Every Man Is A Little Bit Gay
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I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lips, same height as me. Musical tastes in common? Check. Reading? Movies? Check and check.
Polyamorous. Well. I've been single for a while at this point, and I've dated around a fair bit, so it didn't seem like a troubling thing. Besides, it said she was single anyways at the moment. I looked over her answered questions and found all sorts of fun things: she seemed to be quite sexually open for one. For another, she seemed very... take charge. I've never been the most forward guy around, but hey, time to try new things. I scrolled through her pictures again. She had a nice smile, and wasn't shy about showing some skin. Or all of it.
Now, she was definitely out of my league. A higher education to boot, but I wasn't that far out of her league either. I don't hit the gym more than a handful of times a month, just enough to keep a little bit of definition, which isn't as easy as you'd think at 5'11. I keep my hair long enough to pull off the whole messy hasn't shaved in two days thing quite well, and it's gotten me places where I could use my dick. No giant, but a decently thick six incher. I have a sweet gig in an IT department, and the money was ahead of the few friends I had around my age.
It was several days later, virtually forgotten, just another woman who didn't respond. Until she did. We chatted a bit, which led to a date. A date that went well, at a comedy club. She was actually better looking in person, and the confidence I saw in her profile was definitely there in real life. I didn't hesitate to pay for everything, I didn't want to be stingy, and she'd obviously dressed herself up a fair amount. This led to more texting and another date. I hadn't made it to second base yet, but she knew how to keep me on her finger. She was interesting and enjoyed to flirt, but not to be caught much at all.
We continued to date for a few weeks, and learned she had been through some rather intense relationships and had done the whole polyamorous thing for a while, but was trying to see if she could do the whole single thing. She had also done the whole kinky sex thing quite a bit more than I had. I'm not vanilla, but she was in another category, that I hoped to experience soon.
It didn't quite go that way. I'd take her out somewhere nice, we'd have a good time, and a peck on the cheek at the end, at best. She'd flirt, and I couldn't help but respond, and my sole attempt to bring up the issue had been quashed quickly. I didn't want to risk that again, so I let her take things at her own pace.
Outside of that, things were going great for me. We were forming a real connection, and after a night at my place, we ended up cuddling and watching a movie. She just kind of leaned into me, and her hand would occasionally find its way to my crotch. My dick would surge in response, it had been almost a year since I'd had sex, and the months of not being able to have sex with her had me at my peak, then she'd stop, and reposition just a bit. This lasted for almost the entire movie. I asked her to finish, but she would just tell me to keep watching the movie, which was by no means an easy task.
A little bit before it ended, she decided to keep going. She had been squeezing and rubbing me through my pants for nearly an hour and a half, on and off, a few minutes here, a few seconds there. I tried to move things to the bedroom, but she told me to just enjoy it. So I did, it's not every day a beautiful woman wants to do kinky shit with you, and moments later I had an incredible orgasm, spewing cum into my underwear. I tried to get up, but she wanted to cuddle while we watched the end of the movie, so that's what we did, in my sticky underwear.
I got up to change once things were over, and once again, she stopped me for what I thought was round two. She wanted me to eat her out, and I started to swell again. She wanted me to keep the underwear on while I did. I was fairly confident in my pussy eating, and got to work. Even her pubic hair was darker red, trimmed and moist. What I thought would be a five minute affaire took almost half an hour of me on my knees in front of her on my couch. She was rather noisy, and any time I paused for breath she would praise me and tell me to keep going. Eventually her legs locked around my head before her orgasm hit her as well as my face. She could clearly see I was more than ready again, but she just said that she liked her boyfriends like that, gave me a peck on the forehead, and left.
Things just sort of escalated quickly from there. We spent more nights each week together than apart, at her place or mine, usually after a night out. We did everything from mini putt to higher end restaurants, new cafes. It was just understood that I paid, hell I would've paid double. Everything was clicking, our humor, our politics and almost everything you could think of. But sexually... Well, I couldn't fuck her.
She loved to tease me, and had a dominant streak a mile wide. She didn't want to be called mistress or anything, she simply liked to be in charge. And get eaten out, constantly. I was so horny all the time that I was more than happy to please her. She would jack me off into her panties as quickly as she could, which usually wasn't long. And then she had me wear them and masturbated me into them. Honestly, I was coming to enjoy this. I had always had to do all the work before, and while I was desperate to penetrate her, I wasn't going to push it.
Instead, I simply embraced what she wanted from me sexually, because it made her happy. It took hours of her edging me to agree to wear one of her dresses though. My will power lasted quite a bit on that, I simply didn't want to do it, but she was certain she could convince me. She just wanted to be in charge, sexually, and this was a fun, kinky thing none of the other guys let her do. Once my head was buried in her pussy, she would ask if I enjoyed dressing up like a girl to eat her out, and I would shake my head and keep going. My face basically smelled like her vagina by the time she had several orgasms. She asked me to stand up, and asked again if I liked dressing like a girl for her, and when I shook my head sideways, my loose shaggy hair swishing, she would point at my erection pushing out of her dress. It was embarrassing and hot and she wouldn't touch me until I told her that I did enjoy it, then she masturbated me through the dress.
A few months later she had me dressing up in all sorts of outfits, or lingerie or even jocks, licking any part of her she wanted on command and wearing panties to work. While it wasn't my favorite thing in the world, I was questioning what I had been missing out on with previous girlfriends. I quite enjoyed being the submissive one. In fact, life couldn't have been better, because shortly after she wanted to show off my skills. She had a couple of flings with girls previously, and she knew this one would love to make use of my wondrous talented tongue.
So when I bragged to my friends at work about having a threesome, they didn't know that I spent hours eating them out in frilly lingerie with a collar around my neck. They don't know that I would warm them up with my mouth, then watch as they took turns pleasuring each other with dildos as I masturbated in the corner of the room, wondering why it couldn't be my dick. Sure, I wasn't as big as some of those dildos, but I was growing more resentful.
I had never really stood my ground on any issue with her, and while things were comfortable, I really wanted to get into her pants with more than my mouth. When I brought the subject up, she seemed understanding but exasperated. That was a very long week, as I was determined to hold my ground, but she seemed more distant towards me. I was terribly worried I was doing something wrong, and three nights apart was all it took, I felt I needed her that much. I apologized profusely even though she hadn't really said anything. Instead, that night, she had me dress up in frilly pink lingerie before getting her pussy nice and wet before stopping me and handing me a thicker eight inch dildo. My heart sunk and my dick throbbed.
She didn't need to say a word as I slowly pushed it inside her. Because she knew how badly I wanted to fuck her, instead she was going to have me fuck her with a plastic cock noticeably bigger than mine. It was humiliating, and to make things clear, she let me know how good it felt to be stretched out, how she missed being filled up regularly. She enjoyed a powerful body shaking orgasm, and once I slowly withdrew the dildo, her pussy closed up. She had me carefully lick her clean, then took the dildo and pointed it at my lips. I stared at it, and I could tell she wanted me to suck it clean. Her other hand cupped my penis through my panties. My hips bucked instantly, and she pulled back and had me hold the dildo. I ended up fellating it passionately as she let me hump myself against her cupped palm. She looked none to happy to have a wet palm once I spurted, and wiped it off against my cheeks.
Things seemed to change then. We still did the normal couple stuff. I'd met some of her friends, she'd met some of mine, but when we were out, she seemed to be naturally deferred to, even though I was clearly her boyfriend. She would send me pictures of woman's clothing she thought I'd look good in, and would ask which color I thought looked best. It was the best sex I'd ever had in my life, despite not being able to have intercourse, and truth be told, I was starting to like enjoy it more than I thought possible. I wouldn't have done it on my own, but I was enjoying the cross dressing and how it turned Wendy on, and the humiliation was addicting. It made me incredibly hard, and I was glad no one had much of a clue what was going on. Outside of her perhaps being a bit more dominant publicly, it was going great.
Unfortunately, as much as I wanted to keep her to myself, I knew that wasn't going to be an option. I was working her with a new vibrator she had me buy her, when she declared it good, but not good enough, she really needed the real thing. My heart leapt for a moment, and she must've seen it in my face, and tilted her head sideways and gave me a sad smile, "No, not yours." It was infuriating, and I pulled my panties down and gripped my dick, defiantly.
She looked over at me, got up and got out the first dildo I'd seen her use, holding them side by side and said "The dildo is actually bigger than you. You're not tiny, but I know you'd disappoint me that way. Jeezus, stop crying you little sissy. Look, you're all hard, because I know you're enjoying this. You're a great boyfriend, but honestly, you're not much in the man category." I couldn't let go of my dick, it was so hard it was painful. She was speaking so patiently and calmly like this whole situation was normal.
"I told you I was poly. And that means I'll have other partners. I won't have with them what I have with you. I was trying to do the whole normal relationship thing, but... I just need more. You're great, but you just can't satisfy me that way, and a few others. Honestly, you're not the type I usually go for, who are generally a little manlier. But, I do love having fun with you. It turns me on so much baby." She paused for a moment, getting some lube, and dripping it onto the dildo.
She stopped in front of me, holding the lube coated dildo in front of my eyes, "You know where this is going, don't you?" I nodded, and she looked down at my straining, once proud erection, "And that's why I can't see you as a man. You know where this is going, and you're excited." I didn't try to stop her, her prior ambivalence replaced with a sort of conceited joy, and moments later she was behind taking my anal virginity. I want to pretend it lasted long, but it wasn't even perhaps twenty seconds. A few thrusts as I tugged one out into my palm while my ass was filled for the first time. The complete shame of the situation had me blasting multiple loads and it splattered six or seven times and I was actually panting. The rush of my orgasm left me quickly, and I felt the dildo slip out of my ass onto the floor.
She walked in front of me, dried tears on my face and told me to lick up my own cum. I didn't want to, but what do you do in that situation? Well, in my case, I licked my palm, sucking on parts, sucking my fingers clean, a cringe when I needed to swallow. She seemed well pleased with herself, and had me use the eight incher on her.
Things changed from that point. She would remind me frequently of my inability to please her with my penis, and that's why she needed real men from time to time. We agreed, to avoid any confusion with our social circles, to let everyone know we were in a polyamorous relationship. This garnered me a bit of attention, some thought I was trying to be a playboy, while others thought I was crazy to share a woman like Wendy. Most though, were jealous, which I found I quite liked secretly.
Our relationship changed in ways I hadn't imagined. We still slept together, but we snuggled closer now. She wanted me clean shaven, everywhere, so I learned way more about personal hygiene than I'd ever expected, but it did make the stockings and panties much more enjoyable. Now she would complain about my wardrobe, and to make sure I was watching my weight. Well, that was fair, she was in great shape, and dressed to show it, so why shouldn't I? I changed my diet and started jogging almost daily. I truly wanted her to be happy, and realized I was incredibly dependent on her. But she seemed to need me as well.
I mean, who else would help their girlfriend pick out a guy to fuck her the way he couldn't? She'd gotten one of those dildos that you can stick against a flat surface, and lined it up with my ass and had me anally pleasure myself while she showed me pictures of potential guys. "This one? Not much in common, but he's got a nice wide chest. And that cock he's packing looks so nice pressed against his underwear." She had a comment for each and every one, and I saw way more dick's than I'd ever expected to look at. Eventually she picked someone who had a thick seven and a half inches of meat.
I knew it was for real, but it was almost surreal when she had me wait in her living room while this guy came over and had sex with my girlfriend. I wasn't dressed up, but I sat there, quietly, listening to what sounded like one hell of a rough fucking. She never made noises like that with me. The guy gave me a wink as he left, and Wendy had me come into the bedroom and suck his cum out of her pussy. I didn't even bother to protest, I simply crawled in between her legs and got to work.
This wasn't a regular thing, but over the next couple of months she found three partners, and she usually had them over about once a week each. At first I would just dress up and wait outside, but eventually with some of them, I would end up in the room, watching. Not everyone wanted to see me, so for them I just stayed outside but all of them were significantly bigger dicked than me. I saw most of them, and my confidence shot down. She could have huge massive manly cocks whenever she wanted, there was no way I was ever going to compete in that category. Things took a turn for the crazy one night. I was painting her toe nails as she was flipping through possible new partners, when she asked me for my opinion on one. I couldn't hide my reaction quickly enough, and she coaxed it out of me: it was my bosses' boss. I didn't know him personally, but I knew of him, maybe said a few words.
Wendy was ecstatic. Myself, significantly less so. She scrolled through his pictures, and sure enough, he was well endowed, with a pair of hairy balls that wouldn't fit in my hands. He wasn't particularly attractive, and he was in his mid-forties, but he was definitely that manly type of man. I put my foot down. Some people at work knew that I was in a polyamorous relationship, friends did, but no one knew much about the sexual side of things. I was concerned how I would be seen at work if it got around that some higher up was pounding my girlfriend.
She didn't want to let go of the idea, at all. She simply resolved herself to change my mind on the subject. She decided that I didn't know what I was denying her, so she would try and show me, bringing me up to the eight inch dildo. She had me bend over while wearing a skirt, slowly working it into it me. Even though she took her time, it was painful almost, but once she found the right angle, I couldn't help but leak cum. "See? Don't you want me to have this? You like nice thick things shoved in you, so do I. I want his big thing shoved in me. You want to see his profile again? He's bi, and he's quite kinky. I think he'd be interested. Who knows what could happen? Want to see some pictures of his cock again? I sure do." she said it so casually, like she wasn't talking about having someone I know fuck her with me crossdressing. I had to agree before she would continue to cram the dildo inside me over and over until I splattered the surroundings with semen, and I was really getting into these anal orgasms.
Internally, I was feeling like a mess. I was pretty OK with being the submissive one in the relationship, and sex was amazing if rather humiliating. But I couldn't deny that I was coming to greatly enjoy having those dildos inside me. I would see her other partners come over, and fulfill her sexually in ways I never could, and my dick would react very positively. What does that mean about me? What does it mean that I would stare at strange men's cocks in silence as they provided her with what I could not. I was thoroughly enjoying her teasing and show me potential partners.
So it's not surprising that soon after that I sucked my first dick. One of the men who didn't mind me watching eventually didn't mind me getting involved. Wendy had worked some magic on him perhaps, but mostly on me. She sat me down, and told me that this guy wouldn't mind me "getting him ready" for her. I started feeling the arousal the moment she said it, asking what exactly that meant, so she spelled it out for me: "Y'know when I turn them on? And get them all nice and hard before they can start pounding away? Well, you'll do that! Saves me a little effort, and it's pretty kinky. It'd turn me on a lot to see you on your knees getting a cock ready for me."
I explained to her that I wasn't gay. She knew that. "I don't know, honey. You do enjoy dressing up in women's clothing and having dildos in your butt. It's why I can't see you as a guy. We've been together a while now, and I can't imagine any guy going this long without managing to stick his dick in his girlfriend. But don't think of it that way. You're a failure at being a man, and you still have a girlfriend. Don't you want to make it up to me? By getting a real man ready for me? Get him all nice and hard and you can enjoy watching him give me what you can't. Then you can gobble up all his cum out of me, doesn't that sound hot?"
She apparently knew my weakness, and with just a few phrases, I was agreeing. Or my penis was agreeing. She had me practice on her dildos, because she didn't want me to embarrass her. No boyfriend of hers was going to sc**** his teeth on a dick or cough if it got too deep. She even got me all dressed up in one of her own outfits for the occasion. My body was losing some definition as my weight dropped slowly and my regimen of keeping hairless had me feeling decidedly less masculine.
That said, I felt a lot less masculine with my hands on another guy's junk. It felt soft and squishy and warm, and I wondered what I was really doing until it started to grow in my hand. That made my heart rate skyrocket, and it wasn't long until I was jerking on a cock that wasn't mine. I was embarrassingly erect, and Wendy watched and coached as I provided my first blowjob. She didn't let me off, and after only a couple minutes had to tap me several times on the head to get me to stop, and go to my spot in the corner as he mounted her. I creamed my panties near instantly, and watched the whole ordeal. He left quickly, and I did my job by eating all of his cum out of her.
This became a weekly occurrence, and I got very used to feeling up that cock. I would catch myself daydreaming about it and wanting to use it to prove to her how far I was willing to go to make up for my failures as a man.
This became a problem a few months down the road. I was still not keen on the idea of her hooking up with my bosses' boss. More so, the changes in my appearance, how I dressed was sparking new ideas in new people we met. Despite being very hands-on in public, it was never anything overt, but obviously people saw something with us. Privately, she would inform me that some of the people we met, and even a couple of her friends were simply assuming I was her gay best friend. I can see why they might think that, while we were out, even though I was paying for everything, she definitely was taking a bit more of a dominant roll, and I never did anything to challenge it. The idea stuck with me though, and I did not enjoy it at all.
This eventually blew up into a large problem, as she thoroughly enjoyed teasing me about being gay, which I would deny, even if I had sucked a cock not an hour before. I put my foot down rather forcefully on a specific occasion. It bothered me for some reason, and I may not have been much of a man, but at least I could draw this line. I did what I did for her, not because I was gay.
Wendy did not take it very well. She became more aggressive in our sexual play in response. She would only use the eight inch dildo on me, teasing me with it. Sometimes, she wouldn't even need me to dress up, she'd just request I bend over, lube up and plug my ass with dildo. She'd remind me of how hard I got when I was sucking dick for her. Right when I was on the edge of cumming, she'd drop a line in about how only gay men get off from things in their ass. My orgasms were amazing, every single time she did this stuff, and when I masturbated on my own, well, let's just say I imagined other things than a dildo in my ass.
It was masturbating on my own that eventually did me in. She was relentlessly with her teasing about being gay, and one night I told her flat out I didn't need a dildo in my ass to get off and was more than happy to masturbate into my panties for her. She kicked me out of her apartment instantly, and I was crushed.
We went days without talking, she wouldn't answer any of my calls or texts. I was frantic to make things up with her, but eventually she agreed to see me that weekend. In the days between then, I found myself masturbating to being willing to let one of her men fuck me. I had some pretty intense orgasms, but instantly after I would clean up and do my best to ignore what had just gotten me off.
Regardless, I was certain I could sway her over to my way of thinking without having to take that plunge. I had no clue what was coming up next.
Polyamorous. Well. I've been single for a while at this point, and I've dated around a fair bit, so it didn't seem like a troubling thing. Besides, it said she was single anyways at the moment. I looked over her answered questions and found all sorts of fun things: she seemed to be quite sexually open for one. For another, she seemed very... take charge. I've never been the most forward guy around, but hey, time to try new things. I scrolled through her pictures again. She had a nice smile, and wasn't shy about showing some skin. Or all of it.
Now, she was definitely out of my league. A higher education to boot, but I wasn't that far out of her league either. I don't hit the gym more than a handful of times a month, just enough to keep a little bit of definition, which isn't as easy as you'd think at 5'11. I keep my hair long enough to pull off the whole messy hasn't shaved in two days thing quite well, and it's gotten me places where I could use my dick. No giant, but a decently thick six incher. I have a sweet gig in an IT department, and the money was ahead of the few friends I had around my age.
It was several days later, virtually forgotten, just another woman who didn't respond. Until she did. We chatted a bit, which led to a date. A date that went well, at a comedy club. She was actually better looking in person, and the confidence I saw in her profile was definitely there in real life. I didn't hesitate to pay for everything, I didn't want to be stingy, and she'd obviously dressed herself up a fair amount. This led to more texting and another date. I hadn't made it to second base yet, but she knew how to keep me on her finger. She was interesting and enjoyed to flirt, but not to be caught much at all.
We continued to date for a few weeks, and learned she had been through some rather intense relationships and had done the whole polyamorous thing for a while, but was trying to see if she could do the whole single thing. She had also done the whole kinky sex thing quite a bit more than I had. I'm not vanilla, but she was in another category, that I hoped to experience soon.
It didn't quite go that way. I'd take her out somewhere nice, we'd have a good time, and a peck on the cheek at the end, at best. She'd flirt, and I couldn't help but respond, and my sole attempt to bring up the issue had been quashed quickly. I didn't want to risk that again, so I let her take things at her own pace.
Outside of that, things were going great for me. We were forming a real connection, and after a night at my place, we ended up cuddling and watching a movie. She just kind of leaned into me, and her hand would occasionally find its way to my crotch. My dick would surge in response, it had been almost a year since I'd had sex, and the months of not being able to have sex with her had me at my peak, then she'd stop, and reposition just a bit. This lasted for almost the entire movie. I asked her to finish, but she would just tell me to keep watching the movie, which was by no means an easy task.
A little bit before it ended, she decided to keep going. She had been squeezing and rubbing me through my pants for nearly an hour and a half, on and off, a few minutes here, a few seconds there. I tried to move things to the bedroom, but she told me to just enjoy it. So I did, it's not every day a beautiful woman wants to do kinky shit with you, and moments later I had an incredible orgasm, spewing cum into my underwear. I tried to get up, but she wanted to cuddle while we watched the end of the movie, so that's what we did, in my sticky underwear.
I got up to change once things were over, and once again, she stopped me for what I thought was round two. She wanted me to eat her out, and I started to swell again. She wanted me to keep the underwear on while I did. I was fairly confident in my pussy eating, and got to work. Even her pubic hair was darker red, trimmed and moist. What I thought would be a five minute affaire took almost half an hour of me on my knees in front of her on my couch. She was rather noisy, and any time I paused for breath she would praise me and tell me to keep going. Eventually her legs locked around my head before her orgasm hit her as well as my face. She could clearly see I was more than ready again, but she just said that she liked her boyfriends like that, gave me a peck on the forehead, and left.
Things just sort of escalated quickly from there. We spent more nights each week together than apart, at her place or mine, usually after a night out. We did everything from mini putt to higher end restaurants, new cafes. It was just understood that I paid, hell I would've paid double. Everything was clicking, our humor, our politics and almost everything you could think of. But sexually... Well, I couldn't fuck her.
She loved to tease me, and had a dominant streak a mile wide. She didn't want to be called mistress or anything, she simply liked to be in charge. And get eaten out, constantly. I was so horny all the time that I was more than happy to please her. She would jack me off into her panties as quickly as she could, which usually wasn't long. And then she had me wear them and masturbated me into them. Honestly, I was coming to enjoy this. I had always had to do all the work before, and while I was desperate to penetrate her, I wasn't going to push it.
Instead, I simply embraced what she wanted from me sexually, because it made her happy. It took hours of her edging me to agree to wear one of her dresses though. My will power lasted quite a bit on that, I simply didn't want to do it, but she was certain she could convince me. She just wanted to be in charge, sexually, and this was a fun, kinky thing none of the other guys let her do. Once my head was buried in her pussy, she would ask if I enjoyed dressing up like a girl to eat her out, and I would shake my head and keep going. My face basically smelled like her vagina by the time she had several orgasms. She asked me to stand up, and asked again if I liked dressing like a girl for her, and when I shook my head sideways, my loose shaggy hair swishing, she would point at my erection pushing out of her dress. It was embarrassing and hot and she wouldn't touch me until I told her that I did enjoy it, then she masturbated me through the dress.
A few months later she had me dressing up in all sorts of outfits, or lingerie or even jocks, licking any part of her she wanted on command and wearing panties to work. While it wasn't my favorite thing in the world, I was questioning what I had been missing out on with previous girlfriends. I quite enjoyed being the submissive one. In fact, life couldn't have been better, because shortly after she wanted to show off my skills. She had a couple of flings with girls previously, and she knew this one would love to make use of my wondrous talented tongue.
So when I bragged to my friends at work about having a threesome, they didn't know that I spent hours eating them out in frilly lingerie with a collar around my neck. They don't know that I would warm them up with my mouth, then watch as they took turns pleasuring each other with dildos as I masturbated in the corner of the room, wondering why it couldn't be my dick. Sure, I wasn't as big as some of those dildos, but I was growing more resentful.
I had never really stood my ground on any issue with her, and while things were comfortable, I really wanted to get into her pants with more than my mouth. When I brought the subject up, she seemed understanding but exasperated. That was a very long week, as I was determined to hold my ground, but she seemed more distant towards me. I was terribly worried I was doing something wrong, and three nights apart was all it took, I felt I needed her that much. I apologized profusely even though she hadn't really said anything. Instead, that night, she had me dress up in frilly pink lingerie before getting her pussy nice and wet before stopping me and handing me a thicker eight inch dildo. My heart sunk and my dick throbbed.
She didn't need to say a word as I slowly pushed it inside her. Because she knew how badly I wanted to fuck her, instead she was going to have me fuck her with a plastic cock noticeably bigger than mine. It was humiliating, and to make things clear, she let me know how good it felt to be stretched out, how she missed being filled up regularly. She enjoyed a powerful body shaking orgasm, and once I slowly withdrew the dildo, her pussy closed up. She had me carefully lick her clean, then took the dildo and pointed it at my lips. I stared at it, and I could tell she wanted me to suck it clean. Her other hand cupped my penis through my panties. My hips bucked instantly, and she pulled back and had me hold the dildo. I ended up fellating it passionately as she let me hump myself against her cupped palm. She looked none to happy to have a wet palm once I spurted, and wiped it off against my cheeks.
Things seemed to change then. We still did the normal couple stuff. I'd met some of her friends, she'd met some of mine, but when we were out, she seemed to be naturally deferred to, even though I was clearly her boyfriend. She would send me pictures of woman's clothing she thought I'd look good in, and would ask which color I thought looked best. It was the best sex I'd ever had in my life, despite not being able to have intercourse, and truth be told, I was starting to like enjoy it more than I thought possible. I wouldn't have done it on my own, but I was enjoying the cross dressing and how it turned Wendy on, and the humiliation was addicting. It made me incredibly hard, and I was glad no one had much of a clue what was going on. Outside of her perhaps being a bit more dominant publicly, it was going great.
Unfortunately, as much as I wanted to keep her to myself, I knew that wasn't going to be an option. I was working her with a new vibrator she had me buy her, when she declared it good, but not good enough, she really needed the real thing. My heart leapt for a moment, and she must've seen it in my face, and tilted her head sideways and gave me a sad smile, "No, not yours." It was infuriating, and I pulled my panties down and gripped my dick, defiantly.
She looked over at me, got up and got out the first dildo I'd seen her use, holding them side by side and said "The dildo is actually bigger than you. You're not tiny, but I know you'd disappoint me that way. Jeezus, stop crying you little sissy. Look, you're all hard, because I know you're enjoying this. You're a great boyfriend, but honestly, you're not much in the man category." I couldn't let go of my dick, it was so hard it was painful. She was speaking so patiently and calmly like this whole situation was normal.
"I told you I was poly. And that means I'll have other partners. I won't have with them what I have with you. I was trying to do the whole normal relationship thing, but... I just need more. You're great, but you just can't satisfy me that way, and a few others. Honestly, you're not the type I usually go for, who are generally a little manlier. But, I do love having fun with you. It turns me on so much baby." She paused for a moment, getting some lube, and dripping it onto the dildo.
She stopped in front of me, holding the lube coated dildo in front of my eyes, "You know where this is going, don't you?" I nodded, and she looked down at my straining, once proud erection, "And that's why I can't see you as a man. You know where this is going, and you're excited." I didn't try to stop her, her prior ambivalence replaced with a sort of conceited joy, and moments later she was behind taking my anal virginity. I want to pretend it lasted long, but it wasn't even perhaps twenty seconds. A few thrusts as I tugged one out into my palm while my ass was filled for the first time. The complete shame of the situation had me blasting multiple loads and it splattered six or seven times and I was actually panting. The rush of my orgasm left me quickly, and I felt the dildo slip out of my ass onto the floor.
She walked in front of me, dried tears on my face and told me to lick up my own cum. I didn't want to, but what do you do in that situation? Well, in my case, I licked my palm, sucking on parts, sucking my fingers clean, a cringe when I needed to swallow. She seemed well pleased with herself, and had me use the eight incher on her.
Things changed from that point. She would remind me frequently of my inability to please her with my penis, and that's why she needed real men from time to time. We agreed, to avoid any confusion with our social circles, to let everyone know we were in a polyamorous relationship. This garnered me a bit of attention, some thought I was trying to be a playboy, while others thought I was crazy to share a woman like Wendy. Most though, were jealous, which I found I quite liked secretly.
Our relationship changed in ways I hadn't imagined. We still slept together, but we snuggled closer now. She wanted me clean shaven, everywhere, so I learned way more about personal hygiene than I'd ever expected, but it did make the stockings and panties much more enjoyable. Now she would complain about my wardrobe, and to make sure I was watching my weight. Well, that was fair, she was in great shape, and dressed to show it, so why shouldn't I? I changed my diet and started jogging almost daily. I truly wanted her to be happy, and realized I was incredibly dependent on her. But she seemed to need me as well.
I mean, who else would help their girlfriend pick out a guy to fuck her the way he couldn't? She'd gotten one of those dildos that you can stick against a flat surface, and lined it up with my ass and had me anally pleasure myself while she showed me pictures of potential guys. "This one? Not much in common, but he's got a nice wide chest. And that cock he's packing looks so nice pressed against his underwear." She had a comment for each and every one, and I saw way more dick's than I'd ever expected to look at. Eventually she picked someone who had a thick seven and a half inches of meat.
I knew it was for real, but it was almost surreal when she had me wait in her living room while this guy came over and had sex with my girlfriend. I wasn't dressed up, but I sat there, quietly, listening to what sounded like one hell of a rough fucking. She never made noises like that with me. The guy gave me a wink as he left, and Wendy had me come into the bedroom and suck his cum out of her pussy. I didn't even bother to protest, I simply crawled in between her legs and got to work.
This wasn't a regular thing, but over the next couple of months she found three partners, and she usually had them over about once a week each. At first I would just dress up and wait outside, but eventually with some of them, I would end up in the room, watching. Not everyone wanted to see me, so for them I just stayed outside but all of them were significantly bigger dicked than me. I saw most of them, and my confidence shot down. She could have huge massive manly cocks whenever she wanted, there was no way I was ever going to compete in that category. Things took a turn for the crazy one night. I was painting her toe nails as she was flipping through possible new partners, when she asked me for my opinion on one. I couldn't hide my reaction quickly enough, and she coaxed it out of me: it was my bosses' boss. I didn't know him personally, but I knew of him, maybe said a few words.
Wendy was ecstatic. Myself, significantly less so. She scrolled through his pictures, and sure enough, he was well endowed, with a pair of hairy balls that wouldn't fit in my hands. He wasn't particularly attractive, and he was in his mid-forties, but he was definitely that manly type of man. I put my foot down. Some people at work knew that I was in a polyamorous relationship, friends did, but no one knew much about the sexual side of things. I was concerned how I would be seen at work if it got around that some higher up was pounding my girlfriend.
She didn't want to let go of the idea, at all. She simply resolved herself to change my mind on the subject. She decided that I didn't know what I was denying her, so she would try and show me, bringing me up to the eight inch dildo. She had me bend over while wearing a skirt, slowly working it into it me. Even though she took her time, it was painful almost, but once she found the right angle, I couldn't help but leak cum. "See? Don't you want me to have this? You like nice thick things shoved in you, so do I. I want his big thing shoved in me. You want to see his profile again? He's bi, and he's quite kinky. I think he'd be interested. Who knows what could happen? Want to see some pictures of his cock again? I sure do." she said it so casually, like she wasn't talking about having someone I know fuck her with me crossdressing. I had to agree before she would continue to cram the dildo inside me over and over until I splattered the surroundings with semen, and I was really getting into these anal orgasms.
Internally, I was feeling like a mess. I was pretty OK with being the submissive one in the relationship, and sex was amazing if rather humiliating. But I couldn't deny that I was coming to greatly enjoy having those dildos inside me. I would see her other partners come over, and fulfill her sexually in ways I never could, and my dick would react very positively. What does that mean about me? What does it mean that I would stare at strange men's cocks in silence as they provided her with what I could not. I was thoroughly enjoying her teasing and show me potential partners.
So it's not surprising that soon after that I sucked my first dick. One of the men who didn't mind me watching eventually didn't mind me getting involved. Wendy had worked some magic on him perhaps, but mostly on me. She sat me down, and told me that this guy wouldn't mind me "getting him ready" for her. I started feeling the arousal the moment she said it, asking what exactly that meant, so she spelled it out for me: "Y'know when I turn them on? And get them all nice and hard before they can start pounding away? Well, you'll do that! Saves me a little effort, and it's pretty kinky. It'd turn me on a lot to see you on your knees getting a cock ready for me."
I explained to her that I wasn't gay. She knew that. "I don't know, honey. You do enjoy dressing up in women's clothing and having dildos in your butt. It's why I can't see you as a guy. We've been together a while now, and I can't imagine any guy going this long without managing to stick his dick in his girlfriend. But don't think of it that way. You're a failure at being a man, and you still have a girlfriend. Don't you want to make it up to me? By getting a real man ready for me? Get him all nice and hard and you can enjoy watching him give me what you can't. Then you can gobble up all his cum out of me, doesn't that sound hot?"
She apparently knew my weakness, and with just a few phrases, I was agreeing. Or my penis was agreeing. She had me practice on her dildos, because she didn't want me to embarrass her. No boyfriend of hers was going to sc**** his teeth on a dick or cough if it got too deep. She even got me all dressed up in one of her own outfits for the occasion. My body was losing some definition as my weight dropped slowly and my regimen of keeping hairless had me feeling decidedly less masculine.
That said, I felt a lot less masculine with my hands on another guy's junk. It felt soft and squishy and warm, and I wondered what I was really doing until it started to grow in my hand. That made my heart rate skyrocket, and it wasn't long until I was jerking on a cock that wasn't mine. I was embarrassingly erect, and Wendy watched and coached as I provided my first blowjob. She didn't let me off, and after only a couple minutes had to tap me several times on the head to get me to stop, and go to my spot in the corner as he mounted her. I creamed my panties near instantly, and watched the whole ordeal. He left quickly, and I did my job by eating all of his cum out of her.
This became a weekly occurrence, and I got very used to feeling up that cock. I would catch myself daydreaming about it and wanting to use it to prove to her how far I was willing to go to make up for my failures as a man.
This became a problem a few months down the road. I was still not keen on the idea of her hooking up with my bosses' boss. More so, the changes in my appearance, how I dressed was sparking new ideas in new people we met. Despite being very hands-on in public, it was never anything overt, but obviously people saw something with us. Privately, she would inform me that some of the people we met, and even a couple of her friends were simply assuming I was her gay best friend. I can see why they might think that, while we were out, even though I was paying for everything, she definitely was taking a bit more of a dominant roll, and I never did anything to challenge it. The idea stuck with me though, and I did not enjoy it at all.
This eventually blew up into a large problem, as she thoroughly enjoyed teasing me about being gay, which I would deny, even if I had sucked a cock not an hour before. I put my foot down rather forcefully on a specific occasion. It bothered me for some reason, and I may not have been much of a man, but at least I could draw this line. I did what I did for her, not because I was gay.
Wendy did not take it very well. She became more aggressive in our sexual play in response. She would only use the eight inch dildo on me, teasing me with it. Sometimes, she wouldn't even need me to dress up, she'd just request I bend over, lube up and plug my ass with dildo. She'd remind me of how hard I got when I was sucking dick for her. Right when I was on the edge of cumming, she'd drop a line in about how only gay men get off from things in their ass. My orgasms were amazing, every single time she did this stuff, and when I masturbated on my own, well, let's just say I imagined other things than a dildo in my ass.
It was masturbating on my own that eventually did me in. She was relentlessly with her teasing about being gay, and one night I told her flat out I didn't need a dildo in my ass to get off and was more than happy to masturbate into my panties for her. She kicked me out of her apartment instantly, and I was crushed.
We went days without talking, she wouldn't answer any of my calls or texts. I was frantic to make things up with her, but eventually she agreed to see me that weekend. In the days between then, I found myself masturbating to being willing to let one of her men fuck me. I had some pretty intense orgasms, but instantly after I would clean up and do my best to ignore what had just gotten me off.
Regardless, I was certain I could sway her over to my way of thinking without having to take that plunge. I had no clue what was coming up next.
Haven
- 08.03.2020
- 31
- 0
