Jenny Learns Her Place

Anal

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over. I’d known Bobby since grade school and had even enjoyed a couple of jack off sessions with him during high school but I’d never thought of him in this sense. When I saw him enter the bar I’d recognized him immediately but it had taken him longer to figure out who I was since I was now dressed as a woman. We were halfway through our second drink and his hand was high up on my nylon clad thigh before I saw the light come on in his face as he recognized me. When he did his hand slid the rest of the way up under my skirt and rested on my panty covered dick. “John?” “Not anymore, sugar, call me Jenny,” I had replied with a smile and rested my dainty hand on the lump growing in his pants. “You know, when we used to jack off together I wanted to do so much more but I was afraid.” “I wish I’d known back then,” he answered and smiled. “I thought you were very cute for a guy and I spent many nights lying in bed and jacking off while thinking about you.” Blushing brightly I replied, “So did I.” After that we danced to a slow song and before it finished we were kissing like lovers. “I want you, uh, Jenny,” he whispered in my ear, his hand resting gently on my ass. He lead me back to our table so we could finish our drink, all the while his hand under my dress and lightly stoking my hardened little dick. Setting my glass on the table, I said, “We better get out of here before I make a mess.” “Want to go somewhere and make a mess together?” “That sounds wonderful. We can go back to my place,” I told him as he lead me to the parking lot. “Where do you live?” “Same place. My folks died in a plane crash a couple of years ago. I kept the house since the insurance paid it off. Of course I’ve made some changes, as you’ll see.” The changes, which I had become accustomed to by now, were very obvious to anyone who’d ever been there before. “I’ve got to know, Jenny. How often do you dress up? I mean, on weekends or after work, or what? You know, I’ve always thought you’d look good as a girl and what I see confirms that absolutely. You look better than good, you look fantastic.” “Thank you, kind sir,” I laughed in response. “But to answer your question about dressing like a woman; all day, every day.” “Really? Cool! More than just the average crossdresser, then. Are you thinking about going all the way?” “Oh sure, I think about that daily but I’m not sure I want that. I mean, if the right man wanted me go that far, I might, but so far I’m not planning on it. Hell, getting breast implants hurt bad enough, I can only imagine what the other surgery would feel like. But I have given some thought to having my testicles removed since I’m not even remotely interested in reproducing, especially since I can’t get pregnant.” “Real tits? How cool is that?” “They’re real between hormones and implants,” I answered, laughing. Looking at me he smiled and said, “I’d surely love to get a taste of those babies.” “You would? Don’t you want to pinch and twist and fondle them as well?” “You bet your sweet ass!” Leaning over the console, I began fumbling with the zipper of his pants and before very long his cock was standing up proud and stiff. Moving closer, I could smell his maleness and it was quite intoxicating. I started off by licking the bulbous head, swirling my tongue all around it before even trying to get him in my mouth. Sucking cock was something I loved doing and I knew the guys I’d sucked in the past liked what I was doing. Slowly but surely I worked my lips around him and began doing what I knew men loved which was taking all of their cock, no matter that I was always spared the last couple of inched because of the material and zipper. “Damn, Jenny, you sure know how to use that mouth. Why the fuck I didn’t press the issue a few years ago, I’ll never know.” I looked up momentarily when the car left the freeway and I knew where we were. I only had a few minutes to get him off before we arrived but I was confidant. Before taking him back into my mouth I said, “Cum in my mouth, baby.” Stopping at a red light, I could sense his urgency so I worked my head up and down faster and faster. We took off from the light and I kept on going even though I could hear a car driving beside us and getting a good view of what I was doing. We’d just barely stopped at the next light when I felt his hard cock trembling and his breathing becoming very ragged. I think we sat through a green light and so did the car next to us because Bobby was busy trying to drown me with hot, delicious, cum. When I sat up and wiped my lips, the car next to us honked and drove away. Smiling güvenilir bahis at Bobby I said, “That’s what it costs you to play with my titties. I like getting paid up front.” “What will it cost me to get in your panties?” “A dance, a kiss and a feel.” “Great!” We pulled into my driveway and parked beside my little car. I’d taken a taxi to the bar just in case I was too tipsy to drive home or if I got lucky. By the time we got to my front door my dress was completely open and when I opened the door my dress fell off. Bobby kissed me long and hard, the tour of the house forgotten. We left a trail of clothes from the front door to the bedroom, mostly his because all I had left to take off was my bra and panties. He insisted that I keep on my heels, stockings and garter belt but other than that I was naked. Several guys liked me dressed in this manner and some guys liked me nude; either way was fine with me. Even though I’d given plenty of blow jobs while fully dressed or had been bent over to get fucked with my skirt up on my back and his pants around his ankles, my personal preference was both parties fully nude. Bobby gently lowered me to the bed and then joined me. He played with my titties, sucking, pinching, and then rolling the nipples between his finger and thumb and I was growing hotter and hotter. When he flipped me over and pulled me to my knees I was expecting to feel his big cock trying to enter me but I was pleasantly surprised. Bobby pressed his lips against my puckered little hole and began licking me before sinking his tongue into me. This was definitely a first for me and I loved it. “Holy shit, baby, that feels absolutely wonderful!” I growled between gasps, my entire body shivering with lust. “You’re driving me crazy! Oooohhhh yyyesss! Oh baby, please fuck me! I need to feel your big cock deep inside me! Fuck me! Fuck me!” Bobby straightened up and moved closer to me, aiming his rigid cock at my tiny hole. He moved against me and began pressing forward, slowly forcing his dick inside. “Oh yyyesss! Oh, fuck it hurts! Shit, it hurts so fucking good! Fuck me!” I squealed again and again, giving myself completely to him. Suddenly he was buried completely in me and remained still so I could adjust to him. After a few minutes I began moving on him, pulling off his cock and then slowly pushing myself back on him until he picked up the rhythm and began moving on his own. “Yyyesss! Yyyesss! Oh yyyesss! It’s so good! Fuck me good, baby! Oooohhhh fuck me!” Thirty minutes later he was still plowing into me, faster and harder, giving me the best fucking I could remember. “I’ve wanted to do this for years, Jenny, ever since high school! You’re ass is so hot, so perfect, and so delicious!” “And it’s all yours,” I responded, my words broken by gasps. I wanted him to cum inside me more than I’d ever wanted any man. In mid stroke he shuddered and jerked, slamming his cock into me before hammering me with a lustful frenzy. My body began to shake once again but my cock had nothing left to spew. I was cumming again, but in a manner so entirely different than a regular orgasm. This time my orgasm seemed to emanate from the center of my being. When his sperm blasted into me I thought I’d died and gone to heaven. Bobby kept on pumping his hot cum into me until I felt it oozing down over my own spent balls. We collapsed onto the bed in a mass of tangled, use flesh. He rolled me over and kissed me again, holding me close to him. “That was fantastic!” I gasped. “I’ve dreamed of this forever but I never thought it would happen. Now that it has I want to do it again and again.” “Do you say that to every girl you fuck to hell and back?” I asked, holding him tightly. I wanted to tell him how much I wanted the same thing. “Would I lie to you, sweetheart?” “I certainly hope not.” “I won’t,” he said and lightly kissed my lips. “I’ll hold you to that,” I replied and smiled at him. “Well you just go ahead, little lady,” he answered using a decent John Wayne voice. “Now get your ass out of bed and let’s go eat.” An hour later we were sitting in an all night cafe. Bobby had insisted that I go without the benefit of panties, bra, or anything else other than heels and dress. We ate and talked and while we did so his hand moved under my dress and fondled my little dick. “I’ve always thought your clit was so cute,” referring to my dick in the proper feminine term. “Thanks,” I replied, smiling broadly. “And I’ve always thought your cock was lovely but now I know for sure it is.” Some men liked me being very well under endowed while a few would have preferred me being much larger, I was happy with my little tool, especially since I always assumed the female role during sex. If a guy wanted me bigger so I could fuck him, I used a strap on dildo. This was an act I rarely was asked to do and really didn’t like it because I wasn’t the dominant type. By the time we got back to my house it was close to three in the morning and by then I was dead tired. However, I wanted to güvenilir bahis siteleri get to know about Bobby so I asked him if he’d like to spend the night, which he did. Very rarely did I ever ask a man to stay the night. I might sleep with a man in a hotel or at his place but hardly ever did he anyone stay at mine. Somehow we managed another session of fantastic sex before falling asleep. The next morning I work up and put on a short robe before quietly going to the kitchen to make breakfast. Bobby met me there before I had everything ready and sat at the table drinking a cup of coffee and watching me. “You can cook, huh?” “Of course. If I remember correctly you used to like your eggs fried as hard as a rock and your bacon crispy.” “Damn, you remember that?” “I remember everything,” I said with a giggle. We finally sat to eat breakfast and talk a little. “Do you have any plans for today?” Bobby asked between mouthfuls. “Not a thing.” “Would you like to go to a movie?” “A date?” “Yes, a date. A movie and then something to eat and then …” “I’d love it; all of it.” “Great. After breakfast I’ll need to go back to my hotel and change clothes. So after a shower and a shave, I should be back in two or three hours.” “While you’re gone I’ll do the same and be ready when you get back.” I know it was just a date, but I’d only been on two dates before this and they were just driving around for a while and then parking somewhere quiet and having sex in the backseat of his car. The vast majority of my encounters had just been for hooking up and getting laid or sometimes just sucking the guy’s cock. Not that it was something I didn’t care for but this time I was going on a real date and I was very excited. After eating and deciding which movie to go to, Bobby dressed to leave. Before leaving, however, he kissed me hard on the lips, his tongue delving inside and searching every niche and cranny of my mouth completely while his hands opened my robe and gently roamed over my nakedness. Even though I was excited about going on a date with him, the thought of spending the day in bed and giving myself to him over and over was equally as exciting. “You’re so smooth and sexy, Jenny. I never dared to dream we would ever be doing this even though I’ve wanted to for so long,” Bobby whispered. “I know what you mean. I’ve longed to be in your arms since before we ever did anything,” I replied and then raised up on my tiptoes to give him another kiss. I don’t know how many men I’d kissed but Bobby felt so different. He broke the kiss and patted my bare ass before saying, “I better go or we’ll wind up spending the day in bed. While I’d love to do that, I want to take you out.” When Bobby returned he was in a nice sport suit and I was wearing a knee length, off the shoulder, white dress, nude stay up stockings, a pair of sheer white panties and a pair of pumps with four inch heels. The heels didn’t even come close to making me as tall as Bobby, who stood an easy six feet tall while I was barely five feet four inches in my stocking feet. “Are you sure you don’t want to spend the day in bed?” I asked after I kissed him. “The temptation is great,” he replied, “but I want to take you out to a movie, then to dinner, and then I want to come back here and fuck your brains out.” Smiling, I replied, “It all sounds good to me.” He took my hand and led me to the car, opening my door and helping me inside. The guys I was usually with just let me walk around the car and climb in on my own. It felt nice to be treated like a lady instead of the easy tranny they knew I was. When we arrived at the cinema Bobby took my hand and we walked together this way. He seemed to not care that he was being seen in public with a transvestite sissy, cock craving degenerate. Of course, I passed with ease and only anyone who knew me personally would know that I’d fuck at the drop of a hat. To be sure, I knew quite a few women who would do the same thing. We were seated in the theater with several minutes to spare and Bobby said, “I was married for a while.” “And you’re telling me this because …?” “I just wanted you to know. I was married to a great woman for almost two years. We broke up because I had a really hard time keeping it up for her.” “I find that hard to believe,” I giggled, thinking about how many times, and how quickly, he had gotten hard for me. “That’s what you do to me, Jenny. You drive me completely insane with lust.” “Or maybe you’re just a bit more bisexual than you imagined.” “I’ve thought about that. Even thought that I was totally gay. I’ve been with a few men and even a couple of trannies, and yeah, I could perform okay, but every time I was with any of them, I always thought about those times we jacked off together.” From the way he had reacted yesterday I had a hard time imagining him as being unable to perform. I wondered what other things he might have in the back of his head and was afraid to voice them for fear of being ridiculed. I came to a decision that, unless he iddaa siteleri wanted to hurt someone, I’d be willing to do anything he wanted. I mean, when you come right down to it, I was fairly kinky and very liberal minded. I had posted hundreds of photos on the Internet and about half of them had me in various compromising positions with one, two, three, even up to six guys at the same time. Other photos were of me in various states of dress from the very nice to the very sexy, to panties and bra, to nothing at all, both in private and in public. During the movie Bobby kissed me several times, felt my titties, sent his hand under my dress to fondle me, but all that came of it was that I got super horny. I would have given him a blow job but the movie ended before I got the chance. From the cinema we drove to a very nice Italian restaurant and enjoyed some very exquisite food while we talked. Our conversation ranged from the movie to some more interesting and personal things. “Have you ever had sex in a public place?” Bobby asked out of the blue. “Yea, a couple of times, unless you want to include the backseat of cars,” I replied. I’d thought about lying but I didn’t have any idea if he’d seen any photos of me online. “Did you like it?” “Yep. And to answer your next question; yes, I’d do it again with the right guy. Uh, that means I’d do it with you if you wanted.” “That would be cool. My ex-wife would only have sex in bed with the lights out, not even in daylight.” “Bummer. Was she ashamed of her body of something?” “She thought that any one that would show their body was a pervert.” “Well, I guess I’m a pervert,” I laughed. “I think my body is pretty nice and I’m proud of it. I walked in a Pride parade a few years ago and while I had to wear clothes of some sort, I left very little to the imagination. I wore a g-string and a super small bikini top and that’s all. I bet I was photographed a few hundred times. I like to be photographed.” “I’d like to take some pictures of you, Jenny.” “Go for it!” “I will,” he smiled. “Hey, when was the last time you had a spanking?” “Oh, wow, let me think…” “What would you do if I pulled you over my knee and gave you one on your bare ass?” “Scream. Shout. Kick my feet if I could. Maybe cry. Maybe get so horny I’d want to fuck you,” I answered and grinned. “Really? Interesting. How about bondage? Ever done anything like that?” “I’ve been tied up a couple of times and used very nicely. One guy I dated liked to tie me up and fuck my mouth really rough and then cum on my face. He was more into the power thing and humiliation than into me.” “Well, I’d like to tie you up and use you, but I’m not into humiliation or anything like that. Well, maybe a little bit,” he added with a smile. “Don’t get me wrong, there’s a lot of humiliation involved in most BDSM scenes, especially if a third party is involved or even just watching. Hell, spanking can be humiliating all by itself, which it’s supposed to be. For instance, my ex sister-in-law was a dyed in the wool exhibitionist, it both excited and humiliated her to be naked in front of other people. Her husband used to make her suck his dick in front of me and my wife. She’d be totally naked while doing it. Or he’d make her go into a convenience store late at night completely nude just to get him a pack of cigarettes.” “And she didn’t have a problem with that? Wow! Well I trust you, Bobby, and if you want to tie me up and do all sorts of nasty, sexy, fun things, I’m your girl. I’m also a bit of an exhibitionist in that I love getting my picture taken nude, clothed, or doing something very naughty.” Bobby smiled. “I know, Jenny, I’ve seen your pictures on the Internet but I didn’t know it was you until I saw you last night.” I blushed brightly. “Then you know I’m a slut.” “So?” “Well that’s how I make extra cash.” “From the website or did those guys pay you?” “The website. I’m a slut, not a whore!” I protested. “Cool! You know, we could collaborate on some things and maybe generate more income.” “Yea? What do you have in mind?” “We could give your customers variety by adding a couple of more girls like yourself. Add in a little BDSM, a few more gang bangs, some of the girls getting together, you and one of the girls, all sorts of kinky stuff.” “Well, it wouldn’t hurt my feelings any to generate more income. I know a few girls, not many, and I have no idea if they’d even consider doing anything like this.” “How about this, a web site with all the girls in various stages of undress, all the way to full nudity and erections? We’d have to launch it with at least a hundred full photo shoots so we could have a couple of thousands pictures for the customers and add at least one per week along with videos. Yea, yea! One site for the girls in various states of getting naked, one site with definite X-rated material girls fucking men, men fucking girls, sucking going both ways and girls doing girls as well, one site with bondage and spanking and all the other stuff that goes with it. We could even graduate to chat rooms if we can get enough girls to man the place twenty-four seven. “ “Wow! You’re just full of ideas. Are you planning on having sex with these girls?” “Having sex? I hadn’t even thought about that.” “Good answer,” I giggled.

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