Gay For Pay & Crossdressed
Written by Anonymous-Prefered, on 2019-02-28, genre trans
Gay For Pay & Crossdressed
There was a great guy I knew who was about 10 years older then me. We had worked together for many years for a major department store in a major city.
Let's call him John. One day he told me he was gay but I already had figured that out.
This takes place about 25 years ago when a time came that I became separated from my job and was on the skids. I was living on unemployment checks and staying with my parents.
My parents barely got by themselves back then. My Dad had been hurt and couldn't work anymore and waited for his case to settle. My unemployment money basically went towards paying the rent most weeks. Things were tight.
John was ambiguously gay no one else really knew if he was or not. John really liked me but I was into women and just couldn't reciprocate his feelings like that. We had become pretty close regardless of this and shared many secrets while working together over the years.
John had a boyfriend but said their relationship was very sour and that they never had sex anymore at all. He wanted to leave but his significant other threatened suicide if he did so. John still had his own apartment and a room at his boyfriends condo.
I met John's other a few times, a spoiled rich asshole who I did some computer consulting for. He never worked a day in his life having inherited his wealth fairly young upon loss of his parents. He wasn't very self sufficient.
Talking on the phone one day I was telling John how bad things were at home making the rent and a deal was struck. After being friends for almost 6 years we would have sex. I would be his love slave, basically gay for pay.
Having no skills that way I would be paid based on my willingness and seeing things through with him. We agreed to just feel our way through the situation this first time. After a week of talk over the phone, the day finally had come around.
John opened the door in a lush white robe and matching slippers. After a nervous greeting I was ushered inside the hallway. He looked around nervously and closed the door.
There were some chests, shelves and closets and a few steps that led down to his basement apartment. It was away from the rest of the building and I followed him inside.
John was really intense, he licked his lips in anticipation like a cat about to make a kill. He opened the bathroom door and I entered it. I caught a glance of myself in the mirror and saw how nervous I looked and quite honestly, I could have puked.
No matter how calm I tried to be I was fairly rattled and scared. Okay then, this was real and it was now going to happen. We had an agreement worked out and it was now on me to keep my end of it.
He hovered outside the door and asked if I was alright. I nodded and slowly closed the door. There was two XL lingerie outfits hanging on the towel rack. Both black, new with tags, lacy and mostly see through.
One was Christian Dior as I recall and not cheap. There was also a package I thought was black pantyhose but it was actually thigh high stockings with thick bands on top with a few gold threads as accents. I always wanted to try them, for my own sexual release purposes masturbating.
I kicked off my sneakers and sweats, everything for that matter, keys and wallet also and handed them out the door just as we had agreed to. John took them and secured them outside somewhere.
I don't know where he went to maybe out in the hallway or in a drawer so there was no changing my mind now. I had to see it through to get it all back, I was his now and had to trust he would keep to his end of the deal.
The first item I put on was the thigh high stockings. I had seen it many times in movies, I had jerked off in pantyhose a few times and these felt good on my legs in the cool air of his basement apartment.
My legs weren't shaved, I could never pass as a woman but they hid my hair well with it being see thru only near my upper thighs. I am not a very hairy guy anyhow. I liked the way it looked and the compression felt so good on my legs. Wearing them really made me feel kind of sexy too!
I figured out the lacy thong next which was pretty snug in the rear. It was not made for a chubby male but it was part of the Dior set I chose to wear for him first. Next I tried on the lacy pullover which was a fairly sheer spaghetti strap type tank top.
It was really very stretchy and pushed my man boobs up and together. They really looked like breasts about the size of sideways lemons and showed my large nipples underneath through the sheer material.
I was really scared, turned on, very curious, simply overwhelmed and felt pretty cheap all at the same time but I really needed the money and that was the end all of it. I had already borrowed from a few different people and didn't have any recourse left.
Suddenly, there was a knock at the door. I got myself together mentally the best I could and cracked the door open to peak outside. Don't laugh at me okay, I said and then I just stepped out bravely.
John's eyes were ablaze as he looked me over. He told me he loved me for the longest time and grabbed me and kissed me way to forcefully. I still remember his coarse mustache brushing against my face. I resisted subtlety as I just wasn't into it. I was uncomfortable kissing a man like that and I told him that I couldn't give him the relationship he wanted just sex.
This was a business arrangement, we had discussed it all week at that had to be clear. The womens clothes was a fetish I had to get off and I had told him about it. I used ladies clothes when I would masturbate sometimes over the years had never dressed in front of anyone else like this.
It was kind of a submissive fetish/fantasy and if I was to be his new sex slave it should help me to be in character and as it turns out it really did help me do so.
He had me sit on a weight lifting bench in his living room and tied my hands. I said It's not likely I was going to run away or call for help dressed like this and we both laughed to break the ice a bit. We were both much like deer in headlights so far, kind of rigid but it was new ground for us here having been just close friends for so long.
In our discussions, I agreed to be spanked to comply if needed but it didn't really happen. I called him Master a few times but it wasn't a thing for him and got dropped rather quickly.
He tied my feet next and then had me kneel on the bench on all fours. I complied as he opened and dropped his robe. John liked brand names and had on red and white silky Tommy Hilfiger shorts. He was an Asian Pacific Islander, built, dark tan, well defined abs but very slender unlike me on the pale, blue eyed, white, heavier side.
He said don't look and stood behind my ass. I put my head down not sure what was next. I could tell he was jerking off and he also slapped my ass with his stiff cock quite a few times. He then knelt and put his face deep in to my ass crack.
He would mutter stuff like damn, shit, fuck and made an elongated slurp noises. He breathed deeply, beating his meat and looking me over. Don't look at me he said again catching me looking back and quickly got a scarf and blindfolded me while I was still tied and left on the bench. He had taken some photos and I begged him to delete them, no evidence and he said he did.
It seemed like an eternity balanced there like that on display and then the uncomfortable g-string was suddenly pulled a side and his tongue began to explore my ass liberally and he started rubbing my semi hard junk through the tight thong.
After a while his tongue got more aggressive as it went on and on and he just kept eating my ass out. I couldn't help but wonder if he was going to fuck me like this. I wondered if I would truly go that far. Being tied up so tightly and balanced on his weight bench I certainly couldn't stop him.
I must have moaned or tipped off how good it was becoming for me because he said to me fairly roughly not to cum. Tell me first, don't you cum okay. I could hear and feel him working his own cock furiously and rubbing it all over in my now ecstatic ass crack. I liked it more than I wanted to ever admit.
Truth be told right there and then, I just wanted to fuck!
Then he said something like oh shit and I felt several globs of hot cum hit my ass cheeks, quickly cooling off and running way down to my ballsack.
The scarf was falling off now and I easily shook it loose and I saw him run to the kitchen, grab a towel and he came back to wipe me off. Sorry he repeated several times and I said it was ok, that's what I am here for right, to be your girl?
He liked that comment and he wanted to suck me and taste my cock but now balancing on my back tied up proved far too problematic. My feet were released and retied up to the bench bottom itself and my hands to the weight bar racks after I had flipped over.
With the thong now pulled down and stretched between my knees, exposed and helpless my cock was fully erect in the cool air and John beat it against his warm tongue. He really took his time licking it and lapping up my pre-cum, squeezing my man boobs now and then and toying with my nipples. I had actually shaved them for this.
It was glorious and wow as much as I love women I didn't want it to end to soon. Don't cum yet he ordered loudly and if I wasn't so nervous I may have already done so. I was now orgasmic arching over the bench as he played about with my cock and balls in various ways and rubbing my ass.
He said he loved getting straight guys and wanted to suck me for a really long time. Next he untied me again and led me to his bedroom via my all time high rock hard dick, like it was a fucking leash! It was a killer move and it was so swollen it hurt a bit like it was busting at the seams. I really wanted to cum so badly I could have begged for it or paid him for it.
The thong was now around my ankles as I shuffled my way into his bedroom. The room was mostly darkened with a huge bed and lavish comforter set. A small ceiling high slotted basement window let in some of the mid morning daylight.
He dropped his shorts to the floor and I got the full view of his cock. Much better than mine even with his now mostly limp, semi erect condition having just shot his load and it was shaved clean as well. I had seen glances of guys cocks over the years unintentionally but not like this. This was presented for my own personal perusal and completely shaved at that.
I was then turned around and pushed against the bed semi bent over. I saw lube, lotions and condoms on a side table. I don't want you to see me ok... This time he did a better job of it and blindfolded me pretty decently with a scarf and resecured my hands tightly in front of me.
He ate my ass out religiously and worked his own cock again furiously just as before. My ass felt so damn good I found I was actually pushing back at his tongue and I almost came from it untouched and suddenly, I just hopped up on the bed submissively without instruction. Seconds later something new was added, a makeshift gag he stuffed into my mouth to my suprise.
He said whether it was true or not, I needed to be very quiet his upstairs neighbor was very nosy and knocks for any odd noises she hears. She is always checking up on him and it is so annoying and invasive.
I just went with it. I felt something cold in my ass crack it was lube and his fingers began to play with my asshole. I was now trembling like a leaf. Told to relax several times a finger found it's way inside me briefly.
After what seemed to be a long while the slight pain, weird sensation went away and I relaxed enough that that he decided to give it another try. I did as I was told and kept my ass up high and my head buried in some pillows.
He had worked one finger in to two and maybe even up to three I guess. It took a while to get there and then a long silent pause and I knew for sure what was next.
He said don't worry he had a condom on and pressed his cock several times against my virgin hole to limited success. I squeezed him out or reactively pulled away but he just got more excited by it. My God it's so fucking tight he said. I knew he was determined.
After some more brief and awkward efforts, I found that I was now on my back, legs up over his shoulders. The stockings against his skin felt great and I felt very feminine, aroused and complacent in this position. He sucked my toes through the stockings and I found I was soon holding him with my legs wrapped tightly around him, wanting to be fucked so badly. I was like another person entirely and for that moment as promised, I was absolutely and completely his.
He kept calling me his girl and then said that he loved me so much. He was now inside me and fucked me lightly not wanting to come out again and kept working his cock deeper in to my virgin ass, slowly spreading it open more and more.
When he finally started fucking me harder my man tits shook wildly with his thrusts and it felt good. I was so turned on by all these sensations but he didn't last long. It was only a few short minutes and he came really hard grunting as he held down my tied up hands just over my head and his other hand and body weight holding down my shoulder roughly against the bed.
I could see his sweaty tan hairless chest from under the blindfold looming over me. I remember it getting just a bit rougher as he ejaculated with his cock inside me. John suddenly got manic, kissing my neck, sucking on my armpits and nipples wildly, even biting at my lip a few times.
When he finally pulled out of my ass my legs were locked around his torso tightly and he told me the condom had pulled off him and was still inside my ass. He collapsed on to the bed next to me breathing heavily.
I made some humming noises and he took the gag out of my mouth. It was actually the thong I had been wearing! Shit, you are so good he said. Not likely I replied and he said no it was great.
I said I felt very exposed now, feminine and really submissive he said that was good because now I was his slutty girl. And I said just for you John and we must keep it all secret from everyone and especially my family.
He asked if I wanted to cum but that straight guys don't stick around after they cum, it's always right out the door. I said I wasn't going anywhere dressed like this remember? We had a good laugh and then he casually just started to suck my cock which had went limp after or during my hard fucking.
I quickly got hard again inside his mouth so it was no issue and I could see the top of his head with the makeshift blindfold now all loosened up and falling off again. I remember looking at my legs in the dark stockings as his head was between my thighs and being so turned on by it.
Then he really went after it. I came like crazy rather quickly and he said no, not yet a bit angrily, to soon! He sucked me a bit more after it had stopped pumping out my spewing jizz. He just kept going until it was far too sensitive for me to continue.
And he was right, I wanted to get dressed and go. He held me in his arms on the bed and untied my hands. We were very sweaty and I suddenly turned on myself a bit mentally. Things like, what was I doing? I mean, I was now officially a gay whore. I was a gay mans personal prostitute. I straightened up my outfit the best I could and John had me roll over to get the condom he left deposited inside my freshly fucked asshole.
When the condom was pulled out I felt like I had to go badly and went to the bathroom quickly. My ass was slightly bloody. He asked if I was okay and I told him about it. He was very apologetic.
I told you I have never done this before, I muttered. He had on his robe again now and just kept apologizing endlessly but it cleaned up quickly and besides being a bit sore now, I was basically okay.
After a few minutes rest sitting down I was ready to put on the next outfit. Same stockings as before and the new outfit was quite similar to the first but more like French cut panties. Far more comfortable and stretchy then the thong was.
The top was loose and a thicker black lace. Lets just relax he said and held my hand walking back into the bedroom. He hugged me and kissed me deeply a few times I just allowed it. There was some tongue but I had to turn away when he did it.
I told him I can't give you this John, please don't get hurt or mad at me. I want a life and family with a woman. I have never once been attracted to a man. He said he knew that and it was all okay. He playfully called me his girl again and I said no more like your dirty little slut, well not so little and we laughed.
He said he liked me being heavier, fat men were okay with him and he said I had a nice dick, good taste and that my dick was big and wow so much cum. I always did have a big load and had been told so in my sexual exploits elsewhere but I felt like he was just being kind about my performance.
He talked a bit more about a lot of things as we laid on the bed, snuggled up together and I decided to try and suck his dick. He said no that it was okay he didn't expect it from me but I said I really wanted to do it, just for him and I meant it. If I am going to be your girl for now on, I need to learn how to please you all different ways right?
Well, I choked a lot at first, my gag reflex was so strong. I could taste the condom a bit too. He had his eyes actually rolled back as I finally found a way of taking his thick cock head into my puffed out cheeks and tonging and sucking on his shaft, he kept saying oh shit repetitively. He stopped me soon after maybe for too much teeth or something but said I had a definite style.
My corruption thrilled him though as he had made quite a gay sex slave out of me this day. I stayed with it and tried again but he never got fully hard-hard or came soley from my efforts.
Next up he had me bend over the bottom of his bed holding my wrists crossed in the small of my back. Yet again, he said to me not to look. I agreed, but said no rope or blindfold this time. I would totally submit to him freely as we discussed. John beat his cock on my big sissy ass like it was for an actual spanking and jerked himself off at a hundred miles per hour. He rubbed it up and down my ass crack.
Suddenly, I was pulled down to my knees at the foot of his bed. I instinctively turned around quickly, my mouth was quickly opened by his cock rubbing through against my lips as I he worked his own meat furiously. I opened wide and waited and was rewarded with his hot cum squirting in to my waiting mouth. Some of it was running down my chin just a bit and some shot way deep into the back of my throat.
Not sure if I should swallow I held still as it lingered in my mouth kind of melting away and I suddenly just swallowed it as he looked on at me.
The taste was very different from my own sperm and I could smell the smell of sex in the air. His dick still in my face I just stayed there kneeling almost as if in shock. The taste lingering on in my mouth. I liked his tip clean meekly and it got real quiet.
He said why did you do that, suck me before? I said, I just wanted to make him happy and do everything he could want from me. Compliance was a major part of the deal after all and I need to learn and hoped I did good. He said sucking him was really a surprise and it was great, that I was really terrific but he seemed weird about it to me.
I used a towel and cleaned my face and John handed me a plain white envelope with a lot of money in it. More then a full week's pay back then I found out later. I knew he was being very generous, I didn't count it there. I just looked quick and thanked him. He said it wouldn't always be like that, I said ok, I understand and thanked him again also for his patience with me doing all this.
We got dressed and then had lunch nearby, John paid. I had the second outfit on still under my sweat clothes as our little fun secret. I went home with it on thinking about all I had just done and experienced. Thinking back I think he may have kept my underwear.
We had several other various sessions and many different rendezvous places with both of us keeping it top secret from everyone we knew. I helped him act more straight at times to blend in to crowds since he was still closeted.
One day it was a few naked blow jobs and my ass getting fingered in a local park, watching others have sex there, storage locker sex, my ass fingered on a bus or train, another time I changed inside a dark theater into a hoochie mama cut up black skirt, white top, wearing jet black thigh high stockings with a white satin panties and bra set for the entire duration of the movie.
We both sucked some dick and I came in his mouth several times while watching the film. We went to the movies a lot! Even seeing the same ones over again for our romps.
I wore a lot of different eBay lingerie. I mostly now got it my own for our encounters and sometimes just pantyhose play and took many public sex chances being John's girl. But our sessions had gotten typically much shorter though. Anal sex was now getting pretty rare. I would sometimes lay with him after things but most times I now left quickly after shooting my load for him or got dressed normally quickly and did other things.
It all came to an end one day when he wanted a gay police officer friend of his to enjoy me fully over at his place. I told John I was only his girl, I did this for him and felt odd dressing for someone else. I was worried about what this guy knew about me now also.
I was guilted over all the money so far and bullied a bit about things, I finally said okay after prolonged badgering. He told me just imagine my ass being eaten out as my cock was sucked by his friend at the same time. Then he wanted to watch me get fucked maybe handcuffed to the bed.
At times, John was getting to rough with me and I was starting to feel like I was being raped or something. I hated the forceful kissing. He was stronger by far and pinned me down more than once in doing so. I would give in a bit and kiss a little and he would French me for a while when he could.
I felt really bad for him, I knew that it was his frustration he really wanted me as his other, to say I love you back and to live with him as his boyfriend in the future when he broke up. It just got worse and worse as time passed.
I was back on my feet now and had my own place but the sex continued now and then sometimes for free but he may have feared he would loose me and grew distant.
One time, I wore a white lace lingerie dress that he pulled up over my ass. I had cum without my cock ever being touched as he played with and ate my ass out royally. He really flipped out on me and got so angry. He licked my cum off the sheet. To make it up to him I submissively and apologetically ate his ass out, a first for us.
He then jokingly wore the lingerie I had worn as I sucked him for a while but it felt like more of a mockery. He never came no matter how hard or long I would suck it. He needed his own speedy hand job to do so. I asked him to take it off and he quickly did.
He began to yell at me if I showered before he saw me. He would call to see if I jerked off or had sex with a woman that day or week. One time I had, so he took off work came over and stripped me, laid me out on the floor and sucked my cock in sheer jealousy. He wanted every drop of cum for himself.
Then we moved on to my bed he was laying on top holding me down kissing me hard. When I said it was like a rape he got more excited and got hard inside pressing against my ass cheeks and partially entered me as I struggled. I was pinned to the mattress in missionary fashion but then John jerked and came all over my belly. I got up behind him to fuck his ass in to submission a bit angrily and he willing complied but I couldn't maintain it I was not attracted to a man like that, never have been and stopped.
It was getting way to weird and now as I said now this police guy thing was looming. I was talked in to it but when the day came I just chickened out and cancelled. I was wearing some lingerie under some sweat clothing during the call, it was that close I was just about to leave to meet up.
I knew it meant me being spit roasted, eaten out and blown, maybe possible double penetration, swallowing their joint cum, being watched as I got fucked by a stranger. I might not even get to see this guy, it was something he wanted me to do for him and it was just all getting to be to much. I had girls around I was in to and happy with. Besides, this guy could be diseased or something, who knows?
We argued on the phone a few times that day and I gave back the lingerie he had bought over time, even my own purchases from eBay. When I next saw him, I had it all ready in a brown paper bag and I ended things. I worried about possible blackmail at first he may have pictures but John was still in the closet among mutual friends and he never did do that.
I would still go to see John on rare occasions or vise-versa. He really was a good guy, very generous, always giving gifts to people, a big heart, everyone loved him. I even gave him some little freebies to help him cum after that for all he had given to me. He was very unhappy in his own relationship.
I told him he could stay over and I wouldn't say no to anything at all until sunrise for everything he'd done. He could cum all night long no permission needed. But, it was really over for him now and he said it was now to hard to see me without me commiting to him fully. He wanted me to say I love you and be exclusive to him , share the future and I couldn't do it, so he left.
It has been many years since I last saw him and unfortunately, it was at a funeral but we had a brief talk and shared a long hug. Sadly, he still had his same long time rich boyfriend guess he never moved on from that.
I am currently happily married by the way with a family but I still think of John on occasion and back on that time in my life without remorse.