The Man From Sear's Mensroom

I opened my email a couple days ago and there was a message from the gentleman I met in Sear's mensroom. I became very excited as I read it, "my wife will be out of town for a week visiting our daughter in Utah, I would love to get with you. I will be waiting to hear from you".
I don't normally suck the same cock twice, but my mind went back to the day I met him, remembering the copious load he fed me and the way he talked to me, I decided I needed to suck his cock again.
My email read "I would love to get with you again, let me know when you will be available.
His return email contained his address, date and time, it also asked me to be discreet. Discretion is always a priority for me so there would be no problem.
I pulled into his driveway, his house was large, very nice and well kept, the neighborhood very upper class. He answered the door dressed in a knit shirt and slacks, "hello, come in" he said. His home was beautiful, you could see the woman's touch. "I'm so embarrassed, but I don't even know your name" I said as he led me to the f****y room. "It's Conrad, and yours is" he answered, "Richard" I replied. "Can I make you a drink?" he asked. "Rum and Coke" I said. As he made our drinks he said "I have a present for you and special request, down the hall, the second door on the left". I went down the hall, it was obviously the guest bedroom, on the bed was a large box from Kohls, opening the box there was a note on top of the tissue paper, "I hope these please you, as they will most certainly please me, please, feel free to make yourself at home and take all the time you need ,I've also left some things in the bathroom." it read. I folded back the tissue paper revealing a beautiful pink bra with small inserts, panties, garter belt and nylons and a pair of shiny black heels. I've had encounters over the years with men that wanted me in girls clothes and I have occasionally obliged, they have all had the same motive, I knew what Conrad had in mind. I'm not gay, I don't fuck, but I'm not a virgin, (that's another story). I decided to see what other surprises he had for me in the bathroom. There was a beautiful silky short black baby doll dress hanging on the shower rod, on the vanity was a cute shoulder length brunette wig on a Styrofoam head, makeup, nail polish and a disposable douche. I was overwhelmed with the amount of time,effort and money Conrad had invested in trying to make me into his fantasy. I went back to the f****y room to get my drink, a look of disappointment came over Conrad when he saw me coming down the hall, "I need my drink before I get started" I said. His face lit up "oh yes your drink" he said excitedly handing me my Rum and Coke. "I'll just be a little while" I said heading back to the guest room. I had worn panties and bras for men before and even a dress once, but I had never dressed completely as a woman. I stared at myself in the bathroom mirror what the hell was I thinking, Conrad wanted to fuck me, no doubt about that. I hadn't been fucked in years, I'm a cocksucker, I'm straight, I don't like men, but the thought of being Conrad's "girl" was strangely exciting. God, was I really gonna do this? I thought, my heart raced as I took the douche out of the box and put the nozzle on the bottle, I turned on the shower to let it get warm, then stood over the commode and douched. I took a couple of sips of my drink then got into the shower.
After showering and drying off I sat on the edge of the bed and painted my finger and toe nails pink, I had a few more sips of my drink as the polish dried. Next came bra, the inserts gave me the illusion of having small breasts, then garter belt, nylons and panties, a couple more sips of my drink, then the makeup, eyeliner, eyeshadow and foundation, luckily I've watched my wife many times over the years. I slipped the dress over my head and put the wig on, I finished my drink then put the pink lip gloss on, damn I knew Conrad would want to kiss me, I really hate to be kissed by a man and then he would try and fuck me, I still wasn't sure if I wanted to go through with this, we would see how convincing Conrad could be.
How in the hell did he know my sizes I wondered as I slipped the heels on, they were a little tight but I got them on and the other things all fit. I looked in the mirror, damn I was no fox, but I did look like a woman, it was time, I started down the hall. I remember thinking how silky and sexy I felt, then how hard it was to walk in heels as I made my way to the f****y room. Conrad was sitting on the sofa, "zip me up sweetie?" I asked in as girly of a voice as I could manage, "certainly" he said looking up at me "oh my" he gasped as saw me "Thank you Conrad" I purred batting my eyes then turning my back to him. He zipped me up then put his arms around me, holding me from behind he brought his face close to my ear "my dear you're absolutely lovely" he said softly in my ear then kissing and nuzzling my neck. I just knew he was gonna be kissy I thought, but I had to admit he had made me feel weak as he held me breathing in my ear. He had made me a fresh drink, "here you are Rikki" he said handing me my drink then sitting back down on the sofa, patting the cushion next to him, "sit here Rikki" he said. I hadn't thought about a name, but I guess Rikki was ok I thought to myself, my dress fell high on my thighs as I sat down next to him. I crossed my legs, my nylon covered legs rubbing against each other felt heavenly, how do girls stand all this stimulation I was wondering, I was lost in the moment, Conrad had put his arm around me, turning me to him he kissed me. I don't like men, I don't kiss and cuddle I was thinking as Conrad's tongue tried to find it's way into my mouth, but that's Richard, I'm Rikki I told myself parting my lips, tasting his kiss with my tongue. Conrad felt my breasts as he kissed me passionately, "Rikki" he breathed pulling me tightly to him, I felt his hand on my knee, I uncrossed my legs parting them allowing him access, my god I felt so lustful being the object of his desire. I fondled his cock through his pants, feeling it grow I unzipped him pushing my hand into his pants, I felt his hand between my thighs, I laid back as Conrad pushed my dress up and moved between my legs breaking our kiss he whispered "I want you Rikki' his hand stroking the front of my panties. I was trying to get his pants unfastened, he stood up and unfastened them and took them off. I slid to the floor on my knees in front of him, taking his cock into my mouth I sucked, licked and caressed him, I took his cock deep into my throat his balls slapping against my chin, I pulled off him , his cock slipped from my mouth with a loud pop "please baby, you know what I want" I teased smiling and licking my lips.Pulling my hair back behind my ears I took him back into my mouth and started sucking hard and fast, I knew he couldn't last long. "You sweet little cocksucker" he cried holding my head aa he filled my mouth with cum. "Mmmm, I love your cock" I purred looking up at him, doing my best to be girly. I stood up and he took me in his arms, he unzipped my dress as he kissed me, sliding it off my shoulders, then laying me back on the sofa he laid on me fucking his cock against mine through my panties as he kissed me, he kissed and caressed my body moving lower as he did. I felt his hot breath on my cock and balls as he pulled my panties down, then his kisses on the insides of my thighs above the tops of my nylons as he slipped my panties off one foot, then lifting my legs onto his shoulders he stroked my cock as he ate my ass. I'm straight, I don't fuck, but that's Richard, at that moment I was Rikki and I wanted Conrad to fuck me. "Oh baby fuck me with your big cock" I whispered. My cock exploded in a cum geyser running down Conrad's hand, he stopped eating me and started working his cum covered fingers into my ass lubing me. I laid there moaning as he fumbled with a condom, "no, I want to feel you cum in me" I whispered. His eyes lit up, then he laid between my legs, his unsheathed cock pushing into my ass "aaaaaaah stoooop" I screamed as his cock head pop into me. He stopped and held still, "Your pussy is so tight Rikki" he breathed in between kisses, he pushed again sliding more cock into me, I wrapped my legs around him pulling him into me until I felt his balls against me. he pulled almost all the way out then slowly push back into me "it's soooo good baby, fuck me.... fuck me now" I screamed. he fucked me fast and hard for several minutes, I was lifting my ass off the sofa meeting his thrusts as he pounded his cock in and out of my "pussy", he was definitely hitting the right spot, my cum shot up the length of my cock spewing on the both of us. Conrad was close, his thrusts had became short and fast "aah aaah aaaah" he cried out burying his cock balls deep in me, I could feel his cock spasm in me as he spewed in me. "Oh My God Yes, Cum in Me" I screamed as I milked his cock, I could feel the heat scalding my bowels as he finished and lay still.
"Stay with me tonight Rikki' Conrad suggested. "I can't, my wife isn't out of town" I said. His cock had shrunk and slipped out of me, he got up and went to the bathroom, I did the same, I found the things I needed under the vanity sink, I removed my nail polish and took a shower, when I came back to the f****y room I was once again Richard. Conrad said he would keep my wardrobe, it would be waiting any time Rikki wanted to play. I thanked him and left. It had been almost 40 years since I had let a man fuck me, and I wasn't a girl that time. So once again, I am not gay, I am a cocksucker, I don't covet men, I don't kiss and cuddle and I don't fuck, but Rikki just might now and then.
88% (21/3)
 
Categories: AnalFetish
Posted by covertcocksucker
4 years ago    Views: 1,349
Comments (4)
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2 years ago
Fuck this is a hot story. I would like to experience it from both perspectives.
4 years ago
I adore your stories. You are really talented.
4 years ago
Loved your story. I am about to experience my first time with a dick in my ass. My friend is a shemale and if all goes as planned, I am going to fuck her for the first time tomorrow. She hasn't said anything about fucking me but I am hoping she will and like you, I want her cum in my ass. We have promised each other that we will not masturbate until we are together again so there is going to be a lot of thick cum for both of us.
covertcoc...
retired
4 years ago
I took a little literary license with this story but it is based on an actual experience. I hope you like it.