaayyybe pass off as European mens or something - but today something in me had switched. I was tired of trying to pretend to myself that I wasn't in a humiliating situation of being forced into girls underwear. In fact that humiliating situation started to feel like a turn-on. and the sneaking around and secrecy had made things kind of exciting. So I thought 'fuck it' let's have fun with it. I found the pair that I deemed to be the girliest: a black and white polka dot thong with a hot pink lacy waistband. If a girl were wearing this, I'd find it super hot. And the thought being seen wearing it made me feel so degraded and pathetic that it... was.... kind of sexy? I didn't fully understand my thought process, but I felt a fun little rush as I pulled them up my legs. The thrill of doing something bad and hoping no one finds out. I had totally forgotten that I was being forced to do this - it was genuinely fun for me now.
The phrase 'naughty girl' was floating around my head all day. In one of my morning classes, I thought I heard someone say "he's a sissy" and I swear my heart stopped. What they actually said was "he's so busy" and they weren't even talking about me. False alarm. Thank God. The sensation of the thong between my cheeks kept me aware of my predicament, but I had a reached a bizarre state where my arousal had plateaued and I was now used to it. Still shivery and anxious, but I'd come to accept it. As an added bonus, it seemed like my dick wasn't fighting with its cage as much. The arousal I felt was no longer focused in my penis but was spread throughout my entire body, where it was more manageable. I was in a more calm state finally. Until lunch that is, when I realized Catherine was going to see the slutty panties that I had chosen for myself. Ugh there's no way she wasn't going to make fun of me for it. But I made my choice. And at least I get to see hers (and that red thong was pretty damn slutty).
I was walking faster than usual on our way to her house - to the point where she asked if I was in a hurry or something. I said no, just had a lot of energy today. She laughed and said "That's good. I want to try something fun with you today if you're up for it" My mind immediately started racing with possibilities of what that could mean. Was she going to let me out of chastity? play a game of 'naked twister'? Put on a striptease for me? Sit her cute ass on my dick and ride it until I explode inside her? Fuck I shouldn't have been thinking all those thoughts because now my dick was fighting to get erect. And we were definitely not about to play 'naked twister'.
I asked her what she wanted to try. She explained that she'd been thinking about Rebecca and I, and how Rebecca was 'sissifying' me. Catherine thought it might be fun to give me a little makeover. I stopped listening after the word "sissify" because I had never heard that before. I asked my friend what it meant. "Oh, it just means like, when a girl likes her boyfriend to be more girly. So like, making your body smooth and wearing panties and stuff like that. Lots of people are into it these days." So this was something that other people were doing too. I wasn't just some weirdo with a weirdo girlfriend. We were doing a common thing called 'sissification'. I wanted to know more.
"What does it mean? Like, why does she want me to be girly? I thought girls liked manly men?" I inquired of my friend.
"I dunno. You'd have to ask Rebecca about that. Different people like different things. For what its worth, I think you'll make a very cute girl. Honestly I'm jealous of how good you look in your underwear. Most girls would die to be that thin." I insisted that Catherine looked amazing in her underwear, and she just laughed. I couldn't believe this curvy little angel didn't realize what an image of beauty she was. We were already in her bedroom by the time I realized I had agreed to a makeover. What did that even mean for a boy? Wait, was she going to dress me up as a girl?
"Okay" she chimed in "We can use my makeup, and I have a wig from halloween haha. We can borrow one of my sister's training bras, aaaaand probably one of her skirts too. I think my shirts will fit those narrow shoulders of yours." She scurried around her room gathering items while I sat on the bed. My heart was racing a bit. This was a big step up from wearing panties under my boy clothes. And even though I trusted my friend and felt comfortable with her, the thought of being dressed as a girl in front of someone else felt... wrong. But also exciting. I was pretty sure I would look silly, but deep down I felt part of me desiring to look hot. "Actually you know what? Let's see what underwear you've got on, and I'll put together an outfit to match your style! Yeah go ahead and take your boy clothes off."
She sat on her bed and waited for me to act. I was frozen. Why had I chosen to wear the sluttiest panties today? For the thrill of humiliation? Well I guess I was about to get my wish...
"Oh wait" she interrupted "I almost forgot our deal." She laid back on her bed and slid her jeans right off, revealing her black 'cheeky' panties with white trim. I tried not to stare as I undid my jeans and shimmied out of them, revealing my lacy polka dot, pink, black, and white thong. I braced myself for ridicule. Catherine just stared at my midsection for a moment. I wondered what was going through her head. Then she burst out laughing "Hahaha what are those!? They're so slutty! Rebecca bought you those!? Oh my god haha." She got up and walked around me, taking a full evaluation. I was paralyzed by my embarrassment.
"SO I guess you really are into this sissy-boy stuff eh? Well alright. If you wanna look like a slut, I'll help you." She went and dug out some white thigh-high socks with pink stripes at the top and told me to put them on. I sat and worked them up my legs, while also feasting my eyes on her ass every time her back was turned. God I wanted to fuck her, but instead I was letting her dress me up like a slut? what was happening to me? Then again this actually felt much easier and more natural to me than initiating sex with an attractive girl (something I'd still never done, technically). It was so sexy and intimate, but without me feeling like I'm imposing on a girl. Trying to fuck someone always felt like I was imposing on them, and I want to be a nice person. Something deep in my heart was telling me 'if you can't get your dick inside of her, you must become like her in order to satisfy your thirst for the feminine'. I could now intuit that my male sex drive was really just a thirst for the feminine - and I was satisfying that thirst in a different way. Dressing up as a girl was starting to seem more appealing to me than sex.
My gorgeous companion brought me a training bra and a tight black long-sleeve, both of which I eagerly put on. All my pent up desire to fuck a girl had now been redirected into a desire to become as much of a girl as possible. Last she brought me a short pink skit, which she helped me step into. She stood back and admired her work, saying that from the neck down I look like her friend Brooke. We both laughed hard at that, because Brooke had a bit of a 'reputation'. Next, she sat me down at her desk and pulled out her makeup. She lifted my chin and told me to hold still. I just closed my eyes and let her work. I had no knowledge of makeup at this point. I assume she used some foundation or concealer or whatever to set a base. I could feel her doing stuff to my eyelids and eyelashes. All these delicate little sensations on my face I'd never felt before - they were forbidden to boys. But thankfully the two girls closest to me had taken pity on my soul and dragged me into their world of beauty, style, comfort, and luxury. Lastly, she had me open my mouth while she applied some pink bubblegum lip gloss. having her gently paint my soft lips was one of the most sensual moments of my life.
Once my makeup was done, she placed the long black wig on my head and did some rearranging to get it to look natural. "All done!" she declared as she stood back to look at her handiwork. "Oh my god... You really do look like one of the trashy girls at our school haha! I can't believe how well this turned out. Look!"
She directed me to a mirror, but it took me a few seconds to realize that the sultry babe I was gazing upon was actually myself. I was in shock. At first I thought I was dreaming, then as I moved around and inhabited my new look, a wave of glee started to wash over me. I felt that full-body arousal I had experienced the other day. I not only looked entirely like a girl, but Catherine was right - I was actually pretty cute. As a boy, I had never liked how I looked. Never felt good about my appearance. Suddenly I could actually imagine people finding me attractive. I was painfully curious if that would turn out to be true. "Catherine, do you think like... guys could possibly find me hot?" I was filled with wonder and uncertainty, but Catherine seemed fully confident.
"Dude, I am positive if we sent pics of you to some guys without showing your face, they would be all over it... Oh my god we should actually do that. Think of how funny that would be. Especially if we got some of those homophobic jerks on the football team haha." I felt hesitant because I still wasn't comfortable having anyone besides Catherine and Rebecca see me as a sissy, but I couldn't resist my desire for validation of my hotness. And we wouldn't show my face anyway... Okay Catherine, game on.
Chapter 10: Vanity
We decided to cut our afternoon classes and have some fun with my new look. My partner in crime put on some music, pulled out her camera, and started directing me. The camera did make me nervous, but I know Catherine wouldn't ruin my life. She told me to turn around and try to stick my butt out. I did the best I could. She said it was perfect and tried a few different angles. She then paused and hummed and hawed for a moment.
"Hmm it needs more. I think we should lift up your skirt and show some of your ass. That'll definitely give them boners haha" Frankly, I was a little shocked that my sweet modest friend Catherine was acting this... naughty. Her energy rubbed off on me and I felt a bit naughty too. After all I looked like a hot girl and I was starting to feel the part. Also, the thought of my ass in a thong causing some big dumb jock guy to have a boner brought up some strange feelings; power? But not physical power of course, more like psychological power - the ability to manipulate and entice. But it came with a sense of vulnerability as well - like being a target or a prey. Like what if a big strong guy figured out it was me and wanted to actually fuck me? I wouldn't be strong enough to fight him off. He'd be able to do whatever he wants to me. Oh my god is this how pretty girls feel all the time? I simultaneously sympathized with Rebecca while also being envious of the power she wields.
While I pondered my new perspective on gender relations, I had been holding up my skirt to reveal some of my ass - not all. Catherine seemed to be getting some good shots because she kept giggling to herself. "Okay you wanna see?" she showed me her phone and scrolled through a couple of her favorite shots. I was floored. I had a smooth round little bubble butt, and the pink skirt and white thigh high socks framed it as being unmistakably female. The illusion was totally convincing.
"Who should I send it to? OH I know! Lawson! yeah, and Brandon and Dave too. Oh and Christian haha." Those were 4 of the buffest dudes in our class. They had all said disparaging or homophobic things to me or about me at some point. Something about getting them horny for my girly ass felt like a twisted form of payback. We sent out a couple butt pics to each guy with the message "My friend wants to know if you think she's hot ;)". We both giggled hysterically. While we waited for their replies we lounged and watched TV. Some daytime trash about people cheating on each other. I felt bad for this one guy; he was a weak nerdy type kind of like me, and he'd been dating this beautiful woman for like 3 years. Then he found out the whole time that she'd been fucking her personal trainer. I think the worst part was that when confronted, she told him 'I do love you baby, you're just not enough for me sexually. I need more. I want you to stay with me, but I also need something else'. Can you imagine? Having the woman you love tell you you're sexually inadequate, but expecting you to stay loyal to her? it boggled my mind. I felt deeply relieved that Rebecca was attracted to me even though I'm feminine for a boy. I really lucked out I guess.
After an hour or so, replies started rolling in, and we were giddy with excitement. The first one was from Dave "fuck yeah she looks good!" We laughed hard that he actually referred to me as 'she'. it was a little thing but it struck a nerve. Christian and Brandon both said I had a hot ass, but wanted to know more, see my face, etc. So it didn't go any further. We still got a kick out of it though. And then Lawson said "Sure I'd fuck that ass as long as her face isn't bad. ask her if she wants to hook up"
We laughed hysterically at that one, because Lawson is a very straight-laced preppy type but I'd always heard rumors that he was secretly a dog. It was just funny to see his thirstiness directed at the k** he always made fun of for being a loser. Something about the dynamic was very erotic to me; as a boy I was a 'loser' but slap some clothes and makeup on me and now this alpha male wants to fuck me? It made me feel like the masculinity I had been clutching was actually just holding me back. I felt like I had fallen so low through the male ranks that I passed through the margin and came out the other side as a desirable sexual object. Maybe this was how I should have been living all along? My whole life I'd been implanted with the idea that the worst thing a boy can be is 'girly' but now I was wondering if some boys aren't meant to be boys. Maybe the bullying and ridicule from other males, and the benevolence and guidance of females is part of some natural order to recycle inadequate males into sexually valuable fems.
These were all thoughts that I would have mull over when I go to bed. For now I was still hanging out and laughing with my friend Catherine. "I would call this a great success" she quipped. "Can I please take a pic showing your face? I'm just so proud of what a good job I did haha. I promise not to show anyone unless you want me to. Honestly I don't even think anyone would recognize you from this. You look like a totally different person." I couldn't say no to this wonderful girl. I agreed to let her do a little photoshoot just for herself. She began directing me like a photographer would to a model. She had me pose different ways and give different looks as she bounced around me trying different angles. I was really enjoying watching her frolicking in her underwear, and because I felt like a girl at this point, I didn't feel guilty about it. I felt like 'yeah, the feminine is my home right now. I am welcome here. I am not imposing'. It was such a relief to be able to interact with a girl and not feel afraid of offending her with my very presence.
After Catherine got her fill of pics, we sat and looked at our little gallery. She really had done an amazing job - I didn't look like my boy self at all. She asked me curiously what I thought Rebecca would think of this. I honestly wasn't sure. I hadn't even heard from my girlfriend in almost a week now. Catherine suggested we send her a pic. "Don't be shy. I know she'll think its adorable. Besides, she's already seen you naked. Seeing you in girls clothes is like, less scandalous than that." I was dubious of her logic there, but I did want to know what Rebecca thought. Would she think its cute? Would it turn her on? Would she laugh? I had to know, so I gave Catherine the green light to send a pic of me that shows my full outfit and face.
The message said 'Look how hot your boyfriend is now!'. We giggled together as she hit send. I knew Rebecca was busy this week so we didn't sit around and wait for a response. It was getting close to the time when I would have been leaving school anyway, and Catherine had to study. "Can I do one more quick thing before you change back?" she asked, almost sounding like this was some magic spell that would soon be undone. "Anything" I said (and meant it). She told me to sit on the edge of the bed and close my eyes. I obliged, wondering what was coming next. She stood in front of me and lifted my chin up like when she was doing my make up, but instead of a makeup brush or lip gloss applicator, I felt her nose graze mine, smelled her sweet perfume, and finally felt her soft lips press against mine for a few seconds. I was enveloped in her gentle aura. I had butterflies in my stomach. My little caged penis twitched in its shell, and I felt just a few drops of wetness escape into my panties. It was the closest thing to a release I'd had all week, and it felt like the consummation of all the unbearable sexual tension that had been building. She slowly broke the kiss but kept her face a few inches from mine. "I always wanted to try kissing a girl. Don't tell anyone okay?" I promised her it would be our little secret. I changed back into my boy clothes (with the exception of my panties), and we hugged before I headed home.
Later that night after dinner, Rebecca texted me:
"BABY I miss you. Catherine showed me the pic. you make such a gorgeous girl. you're like, hotter than me. its actually kind of fucked up haha"
I replied saying no one is hotter than her, but that I had a lot of fun dressing up with my friend. I even told her about what we did to the jocks. she replied:
"WHAAAAAT NO YOU DID NOT! LOL are you serious?"
I told her I was indeed serious, and said something about how dumb and thirsty those guys are.
"omfg baby thats fucking hilarious. those guys WISH they could fuck my boyfriend lmao. hmm maybe I'll pimp you out and make a bit of cash on the side haha. what do you say slut? wanna be my hooker boyfriend?"
I laughed and said I didn't think they'd want to fuck me anymore once they knew I was a boy.
"honestly when you look like that, I don't think they'd mind haha"
We went on chatting and catching up on how our weeks went. Then she told me that her parents were away all day tomorrow and Sunday, and that I should come stay with her for two whole days. I was thrilled of course.
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