Amanda's Fantasies Amanda and the landlord
By Amanda S tv_amanda_s@hotmail.com
"Oh come on Ben, give us a little more time". Ben our landlord owns the building where my wife and live. He had three floor through apartments, big ones. Ben lived on the first floor, the second was empty and my wife Jenny and I live on the third. Ben also owned the restaurant below the apartments. Our apartment was very spacious, Jenny had decorated it beautifully and we were about to be evicted.
"Look guys, I know your money situation sucks but you're six months behind. I've Been renting to you way below market price. I hate to do this but you have a week to either come up with the money or leave.$18,000 or you're out and I'll have a city marshal grab your belongings and sell them. And I want you also to remember you cost me big with that bad investment advice – over $250,000 so why should I give you any more breaks?" Jenny began to cry, Ben down looked at us. He 6 feet tall as opposed to my 5'8'.He was an athlete in college so he is muscular without looking like a freak. Jenny says he's hot; I'll take her word for it. At one point We were loaded; I had a great job and met Jenny there. We were able to afford this apartment and live the good life traveling and fucking like rabbits. Then one bad investment cost my company millions of dollars. I got fired, Jenny got fired and our investments got wiped out. The only income we had was from Jenny working as a hostess in Ben's restaurant. And now we were screwed.
Jenny began to cry. She asked if there was any way they could pay it off in other ways. Anything. She stopped for a second and then said "I'll even blow you." "Whoa" I said."We never discussed this. You are not going to blow him, no way".
Ben didn't say a word, He just looked at us and said" You know that doesn't sound like a bad idea. The thing is, I don't want you to blow me Jenny"-he pointed at me" I want him to blow me. Not only that, I want you dressed up like a girl, I want "her "to look sexy and like a real girl, not a slapped together guy in a dress. I'll even pay for any supplies or clothes you need, but I want sexy from top to bottom. The lingerie should be as sexy as possible. Does that seem fair? Between the rent and the money it seems very fair." "Are you out of fucking mind" I said. "There is no way, no how, I am going to ..." I go cut off by Jenny. She said "We'll think about it". What the fuck do you mean "we'll think about it? Are you fucking...?" Ben cut me off. "Look, it seems the two of you have a lot to discuss but if you don't give a blow job on Wednesday you have to leave Thursday" and left.
I was fuming at Jenny." Are you out of your mind, He has us where he wants and so he makes an outrageous deal and you say we'll think about it. Have you gone crazy"? Jenny just looked at me, finally she spoke. ". I love you but you got us in a terrible bind. "This guy is offering us a way out so yeah. We have to think about it. We have nothing because of YOU. YOU have to get us out of this mess, YOU lost us over a million dollars, YOU fucked up and got fired and because I was married to you they fired me too, You'll never get another job at a bank or brokerage firm again and if it means dressing up like a woman and giving a guy a blow job then that is what you are doing or I am walking". I took a swig of scotch that I poured. DO it or I am gone. I will help make this as easy as possible for you and believe me giving a blow job is not as bad as it seems. I have sucked more cocks than you know before you". My face turned white. "It's not that hard. Dressing you up like a sexy woman will be the hardest part". She pushed me on the bed pulled my pants down and began sucking my cock. She moved her hand up and down as she sucked, Still moving her hand up and down she stopped sucking, ran her tongue around my shaft and began licking my balls. God, I loved that. She took my cock back in her mouth and I suddenly felt a rush as I came in her mouth, she was still sucking and pumping as I came until every drop came out. She took my cock and she licked every drop off my shaft. She swallowed it all up and looked me in the eyes and said "Is that really that hard to do? You're going to do it and we are free".
Jesus H. Christ. The thought of doing this was making me sick but there was something about the way she said it that made me think that I could do this and not get sick. "Okay, where do we start?" She looked me over."The first thing is you need to shave, your face, and your legs and under the arms. You don't have a lot of hair on your chest so that will be easy." She led me into the bathroom, I was already half naked from when she blew me so I took off my shirt. She handed me a pink razor. "It's designed for women but I don't want you to hurt yourself so I'll do it the first time. She shaved my legs and armpits and showed me how to do it so I don't cut myself. I shaved off the small amount of hair on my chest." She began dressing me; put her bra on me and a pair of panties. It was tight, Jenny had a nice set of boobs but she was small so it looked like I was wearing a tight bra with no boobs. She looked me over. "That is not going to do it, you're going to stretch and probably break the snaps and my panties are way too small for you. She pulled out a credit card. "Ben gave this to me to buy you clothes so we are going shopping". I thought for a second. "Can't you do this yourself? I mean, you figure out my size and then buy it...." "That won't work. We have to get your dress size and make sure all the lingerie fits right," "I am not shopping like this". "Of course you're not. I have to work with what I have makeup, a wig, a dress and pantyhose to hold your dick back. Trust me; no one will know you are a man. Now watch as I show you how to use makeup."
She took me through the whole regiment, blush, eye makeup, lipstick. Jesus, she does this every day. I listened as she applied the makeup on me. She looked at me and said" did you get all of that". Surprisingly I said yes. She said let's get a wig before you look. How would you like to be redhead? Oh Christ, I actually said I would and she fitted the wig on me. Jenny said I could look now.
I looked in the mirror.Damn, I make a good looking woman. (Holy shit, did I really think that?). Jenny looked at me and said, "Hmmm, much better than I would have guessed. Now I have to figure out...Okay, I have this old bra which I don't care if it gets stretched". She got out a pink bra and fastened it on. She closed it , it felt tight but at least I would buy lingerie that fit me (Did I really think that?). right.She took a couple of pantyhose, rounded them out and stuffed my bra (My bra?). She spent a few minutes trying to get it look right. She then had me put on a pair of her panties and pantyhose. "You had to pick pink, as if this isn't embarrassing already". She looked at me and said "You look great, no one would guess. Look at yourself". She had done a great job, you would have to look close to guess I was a man. She looked at me and smiled. "Time to go shopping honey". I groaned.
We got in the car, Jenny said," I googled this place, it's perfect." We pulled up to a lingerie shop called "Special Women". We went in and walked up to the counter. A woman with huge tits turned around and asked if she could help us. There was something about her that didn't sit quite right. Holy Shit – I think that girl is a guy. She had dragged me to a transvestite shop! A voice behind us said, "I have this one Danielle". I turned and this incredibly hot woman was standing there, about 5'6" tits bigger than Jenny's. One look at her and I knew she was real deal.
Hi, I'm Jessica and yes I am a real woman. "She looked at me and said" You can stop looking at my tits, they are real." Jenny gave me a poke." I always take care of the first timers and I can tell you are. Nothing fits right and the boob job is not the best. Are you ready to go all out?" Jenny waved Ben's credit card and said "lets to it and do it right". I was so distracted by what was going on I didn't even think about what we were doing, the next thing I knew I was trying on garter belts with the girls showing me how to attach the stockings. I learned what a merry widow was and tried on different bras, panties in different colors;we seem to be buying a lot more than I thought I would need.
She came our next with a pink bra and panty set with thigh high pink fishnet stockings. I said" I think we can draw the line about pink." Jenny said I'll buy them and then you can decide whether to wear them or not After buying what about everything "These are the best she said. They are flesh colored. They even have nipples "so if you are wearing something shear it looks real, you'll even have a cleavage in the right top. She also took out a red bra and a red garter belt; "this is very comfortable. you don't feel tied in. Now let's not forget the shoes, it's not like you can walk into 9 West and find your size, I tried on three pairs a flat, one with a heel and one with a very high heel. I nearly fell over in those and Jessica said that those shoes take a bit of getting used to hrough so I should stick with the open toe with the got small heels for now. She looked down and said we if I was wearing an open toe I needed a mani pedi Jenny said" As soon as we get you done we'll go the salon." `"Oh come on this thing has already gotten out of hand.", " Jessica walked up to us." Look I don't know what's up and it isn't my business. I let my customers have a place to go to, no questions asked. If the nails are an issue I have an agreement with the salon down the block. They don't ask questions either and I refer customers to them. Danielle goes there twice a week. They know what she's transgender and don't mind at all." Jessica adjusted my bra and pantyhose, picked out a couple of skirts and tops for me to try on. "I put on a black skirt with a gray sweater. "Oh, you look so pretty" Jenny said. I pulled her aside.
"You seem to be enjoying this a little too much" I said to her.
"Well, maybe I am, I don't know why but I am enjoying it and if you would relax you will enjoy it too. "After settling on a few skirts and tops we gathered up all the bags. Jenny looked at the bill and her eyes widened. "Shit for this amount you are really going to have to take care of him." I groaned as we walked to the nail salon.
We headed home after the nail salon. We kept the colors light so I wouldn't stand out when I was out as man. She looked me over and said "This is why I am so in love with you. You are trying to protect us and you're right this may be a little more than we expected, hopefully he'll stop after one time, sort of a `look what I can make you do" type of shit. I am going to give you the fuck of your life and a blow job that we keep a smile on your face so big that the blow job you are going to give him will seem like nothing. Now lift that skirt and let's fuck. "
I started to strip when she said "Just take the pantyhose off and lift your dress, we are going to have some fun with this."
Wednesday came. I was supposed to be at his apartment at 7 PM. About 5PM Jenny began working on me, the shaving, the makeup, picking out the right lingerie (black long line bra, garter belt and fishnet stockings). Skirt that just covered my knees, and silk sweater. Just before seven Jenny hugged me and said" I am sorry you have to do this, I love you " and I got on the elevator, The elevator ran through all three floors with a small vestibule and a door when you get off. I got off the elevator and found the door to Ben's open. I entered and he was on the couch. "I was wondering if you would really do this" he said. Turn around and let me look" I turned around and faced him. "Jenny did a great job on you. I just checked my credit card; I see the two of you went to town. I expect a return on my investment this time. Come over here and take the skirt and blouse off." I took it off so I was standing there in my lingerie."Body needs a little work but still not bad. Now get on your knees." I got on my knees."Pull my pants off ". I did and he didn't have anything underneath. I was face to face with his rather large cock. I am not a piker in that area, but he was huge. "Now, give me a blow job Amanda". I was confused."That's your girl name", I was shocked. He had picked out a name? I took a little offense and he saw it. "Oh you don't like your name huh. Okay before you blow me I want to you to say I am Amanda your sissy cock slut". I hesitated, he said "Say it godamn it or the deal is off!" I did and then he told me to blow him an and said I was Amanda your sissy cock slut.I looked at the cock and how Jenny said it was easy. I opened my mouth and next thing his cock was in my mouth.He also told me if I did a good job it would be over quickly so I began sucking. I did to him everything Jenny did to me and in almost no time I felt him stiffen up and began cumming. I began to pull away but he grabbed my head and said "Take it all bitch, swallow it and don't stop until "I'm done"..His cum shot into my mouth and down my throat, I began gagging but he wouldn'tried to pull away. He looked at me and said" Damn you are good. See you in a couple of days my little cock whore." I almost cried and ran out the door up to our apartment.When she saw me Jenny began crying and held me, "I didn't think he would force you to do this."
Tne rang and she answered. She spoke in the phone."No you fucking son of a bitch. So kick us out, I don't care anymore. I have Adam, what do you mean Amanda? No that was not part of the agreement. You can't change it. Fuck you. What you bastard. You won't do that. ".She slammed the phone down and said godamn him. I looked at her. He says he has a nice video of it that he'll post for the world to see if we don't change the agreement. I looked at her and she continued. "The blow job is now daily, I won't..."" I cut her off. " It's the only way,Call him back and tell him I'll do it."
For the next few weeks I sucked him daily and surprisingly after the first time I didn't mind it,I got a a pep talk from Jenny every time I started to actually enjoy it. I enjoyed dressing up and then blowing him. Who would have thought? He began asking me to tell him how much I enjoyed give him a blow job and how I was his little sissy cock whore. I repeated it back willingly.
One day I came down in my black merry widow with lace panties and he said we're going to amend the agreement. I began sucking him. When he was really hard he told me to stop , pull my panties off (which he never asked me to do ) and how he was going to fuck me in the ass, how it wouldn't hurt and how I would come when he did because I liked it so much. He fucked my ass and I squealed as he moved in and out. God this feels great. He was right, as soon as he shot his load in my ass I came.
My sex life with jenny was still great; I became Amanda full time so I guess it was a good idea to having bought all these clothes. Jessica dropped by one day and said she had some hormones if I wanted them. I looked at Jenny; she was nodding her head so I started taking them. When Jenny found out Ben was fucking me she said she wanted in and bought a strap on to fuck me with.
One day he didn't make our daily appointment because he was helping someone move into the second floor. I didn't mind if the people saw me, none of it mattered any more, I enjoyed what I was doing. The following day I came down to his apartment wearing my pink bra and panties and pink thigh highs and high heels. I started blowing him when I heard the door open. Standing there was Jenny, Jessica and Danielle all naked. Jenny and Jessica started feeling each other up and broke out laughing. I stood there stunned.
Jenny said "you're probably wondering what is going on. We have been planning this for months. I've had a threesome going with Ben and Jessica and occasionally Danielle you thought I was working After for a while. We decided to transform you into a woman You don't know it but I started drugging with this interesting drug which makes you listen to what I say . If I say we are going to dress up as a woman and if I said you're going to enjoy sucking his cock you end up doing so. Why? It turns out Ben actually invested a against you and is very, very wealthy on top of what he already had. We decided we wanted to turn this place into our own sexual playground. We have two women (she and Jessica kissed), two she males and Ben. The combinations are amazing! If you want to fuck Jessica go ahead. If you want to fuck Danielle or have Danielle fuck you, you got it. If you want we'll get you real tits like Danielle. Ben gets all four of us and we all get the other four. It is going to be amazing." She paused. "You know what's kind of amazing? I stopped giving you the drug a few weeks ago and there you are blowing and getting fucked by Ben even without the drugs.
I answered her by taking Ben's cocking in my mouth, sucking him until he blasted his cum in my mouth and on my face. licked the cum on my lips, I l looked at Jenny and said "I know".
I hope you enjoyed one of my fantasies. You can let me know at tv_amanda_s@hotmail.com
Xxxooo Amanda