First of all, you need to understand I’m not gay. I’ve never had a gay experience in my life but have had a few fantasies over the last few years. I’m guessing that’s because my sex life with my wife has faded over the years and I’m looking for alternative stimulation.
Just a little background. When I was about 10 years old my older sister forced me into her open bottom girdle and then picked me up and put me over her shoulder and carried me outside the house and into the front yard. I had pissed her off for some silly reason that I don’t remember and this was her revenge. She wanted to embarrass and humiliate me in front of the neighbors and all my boyhood friends. So she carried me across the street and put me down in the yard where by buddies were playing ball. I had nothing on but the open bottom girdle and died of embarrassment as I ran home while my friends laughed at me.
Little did she know that would lead to me crossdressing today. It turned me on so much (not that I knew what “turned-on” was then) but it gave me both a mental and physical rush that I can still remember it to this day. I’ve tried unsuccessfully over the years to recreate the same rush by dressing up in women’s clothes – specifically lingerie and going outdoors but haven’t duplicated the feeling.
My wife knows about my crossdressing and tolerates it but doesn’t endorse it nor does she participate. Therefore, I only dress up when she’s gone for a weekend to visit one of her girlfriends or on a business trip.
In the past I tried to get her to dominate me and order me outside dressed in lingerie and she did a few times but she wasn’t really into it and I stopped asking for it. Since I still craved to be dominated I finally posted a profile on ALT.com.
I had a lot of BS responses but after about two months a serious response came from a man living in a different state. We traded e-mails for awhile then got on Instant Messenger. He pried all my fantasies out of me, called me his slut and I called him Master.
One night he decided I was going to perform a striptease for him via webcam. Well I didn’t have a webcam so he ordered me to purchase one and the next night my wife was out of town I would be giving him a performance.
My wife was going out of town in two weeks so I purchased the webcam and told my wife we could use it when we talked with out of town relatives. She was OK with that explanation. I also went on the internet and downloaded a few striptease videos to give me an idea of how to do a striptease.
For the next two weeks I practiced my striptease in front of a mirror whenever my wife was out of the house. If I say so myself, I got pretty good and was looking forward to stripping for my Master. He already had a few pictures of me he ordered me to send him but this going to take it to another level.
On the big night I needed liquid courage and drank a couple of Martinis. Since I knew this was going to be a once in a lifetime experience I also set up my video camera behind and above the webcam so I could capture the entire evening on film and relive it whenever I had the urge.
I gave the performance a professional would have been proud of. My outfit was sexy, my make-up was perfect and with my wig you couldn’t tell I was a man – at least until the very end. I had music going in the background and stripped down to my garterbelt, stockings, lacy thong and matching lacy bra stuffed with my 40DD breast forms. I then pulled out an 8 inch realistic dildo and proceeded to give it head while looking into the cameras.
I licked it from tip to base to tip and then tried my hardest to deep throat it. Although I couldn’t take it all I was able to get most of it in my mouth. I was trying to show my Master how I would treat his cock if I ever had the opportunity. I then turned around and got on my hands and knees.
This wasn’t part of my planned striptease but the Martinis had loosened my inhibitions and I wanted my Master to get hard and horny watching me. I then reached behind me and pulled the thong to one side and proceeded to work the dildo up my ass. With only my saliva as lubricant it was difficult but I was horny and succeeded.
I fucked my ass silly then turned around so I was facing the cameras and pulled down my thong to show my Master how hard I was and to thank him for allowing me to perform. My Master rarely allows me to cum but I guess my show did the trick as he told me to stroke myself till I came while he watched.
It didn’t take much effort for me to cum then my Master signed off and I went to bed totally satisfied and exhausted.
The next morning I was awakened by my wife coming home early from her trip and opening the garage door. Fortunately, a neighbor was outside and she talked with her for fifteen minutes which gave me the opportunity to do a quick clean-up.
I quickly put the video camera away, hid my lingerie, put on shorts and a t-shirt, made sure I had no leftover make-up then went downstairs and greeted my wife. All was well and I escaped being caught by my wife crossdressing.
However, that same morning my boss called and told me she needed me on the east coast the next day for an emergency meeting. I quickly packed and caught a flight to Florida that afternoon.
This is where this story begins…
While I was on my trip to Florida my wife unbeknownst to me loaned the video camera to her very good friend Lucy so she could film one of nieces in a school play. Lucy used to work for me and we were once friends. But she now dislikes me from when I had to demote her. Lucy and my wife remain good friends while Lucy will not even talk to me.
A couple of weeks later Lucy invited my wife and I to a BBQ at her house. As there were going to be a houseful of friends and relatives I didn’t feel I would be obligated to make nice with Lucy and agreed to go.
The BBQ was good and it being a very hot day, I like everyone else drank too much beer. As things were winding down Lucy called us all inside the house to watch a couple of home videos. Almost all of us moaned but felt obligated to watch after enjoying the BBQ.
Lucy showed us her niece’s play and all the men complained. So she offered to show us a video of a stripper that she took at a recent party. All the guys including myself cheered and she pressed play.
Within 10 seconds I thought I was going to die of embarrassment. The stripper was me and it was the video I took when performing for my Master. How in the hell did she get a hold of it? I still didn’t know my wife had loaned Lucy our camera with the video I made still in it!
The guys were enjoying the show and I wanted to crawl away. Then I realized with my make-up and wig no one knew it was me and they even thought it was a woman. They went nuts when I sucked then fucked the dildo. Looking around I saw a few tents in the front of their pants and even a couple of guys were rubbing their hard-ons. Those sick individuals, didn’t they realize they were watching a man strip and suck and fuck the dildo?
I knew what was coming at the end of the video when I pulled down my thong and jerked-off for my Master and was waiting for the group’s reaction. It never came as the video ended before then and everyone thought I was still a woman and my identity was safe.
The guys wanted more details about the stripper and Lucy exclaimed “Her name is Cynthia and she claims she strips at parties to earn extra income but I suspect she does it because she’s a slut and an exhibitionist.” How did Lucy know my feminine name was Cynthia? Had my wife shared some of my secrets???
Mark, one of the single guys at the BBQ, announced he wanted to hire Cynthia to strip at a bachelor party he’d be throwing in a few weeks. Lucy with a big smile at me offers to set it up.
“Does Cynthia do more than strip?” asked Mark
“What do you mean?”
“Does she do more than strip and play with a dildo?”
“No I don’t know, you need to spell it out.”
“OK, S E X”
“I guess we could ask her right now” with an evil smile at me.
“What are you going to do, give her a call right now?
“No, I’ll just ask…” long pause with that evil grin “you to think about what you specifically might want like. Usually men want blowjobs and to fuck tight little asses – is that what you want me to ask Cynthia if she’ll do?”
“Hell yes, and how much?”
“OK, I’ll do it.” as Lucy smiled at me. “I know Cynthia charges a flat fee for an evening’s entertainment and will perform any and all sex acts. So if you hire her she will arrive at the specified time and not leave till everyone is totally satisfied.” “How do you know this?” asked Mark. “Because my husband once hired her for a bachelor party and I understand she didn’t leave until no guy could get it up anymore.” I wanted to run and hide! But what could I say or do? I just sat there looking at Lucy while she kept digging a deeper hole for me.
My only thought that kept me from running was that no one would ever see Cynthia again. I made up my mind right then and there that I would never dress up again. Cynthia would just disappear from the face of the earth. At least that’s what I thought till Mark asked Lucy if she really thought she could get Cynthia to perform for him and his friends?
Lucy said with a shit eatin grin “I can guarantee it!” And then it hit me, Lucy has the entire original tape where I filmed myself from start to finish transforming myself from a nude man with a hard-on to the woman everyone just saw doing the striptease and then sucking and fucking the dildo. She was the one that edited out the parts that would give away my identity. I knew then Lucy had me over a barrel and I’d be forced to do everything she ordered or she’d share my secret.
“So my recommendation is you invite as many friends as you can think of to your party and charge them a nominal fee to cover Cynthia’s fee. That way you and your friends can get all the sex you can handle for almost free.”
“Wow, that’s pretty sweet of you Lucy! We’ve known each other for years but have never been close friends. Why are you going to set this up? And not that I’m complaining just curious.”
“Let’s just say that at the bachelor party I was referring to, I suspected Cynthia had sex with my husband and I want some revenge.”
“What?” I wanted to scream but couldn’t. I never attended a bachelor party as Cynthia and definitely never had sex with her husband – I’ve never had any sex with any man!!!
“The price for me setting this up is I get to attend your party with a large strap-on and fuck Cynthia’s ass. Don’t worry I won’t stay too long and prevent you from having fun. I just want a little payback and I know you guys with all your lesbian fantasies would love to see me fuck her ass.” Lucy smiled at me when she said this and I knew then this had to do with me demoting her a couple of years ago and she was finally going to pay me back in spades. There’s nothing like a woman scorned!
OK, let me say at this point I was totally humiliated and embarrassed although no one but Lucy would have known or suspected what was going through my mind. But the worse part was I had an erection! How could that be?
Thinking back now I think for the first time someone was able to duplicate the humiliation my sister put me through when I was 10 and I was turned on. I knew then I’d do whatever Lucy ordered going forward no matter how embarrassing or humiliating to keep this “sexual feeling”. This doesn’t mean I’d ever let her know. In fact I was determined to say “no” every time she told me to do something and force her to order me to “do it or else.” The “or else” threat I knew she would be good for and she probably wanted to do anyway so I thought the more I said “No” and fought her orders the more she’d push my limits! Man, was I right!
The next day Lucy called me at work. How she got my number I don’t know since I recently changed employers and she never called me there before. When I answered the phone she sweetly asked for Cynthia. I pretended I didn’t know who Lucy was even though the caller ID gave it away and told her she must have the wrong number.
Unfazed she said “I don’t think so and I’m just calling to confirm my lunch date with Cynthia for tomorrow at noon at Scopazis restaurant.” I didn’t say a word. After about a minute of dead silence where you definitely hear a pin drop from a mile away Lucy said “Cynthia better be there or the entire tape, not the edited version, with about 50 copies will show up at work and also with your family and friends. Would you like that?”
Again I was speechless. What could I do? What could I say” “If Cynthia’s not at the restaurant at noon the tape will be distributed. It’s your choice.” I finally spoke and agreed to meet her for lunch but said I couldn’t dress as Cynthia at work and would therefore have to come dressed in my male clothes. She laughed then said “I agree so here’s what you’re going to do. You will call in sick tomorrow. You will dress as Cynthia and you will meet me at Mt Diablo state park at 11:00AM at the picnic grounds.” I now knew she’d already given this plenty of thought and I was being played by someone better than me at this. So much for me trying to control the situation.
The next day I woke up early without the need for my alarm clock. As you could expect, I was very nervous, had lost that “sexual feeling” and tried for the umpteen time to think of a way out of meeting Lucy but couldn’t. I called in sick with the flu – a lot’s been going around so no one at work would think anything of it.
I finally gave in to the inevitable and got in the shower and shaved my entire body extra close including my cock and balls but left a little landing strip just like a woman would do. I even shaved my face twice but left the hair on my head. After drying off I rubbed some of my wife’s body lotion all over. My cock immediately got rock hard and I wondered whether if it was the lotion or was it because I finally had someone forcing me to dress as a woman and do who knows what and I wouldn’t have a choice! I was totally humiliated and turned-on at the same time. I wanted to stroke myself and knew it wouldn’t take much to make me cum. But I knew if I did I’d lose the horny feeling and anything Lucy made me do would be that much more difficult mentally to do so I didn’t.
Then I dressed as “Cynthia” but not knowing what Lucy expected and being the middle of the day in a state park I decided to dress casual and for outdoors. I put on beige thigh-high stockings, a lacy white thong that had enough material to keep my cock and balls tucked back between my legs but showed off my landing strip. I put on a lacy white racer-back bra stuffed with my 40DD breast forms and a white racer-back t-shirt, a blue jean mini-skirt and women’s white with pink accent tennis shoes. The outfit wasn’t overly feminine but would never be mistaken for men’s clothing.
I then took the time to make sure my make-up was perfect as I knew in a couple of hours I was going to have to try to pass for a woman. My pink lipstick matched my pink eye shadow which was the same shade of pink as my long fake fingernails I had glued on. My wig was a deep auburn color that came just to my shoulders and had a lot of loose curls. To finish off my outfit I put on a gold necklace, dangling clip on earrings (my ears aren’t pierced) and a women’s ring on each hand. It might not have been needed but not knowing what Lucy expected, I sprayed on some of my wife’s Obsession perfume. I had no place for my wallet so I grabbed a small pink purse I bought one time on a whim and because it was on sale. I put my driver’s license, a credit card, the $8.00 dollars in cash I had and my cell phone into my purse and at 10:30 got into my car in the garage, opened the garage door and drove off to the state park. I prayed none of the neighbors saw me as I never go out during the day as “Cynthia” and would die of embarrassment if I was caught by someone I knew and would see everyday going forward.
The drive to the park was nerve racking but also a turn-on. The only way to the park was to drive the entire way on 4 lane roads with lots of stoplights. Every time I came to a stop I didn’t want anyone stopping next to me and looking over and seeing I was a man dressed as a woman. On the other hand, every time I stopped for a red light I wanted a truck to pull up along side me and have the driver check out my stocking covered legs, my miniskirt and my 40DD breasts with nipples that clearly showed. My little head started thinking for my big head and the fantasies started coming and I got as hard as my tucked cock could.
My fantasies and hard-on came crashing down when I had to stop and pay the entrance fee at the park’s gate. The ranger looked hard at me and I knew he knew I was a man dressed as a woman. I paid the $5.00 entrance fee and didn’t say a word as my voice would have confirmed I was a man.
As I was about to drive off he smiled and said “Lucy wanted me to tell you she has moved your lunch from the picnic grounds to campsite #13 and you’re to meet her there. I’ll see you later.”
Uh oh! I now knew I was in deeper trouble than I could ever have imagined. I thought all Lucy would have me do was get out of the car and force me to walk around the picnic area all dressed up as a woman so I’d be seen by other picnickers to humiliate me. I never guessed she would involve someone else, much less a ranger!
I looked at the map the Ranger had given me and drove to campsite #13. Not that I’m superstitious, but in the back of my mind I hoped it wasn’t an unlucky #13.
When I arrived I found Lucy already there. She was sitting at the campsite’s picnic table with an evil grin and indicated I was to get out of my car and walk over to her. I hesitated as long as I dared then slowly got out of the car and walked over to her.
Other than my wife this was the first time anyone I knew was seeing me dressed as a woman. I was totally humiliated and it would have been bad enough if it was a friend or neighbor that caught me by accident. But this was a woman that had a grudge against me and I had no option but to do anything she wanted.
When I finally stood in front of her she smiled and told me to turn around slowly in a circle so she could see all of me. When I was back facing her she smiled her evil grin again and said “I’m glad to see you can follow orders Cynthia because that’s what you’re going to be doing all afternoon and then anytime in the future I choose to give them. Do you understand?”
“Not entirely. I know you have a tape of me dressed and doing things I’d rather not let anyone see, but I’m assuming you’ve ordered me here today to embarrass and humiliate me for some revenge you perceive you need to get. I’m reluctantly complying with your demands today and will do anything you order me to do to satisfy your need to humiliate me. But then it’s over and I want my tape back and we never need to speak to each other again.”
I was being eloquent, logical but delusional and Lucy saw it different. “You demoted me two years ago and I’ve had to face my family, friends and business acquaintances everyday since then with embarrassment and now you’re going to pay. However, you’re not worth two years of my time so here’s the deal. I’m going to condense your humiliation into two days. You will do anything and everything I want today and then again one night in the near future. Then I’ll give you back your tape and all the copies I’ve made. Do you agree or should I distribute the copies I made of your tape tomorrow?”
“How do I know you’ll keep up your end of the bargain if I do whatever you say?”
“You won’t know for sure, but in all the years I worked for you or we’ve known each other, have you ever known me to lie?”
“No, you’ve never lied that I’ve known about, so I guess I have no option but to trust you. So do your worst and let’s get this over with. No, no, no, I’m just kidding; please, please do not do your worst!” Damn I hate it when my turned on cock makes me say things that will get me into trouble!
After a few seconds and coming to my senses. “On second thought, you must promise me you won’t make me do anything to get me arrested or I’ll get back in my car right now and drive away and the hell with what you’ll do with the tape!” Pretty strong words for a man with no legs to stand on – but I had to try.
“I swear, I’ll not order you to do anything that will get you arrested.” Then with her evil grin. “After all, if I want to see you butt fucked, I want to see it up close and personal. I won’t get to watch if you’re in jail. So no, I swear I will not get you arrested.”
Lucy gave me another evil smile and at that point I should have known she had already thought through this entire scenario and was a hell of a lot smarter than me. I was doomed and didn’t even know it!
Lucy then pulled out a pair of handcuffs and handed them to me and told me to handcuff my hands behind my back. I didn’t see where I had a choice so I did as ordered. She then told me to sit down and said “Let’s talk. I’m going to ask you some questions but before I do, you need to know I expect your answers to all my questions to be immediate, truthful and complete. If I catch you in a lie or even suspect you’re lying, then the tapes will be distributed. Do you understand?”
“Do you believe I’m still pissed at you enough that I’ll distribute the tape if you don’t answer my questions truthfully or don’t do anything I say both today and next time?”
“That’s good you believe it because I swear I will. In fact I’m still so pissed at you I almost hope I catch you in a lie or refuse to do something so I can distribute it. So let’s begin, why did you make that tape?”
I hesitated for a few seconds but knew I had no choice but to answer so I said “My online Master ordered me to do a strip, suck and fuck performance for him via my webcam and I decided I wanted a video to relive what I did at a later date.”
Lucy burst out laughing “You have an online Master, why? Does he know made this tape? I want his e-mail address.”
The questions kept coming and I answered each one truthfully.
Then with her evil smile Lucy said “Let’s change topics. Have you ever had sex with a man?”
“Dressed like you are and after watching your video I don’t believe you. Tomorrow I’m going to distribute your tape.”
“No! I’m being honest I’ve never had sex with a man. I’ve had fantasies, but have never, ever, ever had sex with a man! You’ve got to believe me!” I cried.
“OK, then tell me your gay fantasies and if my pussy isn’t dripping wet when you’re done, then I’m distributing the tape.”
I had no idea what would turn Lucy on so I told her my most risqué fantasies as well as a couple of other kinky ideas that weren’t anything I’d ever fantasized about but hoped they’d get her off.
It must have worked because she finally smiled and said “I must admit those fantasies were hot and I’m going to do my best to fulfill each and every one of them.” Not what I had in mind when I started talking. “However, you never talked about yourself cumming, why not? I hate to give you a compliment but your hard-on at the beginning of the tape was very impressive and under different circumstances I’d jump your bone and fuck myself silly.”
I couldn’t believe Lucy was saying this. If I wasn’t married, I’d fuck her in a New York second. She’s a strawberry blonde with small tits but I’ve always suspected hot in bed! But I answered truthfully while leaving her out of the equation. “In my fantasies I’m always the submissive slut that’s not allowed to cum but must satisfy everyone else.”
“So slut, do you want to fuck me?
I had no option but to answer truthfully, “Yes Lucy, I want to fuck you.”
“Do you want to eat me?” Lucy asked while taking a very wet finger out of her jeans that could only have come from her pussy.
“Well here, lick my finger clean so you know good I taste.” She held out her finger and I tentively stuck out my tongue so I could lick it. “That won’t do! I want you to lick and suck my finger like it’s a hard cock covered in my pussy juice.” And with that she stuck her finger my mouth and held it there while I licked and sucked on it for at least three minutes.
“So how did that taste?” And I truthfully answered that it was very tasty. “Well maybe with a little luck today I’ll find a nice cock to fuck then allow you to lick it clean. I imagine it will be very wet from the tip to the base with a mixture of my pussy juice and his cum. And when you’re done licking his cock clean I’ll have him stick it back in my pussy to get it covered with our juices again so you can lick it clean a second time. You want to lick a cum covered cock for me don’t you slut?”‘
“No, I don’t. That would be disgusting!”
Lucy gave me her evil smile again and said “I’m glad to hear that because guess what? Today is all about humiliating you and now that I know it disgusts you, I’m definitely going to find a nice big cock to fuck then you are going to lick it clean! In fact I may fuck several cocks today and then have you clean them all. After all, just because you’re being humiliated doesn’t mean I can’t have fun.”
“Enough talking, let’s play” was the next thing Lucy said then she told me to stand up and turn so my back was to her. Lucy put a blindfold on me then told me to open my mouth. When I did she put what felt like a penis gag in my mouth and buckled it tightly behind my head. With my hands cuffed behind my back there was no way I could remove either one.
Next Lucy walked around to be in front of me and slowly unhooked and removed my jean skirt and helped me step out of it. She told me not to go anywhere and walked off I assumed with my skirt leaving me in standing in a white lacy thong and tight t-shirt that showed off my 40DD breasts beautifully. With the blindfold I couldn’t see anywhere to go so I stood there. Fortunately my car was blocking anyone’s view that happened to walk by. Lucy returned and shocked the hell out of me by reaching down between my legs and started rubbing my cock. It immediately sprang to life but was still tucked back between my legs and was limited in how big it could get.
Right then a car pulled up into our campsite and Lucy whispered “Right on time.” I couldn’t see to run. I couldn’t say anything with the gag in my mouth so I stood there. I heard two doors open and close and the sound of approaching footsteps. I wanted to die! I had no idea who they were or why but was totally humiliated standing there.
The footsteps came right up in front of me and stopped but no one said anything. I was going nuts!
Finally Lucy spoke but was having a hard time because she kept giggling “This is going to be so much fun Cynthia. I just know you’re going to have the time of your life!!! Standing in front of you are two men. In a few minutes I’m going to remove your gag and you’re going to suck each of their cocks until you can tell them apart and then you may name one Lord and the other Master. For the rest of the day you will call them by their correct name or there will be hell to pay. So you better take your time sucking their cocks to know which one is Lord and which is Master. You will be given a test!”
“Lord and Master have graciously agreed to pop both your cherries today and one will cum in your ass and the other in your mouth. Aren’t you excited?” Lucy continued to rub my cock and it would not get soft no matter how disgusted I was with what was about to happen.
“Just so you know why I blindfolded you. It’s because you know the men standing front of you and they know you, but I want you to always wonder which of all the men you know and see all the time they are. They might be family, friends, neighbors or co-workers but you’ll never know who they are. So from now on whenever a man smiles at you or tells you a gay joke you’ll turn beet red wondering if it was the man you sucked off or who fucked you in the ass. See, I like to give the gifts that keep on giving, humiliation for life!” Lucy burst out laughing.
I knew my face was beet red with embarrassment and humiliation but dressed as I was with my hands cuffed behind my back, a penis gag in my mouth and blindfolded there wasn’t a thing I could say or do. Lucy had me where she wanted me and I knew I was screwed – both figuratively and soon to screwed literally.
Lucy asked me if I agreed to suck and fuck or did I want the three of them to drive off leaving me as I was and they’d distribute the tape. I had no option and shook my head yes. Lucy ordered me to get on my knees and I heard two zippers being pulled down. She went behind me and unbuckled the penis gag and took it out of my mouth. I worked my sore jaw up and down a few times then Lucy said “Let’s find out who is Lord and who is Master”
To the two men she said “I know you’re both eager to have this hot slut get you off but please take your time and let Cynthia enjoy getting to know your cocks. She’s yours for the rest of the day so no rush.” And to me “Cynthia, take each cock as they are offered to you and make love to it with your tongue. I want to see you lick from the tip to the base then take their balls in your mouth one by one and suck gently.”
As the first cock touched my lips I wanted to refuse but had no option. I opened my mouth and was fed an enormous cock that was still only half hard. I licked the tip and tasted some pre-cum. Oh my God! It’s one thing to taste your own but another man’s? I don’t think so, but again I had no choice so I continued to lick and then suck this cock. I felt it hardening and when fully erect it didn’t come close to fitting in my mouth it was so long. I was forced to pull my mouth off it then give it a tongue bath. When I got to the base of this long cock I continued on down until I was licking his balls. I was surprised to find them shaved and it actually wasn’t too bad sucking on them one at a time. After I sucked both balls I licked my way back up to the head then took in my mouth as far as was comfortable and gave it a good sucking. I was rewarded (if you can call it that) by a lot more pre-cum and this time it didn’t taste too bad! I swear his cock was 12 inches long – or at least it felt that way.
His cock was pulled from my mouth and within a few seconds another was pushing against my lips. I opened my mouth and the thickest cock you can imagine shoved its way past my lips. Fuck it was thick and I swear it tasted like Lucy’s pussy juice. I wondered if he was fucking her while I sucked the first cock. I licked the head and sucked it as far as I could get it in my mouth which licked my way down to his balls. It must have been my lucky day since his balls were shaved also. I took my time and licked and sucked each one then worked my way back up to his tip where I sucked the head again enjoying his pre-cum.
He eventually pulled his cock from my mouth and Lucy asked “Well slut, which cock is your Master and which cock is your Lord?” Finally a question that wasn’t hard to answer. “The first cock is Lord and the second is Master.” I said. What I didn’t say was how I named them. The first one was so fucking long it had to be Lord because of the first letter “L”. And the other was Master because it was such a monster – the letter “M”.
Lucy said “fine” (which I’ve always heard means you’re fucked) and now I was about to find out it was true. Lucy told me I couldn’t be fucked wearing a thong so she was going to remove it. She pulled my thong off and pulled my cock out from between my legs and rubbed it some more. It was probably the hardest it have ever been in its life and I had to ask myself was it the humiliation I was getting off on or was I looking forward to my first gay experience?
“OK slut now it’s time for your test. You get to suck on one ball of your Lord and one ball of your Master for 10 seconds each. If you can tell me who is who you get to choose which one fucks your ass. If you can’t, then I choose and you get some additional punishments.”
How could she do this? I could tell by cock head size but didn’t pay much attention to their balls. They were both shaved and very large – nothing else stood out!!! I took the first ball offered me and licked and sucked it then did the same with the second. There was no difference, I couldn’t tell them apart! Lucy asked which ball belonged to whom and ordered me not to guess. I had agreed earlier to be truthful and therefore told her I couldn’t tell.
She started laughing and said “Perfect, I’ll choose which cock fucks you and you’re going to beg for it! Aren’t you slut?”
“Yes Mistress.” Now why would I ever call Lucy “Mistress”? This whole scene was beginning to freak me out.
“But before we begin we need to do a couple of things.” There was some moving around and noises I couldn’t identify. Something was placed in front of me and I was told to spread my legs and bend over it. It felt like a padded bar about waist high. As soon as my legs were spread there was something attached to my ankles and in turn attached to whatever I was bent over. Now I was truly helpless. I was bent over with my bare ass exposed and my legs restrained very far apart. With my hands still cuffed behind my back there wasn’t a thing I could do to prevent them from doing anything and everything they chose. Talk about feeling vulnerable!
“OK slut, I want hear you beg to suck Lord.” I had no option so I humiliated myself further by saying “Lord you’re such a huge cock, you’re so long, I want to suck you, I want to deep throat you, I want you to cum in my mouth, I need you in my mouth, oh please let me suck you, I’ll give you the best cock sucking you’ve ever had. Please, please, please let me suck you!!!” And with that Lord entered my mouth.
I licked, sucked and took as much as I could which I’m sure wasn’t even half his cock. I was rewarded with more pre-cum and was determined to get him to cum as quickly as possible while also giving him the best head he’d ever had. After all, if you’re going to do a job, you might as well do it right.
I was just getting into a rhythm when Lord was pulled from my mouth and replaced by Master. I made the same great effort to get Master off when Master pulled out.
Lucy said “I hope you got Master nice and lubricated because that’s who’s going to pop your cherry when he fucks your ass. Now, we want to hear you beg for Master to fuck your ass.”
I couldn’t do it. First I’d never been fucked in the ass before. Sure I’d used a few dildos over the years but they were small. Master was unbelievably thick! There was no way I could take that monster up my ass. I knew if that cock made it into my ass I’d be ripped apart and would bleed to death (OK, bleeding to death was an exaggeration). But I knew my asshole couldn’t stretch that big so I didn’t say a word.
“We’re not hearing you beg slut. Are you worried Master might hurt your virgin ass?”
“Well perhaps you need some incentive to beg?” I heard a swoosh then my ass was on fire! Lucy had whipped me. Then my ass was whipped five more times. It hurt like hell and I wanted to scream out but didn’t. Lucy chuckled and said “You know how pissed I am at you, but you don’t know how much I’m enjoying this. I’m going to keep whipping your ass till you beg for Master to fuck it. And you eventually will because I will not stop till you do. So please, don’t beg for a long, long time and let me have fun whipping you!”
Whack, whack, whack… I couldn’t take the pain anymore so I cried out for Lucy to stop and allow me to beg for Master to fuck me. She whipped me a few more times while laughing and telling me how good it felt and didn’t I enjoy it also. No, I didn’t, but now I had no choice but to beg for Master up my ass.
“Master, I’ve never imagined a cock of your size existed. I would be honored if you’d take my cherry by fucking my ass. Please say you’ll do it! I need my ass fucked so bad. And it’s so hot for you. I don’t want a smaller cock, I need you now! Please fuck me as hard as you can. I know it will hurt because you are so big but please don’t show my ass any mercy! I’m begging you, shove Master up my ass now and fuck me for all you’re worth.” I practically screamed the last part and was rewarded by Master pushing at my back door.
I could tell he lubricated that monster because the head was starting to slip in without much effort but the more he fed my ass the more it hurt. I swear I my asshole was being ripped apart. It was reaching the point of pain Lucy gave me by whipping my ass and he was barely in me. My God! What would it feel like when Master was all the way in? The only consolation going through my head was how I always read how an ass fucking hurt at first but as they went on how good they felt. I couldn’t imagine that now with how much my ass hurt as he shoved a few more inches into me.
Another few inches were shoved up my ass and I opened my mouth to scream in pain but was quickly gagged by Lord shoving his hard cock in my mouth. I heard Lucy giggle and say “Remember no teeth!” Lord tasted like Lucy’s pussy and I wondered if he’d been fucking her while Master was working his way up my ass?
OK here I was, tied bent over dressed from the waist up like a woman and giving my first blowjob while being fucked in the ass while a woman that hates me was watching. Could it get any worse? Yes, it could as I was to find out.
I sucked Lord with all my new found skills of cock sucking for all of one day. I wanted Lord to cum as quick as possible to get it over with. But Lucy had other ideas and told Lord not to cum in my mouth till after Master came in my ass.
Lord pulled his cock out of my mouth which allowed me to concentrate on Master up my ass. Master was no longer being nice and gentle. I was being fucked ferociously and I hate to admit it, loving it. Master was pulling almost entirely out of my ass then shoving in as hard and deep as possible till I felt balls slapping on my ass.
Perhaps he was rubbing my prostate, I don’t know. But I was so fucking turned on and had one hell of a hard-on which Lucy pointed out!
Master’s pace finally changed and I felt him deeper than ever and then I felt him cumming in my ass. I couldn’t prevent it and opened my mouth to sigh and was rewarded with Lord in my mouth. Again it tasted like Lucy’s pussy and I was glad. Because if he’d been fucking her then he was that much closer to cumming!
I was either right or a very good cock sucker because Lord didn’t last more a few minutes but I swear he pumped a quart of cum into my mouth. I swallowed what I could but some did escape and drip down my chin. I couldn’t believe everything that just happened but what was worse was I still had the erection of a lifetime!
I stayed there bent over the bar trying to recover from the onslaught when I heard footsteps going away then car doors opening and closing and a car drive off.
“Now for the rest of the story.” Spoke Lucy “I grew up listening to Paul Harvey and have always wanted to say that. If you couldn’t guess, it’s just the two of us now as Lord and Master have left. You’ll never know who they are but I guarantee you will see them all the time going forward. How embarrassed and humiliated will you be everyday knowing you begged to suck one of their cocks and took the other one up your ass?”
“I’m going to be leaving soon myself but there are things you should know. But before I tell you I think you need to be gagged again. The penis dildo I’m going to gag you with has been in my pussy soaking up all my pussy juice while you were being fucked. I hope you enjoy the taste of the most perfect pussy you’ll never see or get to fuck.” And with that, Lucy gagged me with the penis dildo with her juices all over it. Lucy’s pussy juice did taste great and it helped get rid of Lord’s cum taste that was still in my mouth.