13 comments/ 57726 views/ 52 favorites My Fun with Kelly and Jamie By: WhiskeyIsGood Here I was thirty' five years old, finally getting ready to tie the knot with a girl I had met and started dating five years ago. A lot' of my friends were busting my balls over it; telling me I was selling my soul. I didn't' take them seriously. I loved Kathy. Otherwise, I never would have asked her to marry me in the first place, right? Anyway, what did I have to complain about; I'd' had my fair share of sexual experiences over the years. I've' been with plenty of different women, all kinds of women. Women with blonde hair, red hair, brown hair. Women with big tits, small tits and' in between. Women with dominant personalities and women who just wanted me to fuck the hell out of them. Even two women who weren't' exactly....women, Yes, that's' right; I've' been with two transsexuals, or shemales as they liked to call themselves. Let me tell you the story about the time where I was "raped" by two beautiful shemales. Possibly the greatest sexual experience I ever had in my life, Thinking back on it, I am getting married now and this whole story happened right about the time when my friend Jay was getting married; in fact, I met Kelly and Jamie through some stupid bachelor party activity that we all decided to do for the fun of it all. I was twenty' two years old at that point. The night of the bachelor party, we all decided to go out to a bar and get some food and beer. We ate and we drank and we drank and we drank until it was pretty' late; probably around two o'clock in the morning if I had to be exact. Anyway, once closing rolled around we' all stumbled back to a motel up the street that we had decided to rent a room at, since we were staying in a city other than our own Into the motel room' we stumbled, laughing, slurring and goofing off like the drunken idiots that we were. Jay passed out a few minutes after we got there and so did our one friend Chris. Now it was just me, Mike and' Josh. Josh pulled his laptop from a bag sitting on the floor and flipped it on and within minute's he was online surfing the web for porn while Mike and I sat outside smoking cigarettes and bullshitting for a little while before coming back inside. That's' when we saw Josh on a chat room of some sort, "What the fuck are you doing," Mike asked laughing. I gave him as shove on the shoulder and grabbed a seat plopping down alongside of him as Mike sat on the opposite side and we both leaned in closer to the laptop screen. "It's a website called Chat for free," he said. "You talk to different people. There is a button at the bottom of the screen; when you're done with one conversation you click that and it sets you up with someone new." "Sounds like fun," I said. "So who are you talking to now," asked Mike. "Some girl named Maria; she's sort of boring though. So let's move on," Josh clicked the "next" button at the bottom of the screen and sure enough, the page began to reload before starting up again with someone completely knew. We sat around for a few hours doing this, talking to different girls and the occasional gay male that the room mistakenly set us up with'. By about four am Josh was passed out cold and now it was just me and' Mike. We took over the computer without even asking Josh, not that he could have stopped us in the goofing off kind of mood that we were both in. We surfed' the site for a few minutes, not really finding anyone interesting at first and eventually we started to get bored; but neither of us were willing to call it a night just yet. I clicked back to the main page of the website to see more information on it and to the left side of the page there was actually a row of different selections of the type of people you could talk to'. We scanned through it a bit and then started cracking up laughing when we saw the link for "Shemales," at the very bottom of the list. Thinking it would be plenty of fun to just give it a shot and see who' we came across, I clicked the link and we laughed as the page began to load. Soon we were being connected with people who like us, we were looking for shemales and plenty of shemales themselves though as soon as they would send pictures, we would realize they were not exactly all' that attractive. That's' when we would move on, We were just about to give up, when the screen blinked indicating that it was about to connect us with a new person. I suppose it was curiosity, or the fact that I just didn't' feel like calling it a night yet, but I decided to see what this person had to offer. And' of course, the first words they spoke had our attention with no effort at all, Stranger: Hi, I am Kelly and I am your hoe' baby. I looked at Mike and' Mike looked at me and we both busted out laughing before turning back to the computer and I started to type back. You: Hi Kelly, I am Tom. I'm twenty' two years old; how old are you? Stranger: Hi Tom, I am twenty' eight. "What do I ask next," I asked Mike running out of things to say. He leaned over and started to type. You: How big is your cock? Once again, we were both cracking up laughing as we waited for a reply to come through. Stranger: I am nine inches hard, and around 8.5 when not hard. I love my cock baby; I would love for' you to come here and suck it for me too, "Oh shit dude," I laughed hysterically. "See that Tom; she wants you to come suck her cock. Better get to it," "Fuck you," I said nudging his arm. Mike laughed, standing up and rustling my hair as he walked towards the bathroom still staggering slightly. "No man, Kelly is the one who's going to be fucking you," The bathroom door closed behind him and I resumed typing with Kelly. We went on for about five minutes, throwing sexual questions back and forth at each other until finally she shot me a photo of herself. Instant erection, I couldn't' help it even knowing that she had a dick in her pants. She was a beautiful, sexy red head with the bluest eyes I've' ever seen in my life. She had some sweet ass tits too. Then she sent me a second picture, this one of her cock and I found myself laughing again; but she definitely looked about the size she claimed to be. Just as I was about to start messaging her back, the conversation was' cut; obviously she had been the one to end it for whatever reason. But' now I was left here alone, bored and slightly aroused with no one to talk too. Mike had been in the bathroom for almost ten minutes; I assumed he had probably passed out with his head in the toilet. I got up to check on him briefly and sure enough, there he was passed' out next to the toilet. I flushed it and not wanting to carry his heavy ass to the bed I instead grabbed a pillow, brought it to the bathroom and set it under his head on the linoleum floor. Then I returned to the laptop and sat back down, glancing briefly at the clock at the bottom of the screen; it was 4:30 in the morning. I clicked the "start conversation" button and after a few seconds of loading a new conversation was' initiated; and it was obviously not going to be any less interesting than the one I had with Kelly. "Hey there baby, I'm your hoe'" Well that sounded familiar; I found myself wondering now if perhaps I was talking to the same person? You: Hi, I am Tom. Stranger: I am Jamie." Jamie...well, I was obviously wrong it wasn't' the same person. So now I was wondering if perhaps these two girls worked for some sort of company or something that had them come on here and talk to guys and that was their phrase or some shit like that. You: Jamie is a pretty name, Stranger: Thank you. I decided to ask out right; part of me was also wondering if this was indeed the same person, just using a different name. You: Why do you girls both use the same catchphrase? A few seconds passed with no response and I was starting to expect the conversation to cut. Then finally, the answer I was waiting for, Stranger: Cause' we can; you know that girl Kelly right? Here we go, I thought, I was definitely expecting her to tell me she was the same person just using a different name or something. This site operated by connecting you with total strangers and there was no option to create usernames; it was up to the person you were talking to to give you their name if they wanted. So' with all the people...and the top of the page read roughly about 28, 105 people...it was easy to end up talking to the same person once or twice without ever even knowing they were the same person, unless you exchanged names. You: Yeah, actually I just talked to her right before you lol. Stranger: Yeah we talked not to' long ago too. We want to rape you; it was her idea until she convinced me of it as well. Well that was far from what I was expecting, but it got a sort of rush going through me. Maybe it was the alcohol on top of the fact that I was actually kind' of horny, reading something like that just got the sexual nerves going. I had no idea and honestly what was I even thinking? Drunk or not, I knew these girls were both shemales, they both had cocks. You: Well its' not rape if the person is willing. Stranger: Oh so your' willing to have sex with me and' Kelly. You: Of course, though I should warn you I am a virgin. At least with Shemales that' is. I have only ever been with regular girls. Stranger: Oh don't worry me and Kelly will fix that up for you." You: Sounds good to me. What the fuck was I doing; this had all started out as fun, why the fuck was I talking to her so seriously now. Whoever looked at the screen' would never be able to take it seriously, but there was something deep down in my gut. My cock was hard and I had this buzzing feeling in the head, I was so turned on by this conversation alone, it just wasn't' even funny. I should have logged off and gone to bed at that point, no questions asked. It was nearly five in the morning anyway...but I couldn't' bring myself' to end the conversation. So' we carried on for another fifteen minutes going back and forth with our sexual flirtations. Eventually, she started telling me what she and Kelly wanted to do to me, everything from handcuffs, to pinning me down, to her throat fucking me while Kelly rammed my ass. Then we started talking about how big Kelly told me she was. I asked how big Jamie was and she replied that she was only about eight inches or so and had always been jealous of Kelly because she was the bigger out of the two friends. Then she sent me a picture, as Kelly had done. Jamie was a bit shorter than Kelly she had blonde curly hair, green eyes and a cute little nose. She was just as sexy as her friend was though, You: Well you both put me to shame. So I guess it only makes sense that I would be the one getting plowed, since your both bigger than me lol. Stranger: How big are you Tom lol You: Probably around average, sadly Stranger: Aw' that's' too bad. I guess we are going to have to ram you then. I was looking forward to a nice pounding myself, but I guess not. We'll' have to get you instead, I figured at this point that it went without' saying no matter how horny I was and how horny these two claimed to be...this wasn't' actually going to happen. They probably weren't' even anywhere near where I was right now, for all I knew they lived halfway across the damn country or they lived in England or something like that. So I went ahead and just carried it on for the fun of it as I had been doing in the beginning. You: Well I am ready for you two to rape me, Stranger: Well what are' you waiting for Tom, come get us. You: Well, should you two be' the ones coming to find me? I don't' even know where you are anyway. Stranger: Where do you live? Again, figuring these two lived halfway across the country or world for that matter, I went ahead and told her where I was at the current moment. In a motel' in New Jersey, To my surprise, they apparently did not live far from where I was. I started to feel sick to the stomach the more the conversation progressed and the more it started to seem like they actually wanted to come meet up with me. I still kept trying to convince myself though that there was no way this was really happening; there was no way these two would really come out here to meet. They were probably just saying they lived as close as they said they did, they probably did not really live anywhere near here at all. Stranger: We cannot be there until morning baby. Is that okay? You: Should be fine. I was ready to sign off at this point and sleep...I had convinced myself they were just yanking my leg at this point and decided it was time to end this. She promised they would be here in a few hours and laughing to myself, I went along with it saying I could not wait to see them. Then I logged off, crawled into bed and I was asleep in minutes. I woke to the sound of the motel room door shutting and I jumped in my sleep opening my eyes. Looking around the room, it took me a few seconds to remember where I even was; Jay's bachelor party had been the night before. Now I remembered everything, all of it came rushing back...even the website on Josh's computer and the conversation with those two transsexuals, Kelly and Jamie. Groaning, I sat up, rubbing my head at the feeling of this morning's hangover. That's' when I noticed the others were not here...Josh and Jay were both gone, I got up and checked the bathroom and even Mike was gone. The bathroom was wet; water dripping from the faucet in the shower indicating that someone had recently used it to clean up. I came out of the bathroom and found a note that I had missed sitting on the kitchen table. It read: Tom. We took off early. Did not check out though, so when' you leave make sure you turn in the key and pay the motel manager. We left our money in the top drawer. Don't' worry pal, not leaving the whole tab on you. Mike, Well at least they were not leaving me to pay for the entire thing on my own. I would have been pretty pissed off if that had happened. Sighing, I crumpled up the note and tossed it in the trashcan before grabbing my duffle bag and pulling out a towel and some fresh clothes. I made my way to the bathroom and removed my old t-shirt and shorts, which I had slept in. I was just about to turn on the hot water, standing in the bathroom with nothing but my boxers, when I heard a knock at the motel room door. Groaning in frustration, I walked towards the door hoping it was not the manager getting ready to kick me out'. If it was' hopefully he would at least let me shower beforehand. I peeked out the curtain over the window first; I could not see all' that well as the sun was shining in and making it difficult. As my vision cleared though, I thought I saw two women standing there in front of the door in skimpy looking clothes. Confused, I backed away from the window and unlocked the door turning the knob and pulling it open. "Hey," said the one girl with short red hair smiling seductively at me. "Uh...hi," "Are you Tom," the blonde girl asked. "Uh, yeah I am'." I was trying to figure out how these two girls knew my name, or who the' hell they even were for that matter. Then as I looked closer and examined the seductive grins they both had, it dawned on me what was happening. The red head was the exact same girl I had seen in the picture that Kelly sent me, and the same went for the blonde'...that was obviously Jamie. I couldn't' believe this was happening, this was real, they had been serious when they said they were nearby and they would be here by morning. "Uh...you were being serious?" "Of course we were," Kelly' laughed. "You thought we weren't?" "Well it's just...I don't know. It's' the internet, it isn't' easy to just believe what random strangers that you just met tell you. I thought...it was a game," "So," Jamie said with a start. She leaned into the doorway real close to me and I could smell her sexy perfume mixed with a faint odor of cigarettes. She was wearing purple lipstick. "You don't want us to...rape you?" Kelly leaned in alongside of her and whispered in my ear "Are you sure?" She grabbed my package and squeezed and I groaned as they both pushed me into the room and Jamie brushed past me. Kelly shut the door and pushed me up against the wall, pinning me there as she continued rubbing my cock through my pants and smiling at me the whole time. I just stood there...completely shocked and frozen. Still unable to believe that any of this was actually real, "So," Jamie said. "Here we are." Kelly smiled at her friend then back at me and leaned in kissing me on the lips and I broke right away. Her lips were so soft and she tasted like strawberries; I just couldn't' help but kiss her back. I felt her tongue slip into my mouth and it started fighting with my own. After a few minutes of this, Kelly was kissing me on the neck while Jamie kissed, licked and sucked my nipples. I was so horny, Yet I still clung to that one thought that this was so very far from a straight heterosexual act. What the fuck was I doing? I had no time to keep thinking about it as I watched their clothes start to come off now, one by one until they were both in front of me in nothing but their panties. I could see the outlines of their cocks, but Jamie lifted my gaze back up to her tits as she continued kissing me and reached into my boxers to stroke my cock. She pulled my boxers down and dropped to her knees, leaning in and swallowing my dick in one swift move. I groaned, her mouth was so wet and hot and it felt incredible. As Jamie sucked my cock, Kelly laid' down on the mattress and' slid out of her panties nice and slow so I could watch as the slipped past every curve. Finally, they were off and I was staring at her huge cock, which was throbbing and leaking pre-cum as well. Kelly wrapped her hand around her shaft and started stroking it nice and slow as she watched Jamie continue to suck my dick. Then, she pulled away, stood up and pulled me away from the wall leading me towards the bed. She tossed me onto the bed and I landed in the most awkward of positions...with my face right in front of Kelly's dick. "Mm, perfect," Kelly said running her hands through my hair. "C'mon baby," I leaned in and wrapped my lips around her cock. I took a few moments to register the taste; it wasn't' bad. She tasted clean, like she had probably just showered not too long ago, though there was a faint odor of sweat. However, even that seemed to' simply' arouse me further. I inhaled the musky aroma of sweaty balls and moaned as I felt Jamie slip underneath of me and' take my cock back into her warm wet mouth once again. So now, I was sucking Kelly while Jamie was sucking me and stroking her own dick all at the same time. Then, I felt Jamie's hand grab at my ass and squeeze before giving it a slap. The loud sound of something smacking up against flesh echoed through the motel room like in a porno. I felt her hands pry my ass cheeks apart and one finger traced over my anus; I tensed up just a little. She pulled her finger away and stopped sucking my cock just long enough to wet her finger before returning it to my asshole. She swallowed my cock once more and I gasped, as I felt her wet finger slide into my hole nice and slow. Even as she began to finger fuck me, Jamie continued sucking my cock like an expert and I was starting to feel like I was getting ready to cum, she stopped, and I felt her warm breath suddenly over my ass and then jumped in surprise at the feeling of her wet tongue diving into my asshole. She was giving me a rim job, the first time I had ever had one in my life. I stayed focused sucking Kelly's cock while Jamie worked my asshole with her tongue and fingers and Kelly smiled and laughed. "Someone's enjoying himself," she said. My Fun with Kelly and Jamie "I guess you're not so straight anymore, now are you?" "I told you," Jamie said stopping what she was doing briefly. "I told you Kelly and I would take care of the whole fact that you've never been with girls like us before. And' I knew you'd enjoy yourself too," I groaned as she dove' back between my ass cheeks again and that's' when Kelly slipped out from underneath of me and I sunk forward into the mattress. Jamie laughed, stopping what she was doing again and squeezing my cheeks then giving me another slap. "I think he's ready," "Good," Kelly said coming over with what appeared to be a giant blue dildo. "Move over then, and let me get a piece of that sweet little virgin ass." "No way," Jamie said laughing. "I promised him...I would be the first to ram my cock up that tight little asshole of his." Kelly sighed disappointed and handed her the dildo before taking a seat in the corner of the room and returning her hand to her cock, which was still wet with my saliva. I waited anxiously as Jamie teased me with the dildo, running it against my asshole for a few moments before pushing it into me. I bit my lip tensing up and then moaned at the feeling of fullness. It was much bigger then her fingers, even after she had three of them inside of me minutes ago. I did my best to accommodate though; I tried to relax my whole body and all of my muscles. I had to get use to this, if the dildo felt this big then I could only imagine what her cock would' feel like...or Kelly's for that matter. "You like that baby," she asked as she slid the dildo in and out of my asshole. I groaned, gripping the pillow as she fucked me with the toy for a few more minutes and then pulled it out and set it down on the side of the bed. She grabbed a purple bottle of what I assumed was lube, squirted some all over my asshole and even more onto her hand. I tensed up as she poured it on my ass...it was cold. I heard a squishy sound and looked back to see her stroking her cock with the hand she had poured the lube into. "Just getting us both good and' ready baby. The more lube, the less it hurts; no such thing as too much lube Tom, never forget that." I waited anxiously until finally, I felt the bed shift and the tip of her cock pressing against my asshole. Here it comes, I thought, the big moment. Literally, the "big" moment, I sucked in a deep breath of air and felt her push right into me. I couldn't' believe how easily she just slipped right in, and I hardly even noticed until she was buried up to the balls. I felt my entire body begin to shake; I had never felt anything like this in my entire life. She grabbed me by the hips and started ramming in and out of me, pounding my ass good and hard. As she did, Kelly came back over and' got onto the bed on her knees right in front of me and shoved her cock back into my mouth. Now here I was taking it in the ass from one hot shemale while another gagged me with her cock. As Jamie started fucking me harder and faster, my body started shaking more violently and I could feel my cock straining, dripping cum all over the bed. Then finally, I howled in pleasure as Kelly pulled her dick from my mouth and I felt my anus tighten up and clench itself around Jamie's cock squeezing her until she too started crying out in pleasure. My own dick jerked and shot cum all over the sheets, probably the biggest load I had ever shot in my life. It felt incredible, I was sweating so much and breathing so heavy and then I felt Jamie ram her cock all the way into my ass, holding her position and I felt her warm sticky cum filling me up. I could feel it running out of my ass and down the back of my legs and Kelly laughed as she watched the expression on my face. "That felt good didn't it baby," "Oh fuck," I groaned. "Oh fuck is right," Jamie' sighed. Kelly moved out of the way and I once again sunk forward into the mattress with Jamie still buried inside of me. I could feel her weight pushing me further into the mattress and I could feel her sweat dripping all over me. She slowly pulled out finally, and started making out with Kelly right in front of me. I rolled over, watching them with fire in my eyes; they noticed the look on my face and broke their kiss. Jamie moved in and started making out with me while Kelly started sucking my cock. She sucked me until I was good and hard again before she lifted my legs up all the way to my shoulders and got ready to have her own fun. This was the first time I had really' gotten a good look at just how big Kelly actually was; and she was huge. Very thick, and very big and I waited nervously as she pressed the head against my asshole which was still wide open. I gasped and then moaned, as she thrust right into me. As I moaned, Jamie kissed me again to quiet me and Kelly started fucking me. She held my legs up as she thrust in and out, our bodies slapping together. The air smelled of sweat and sex and the room was' filled with the sounds of our soft moans and the smacking of lips as Jamie and I continued kissing. Eventually, she backed away and' Kelly dropped my legs and I wrapped them around her waist. She rammed all the way into me, leaning right over me so her tits were right in my face as she pounded my ass so hard the entire bed shook underneath of us. I was getting ready to cum again, and I grabbed my cock and started furiously stroking it and screaming in pleasure; whoever was in the room next door, there was no way they did not know what was happening right now. Finally, I exploded, my whole body locking up on me and I couldn't' even believe how good this felt. Kelly pulled her cock from my ass, leaving me with a sudden feeling of disappointment, but it was quickly relieved when she sat on my chest and exploded, firing off a huge load right in my face. When it was over, I lay there breathing heavily, Kelly still planted on my chest and Jamie started licking her cum off, of my face. Kelly collapsed onto the bed next to me and Jamie crawled up on my other side, resting her head on my chest. My body ached and I was exhausted; I still couldn't' believe this had happened. "You're a pretty good fuck," Kelly said. "Isn't he though," Jamie said and both girls started laughing together and discussing right in front of me, just how good it had been to fuck my brains out. I couldn't' help but laugh at their conversation. "Maybe next time," Kelly said grabbing my cock. "You can have a piece of our asses, if you want." "I think I'd like that," "He's only average," Jamie laughed. "But I'd still like that too." So' that's' the story of how I was ravaged by two beautiful shemales; and yes, we did eventually meet up again for another round and I did get to fuck them both in the ass...Jamie, Kelly and I actually had quite a few sexual encounters together. Actually, they were both here at my wedding. Of course, my wife to be had no idea they were actually' shemales, nor did she know about our past sexual endeavors together. And' there was no reason for her to have to know. Kelly and Jamie were not here with the intent of stealing me away from Kathy, though they probably would have loved to. They were mostly here as my friends. Who knows...maybe I will tell you about some of our other fun times together.