Un-Expected Threesome

So we planned on meeting one evening in a motel room. I was just going to dress up as Kristen and you were going to teach me how to do make up or at least get better with doing it myself, Not expecting anything out of the ordinary with it. So after you dolled my face up with foundation and blush you did my eyes with a purple tint and I put on a dark pink shade of lipstick. I even let you shape my eyebrows a little. I then went into the bathroom to dress.

I put on a pair of white G-string panties and white stockings and garter. I then slipped on my pink plaid schoolgirl skirt and pink blouse and finally adding my dark brown wig. Oh and of course completing my look with my pink heels. When I finished I stepped out of the bathroom and like last time you were shocked. Again you said I looked very pretty and that I could pass as a woman. That made me feel confident with it and I started to feel even more feminine.

I then started posing for you while you took pictures of me all dressed. I felt even sexier trying different poses that I've seen others do in the pictures I've seen. About that time I started to feel a little daring and wanted to try walking down the motel's hallway hoping to be seen. You stood by the open room door while I sexily walked slowly down the hallway. The motel wasn't that full but it still seemed fun. I then decided to go out in the parking lot and pretend to get something from a car while you use my cell phone to video me.

It wasn't really that late, going on 9pm, when headlights from an approaching car came into the parking lot. Thinking it was just passing by I was getting a little excited because someone was going to "catch" me dressed as Kristen. But instead of passing through the lot, the car began to park two slots over from the car that I was pretending to be mine. But I didn't panic. If I had I probably would've even drew more attention to myself. I glanced over at a male figure in what looked like a 4door BMW. I saw just one person in the car with the available parking lot lighting and it looked like a male figure behind the wheel. I then slowly turned back toward the motel door and motioned for you to slowly walk back to the room. I then slowly entered the hallway again, again not to act startled and not to be in a rush. I heard the car door shut and heard someone get out. About the time I got through the door I heard it open again. I quickly glanced back and seen a guy dressed in a suit entering the doorway. I started walking a little quicker without make it obvious. In a way I was excited shaking my ass a little for him to see. I was a good 10 yards ahead of him where you were holding the door open and I caught one more glance at the suit wearing man. He was very handsome and looked in pretty good shape. I decided to do even something braver to impress you. I turned to him smiled and said; "good evening sir" right then you grabbed my blouse and pulled me in. I heard him say just a simple "hi" as you shut the door.

While back inside the room I felt such a rush. You were trying to calm me down but I was still feeling feminine and wanting to be slutty. We started talking about what just happened. Laughing at the silliness. We said a lot of "what if's" like what if he was closer behind me, what if he started talking to us. Adding what if he knew I wasn't really a woman. And then the "what if's" turned into what if his room's close by and what if we go knock on his door? I was starting to think about him. An older looking handsome guy probably here on business. Alone in his room probably bored needing to unwind from his stress. That even made me more wanting to be daring.

At that time I started imagining what he'd look like getting out of that suit and tie. I said to myself, "maybe now's a chance to show her what happens to Kristen when she's dressed and gets in her gurl zone" I started to tell you things like, maybe he's not alone, maybe he has his wife and k**s there, and maybe he didn't even notice us that much. Then I started telling you things like, “he wasn't bad looking, he seemed like he had a nice body and I wonder what his cock looked like?” You just started laughing again thinking I was really losing my mind and just pretending I wasn't really thinking those things. But I just kept picturing him undressed.

Then the room phone rang. We both jumped startled thinking why would anyone call the room. Maybe someone ran into my truck or maybe there’s an emergency and we need to evacuate. Both seemed like the worst. with me in drag having to leave the room or change out fast not being able to get all the makeup off my face. I told you to answer it but you said no you answer it. So I picked up the phone and shakily said, "hello”. To my surprise it was a male voice that said, “hello, I seen you in the hallway earlier and you told me "hi". I was wondering if you and your friend would like to come to my room for a drink.” I hesitated a bit and then said, “I'm not sure let me ask my friend.” he then said, “Well if you'd like I'm two doors down on the right. Just knock and I'll let you guys in, if you don’t show I understand.” I said, “Ok thanks for the invitation but I’ll need to discuss it with my friend. If we don’t show up in the next 10 minutes then we’re not interested.”
I then told you what he said. At that time you were even getting excited but also hesitant. I even started having 2nd thoughts not knowing what to expect and plus the fact is he's just a stranger. Like I always do, I talked you into going. I said how bad could he be, he was driving BMW dressed in a suit, he looked clean cut enough. I told you if either one of us gets a funny feeling or bad vibes, we'll make sure we head out the door quick. I said he'll probably change his mind real quick when he realizes I'm just a guy dressed as a girl. Besides I could always go back to man mode if I ever feel a threatened and have to fight. So daring, excited Kristen talked you into going to his room.

While leaving our room it still felt like the motel didn't have very many customers. It was very quiet and his room was away from the front desk. You followed close behind me as we approached his room door. I softly knocked on the door and he said, “Come in its unlocked.” I think we both were shaking when I looked at you and whispered, here goes nothing. The room had two beds. The television was on some music channel. Not too loud at all. There was one suitcase in the closet, a brief case on the table and a suit coat and tie thrown over the back of one of the chairs. There was also a pair of dress shoes on the floor under the clothes rack. We both could see him in the bathroom area brushing his teeth in the sink. I don't know what you were thinking at this point. You were probably busy with your own thoughts but I did feel that you were just as nervous as I was with what was going on. I was just looking at him looking at us through the mirror. He had his dress shirt halfway unbuttoned over his t-shirt and his dress slacks and socks on. Kristen couldn't help but check out his tight round ass in those tight slacks he was wearing as he was leaning over rinsing his mouth. He said," Have a seat I'll just be a minute." You guys could sit on the bed or have a seat on the chairs. I sat down on the bed while you sat on a chair next to me. Kristen was the one who started the conversation asking him where he was from. He said he was from Wyoming and down here with some kind of insurance conference. He said it was his last night here and thought he would relax a bit before heading home tomorrow. He said he just got done with his last meeting when he arrived back to his room a little bit ago. He said he seen us walking in the hallway and thought we might like some “guy” company. We then looked at each other and laughed. He then offered us some wine. I saw a plastic motel room cup with a tiny bit left so he must have already had a glass. I said, "sure why not, one glass wouldn't hurt" he then unwrapped two plastic motel cups and handed each of us one. He then opened the room's fridge and pulled out the bottle pouring each of us a cup of wine.

He rolled up his sleeves of his dress shirt sat down in the chair across from us. The music coming from the television was low enough that it didn't drown out our small talk but still kept us entertained. While slowly sipping on the wine he asked about the town he was in, whether there was anything fun to do around here and how it was not at all like the big city of Cheyenne. During all this wine sipping and small talk, I couldn't help but see him check both me and you out through the corner of my eye. I would see him look at you trying to get you to make eye contact with him then I would catch him checking out my legs. Of course little did he know I was checking him out too. I was checking out his big strong hands each time he raised his cup to his mouth and then I’d glance at his crotch since he was practically sitting with his legs wide open. Probably doing it purposely. I could tell he had a nice package since the bulge looked big. I just about finished my cup of wine, you were only halfway done and he finished what was probably his second cup. He then got the wine bottle and filled my cup again as well as his. He then said how a weeks’ worth of sitting through those meetings really made his neck stiff and that what he could really use is a good massage. Without missing a beat you chimed out and said, "Kristen here gives great massages" that just made me wonder what you were thinking about all this time and what was going through your mind when I caught you checking him out too.

I guess I was pretty much obligated at that point. But since the wines was kicking in and since you pretty much said, go for it, I got up and walked behind the chair he was sitting in. I put both hands in his shoulders and gently massaged around the back of his neck. I could see his eyes closed and could tell he was enjoying it. He would move his head around as to tell me the spots to hit. He had very hard shoulders and could tell he must work out. I would look over at you and all you were doing was smiling as if you were enjoying it too. He then told you to give it a try. You were hesitant at first but then I told you if I have to you have to. You got up and stood next to me rubbing his shoulders. He then said, “you know girls, I'm really enjoying this, you don't mind if I slip into something more comfortable" I then said no not at all. He then finished his third cup of wine and went into the bathroom.

While in the bathroom we heard the water running. I think he was taking a shower. After a few minutes the water stopped. A few minutes after that he came back out. He was just wearing a towel and his hair was just a little wet. I couldn't help but notice how good looking he really was. Maybe it was the wine but his body was fine. He had a strong looking chest and nice abs. His legs were also strong looking. He wasn't overly muscled just enough to be hot and sexy. He turned to the side and showed the nice shape of his round ass. Kristen was getting so turned on. I looked towards you and you were also staring just as I was. He then asked if we'd like to continue his massage. Before anything more was about to happen. I told him that we have a confession to make. I then told him,” I'm not really a woman. I'm a crossdressing transvestite.” Thinking he was going to be in so much shock that he would probably kick my ass and chase us both out a fast as possible, he says, “I knew that, I knew when I saw you posing in the parking lot." I said you did? He said, "Yes, I have no problem with it, I'm attracted to crossdressers and transsexuals too, and you are very sexy" at that time I blushed but felt so relieved. He then said, “now how about finishing that massage". I guess his calmness with it kind of calmed you down, maybe the wine helped too. You seemed a little more relaxed and interested in what was going to happen next. Still wrapped in his towel he laid face down on the bed. He smelled so good, he must have sprayed on some cologne or it could have been the soap he used. He asked you to take off your pants and shirt and get comfortable. He asked me the same thing but didn't want to mess my look up and felt more comfortable with my girlie clothes on. You stripped down to just your panties and bra and we both got on the bed with him and started rubbing his back. I don't know if what we were doing would be considered a massage but he was enjoying it. He would say things like, mmm....that feels good, and yes, that's it. I think we took turns rubbing his back and the back of his tight legs. Neither one of us touching his butt, at least not yet.

At that time Kristen couldn't help her; she slowly reached under his towel and felt his hard ass. She then straddled his legs using both hands on each cheek. Every time her hands would get close to his cock she could feel the heat from that area. It was getting hard not to move the towel off his butt. At this point you backed off just watching Kristen getting so excited and having so much fun. While having both hands on his cheeks massaging his ass underneath the towel I started to lean over every once in a while to kiss his back slowly moving my lips lower and lower. All the time hearing him lightly Moan with mmm's and ahh's.

Well to my surprise. He started to get up. Still wrapped in his towel he stood in front of me as I sat on the foot of the bed. You went to sit back on the chair still close to us and still in your bra and panties. He said, I have something for you Kristen" "I know what you're trying to do" “you’re trying to show your girlfriend that your crossdressing sissy ass is brave enough to go all the way with a real man.” “You probably thought she would back off or you were going to be too nervous and scared " "but hey you made it this far, no turning back for you now" " I tell you what, do you think I'm attractive?" Yes, I said, he then said, "what, I didn't hear you" I then said, "Yes sir" he said "that's the good girl" "sir" "I like that". He then said that that he would let me do whatever I wanted to do, what I’ve been longing to do for so long and told you that you could watch or join in. he looked straight at me and said, "good job on your dressing tonight, you look good enough to fuck". I looked down and could see his towel slowly rise up. It was rising up by itself or so it seemed. I looked closer and could tell that his boner was nice. I could tell it was long and big. I didn't know what to do or say next, but something else came over me as if I was in a trance.

So you want to see what I have for you? Yes sir I shakenly said. Something you've been craving for a long time. Something you can't stop thinking about every time you’re dressed? And what's that sir, I exclaimed. This, he said, as he unwrapped his towel.
I then seen the most gorgeous looking cock I've ever seen. It was so big and hard. So good looking. My mouth started to water. It wasn't small at all and just the right size. His pubic hair was almost nonexistent I could tell he took care of himself with even the little things. I was close enough to feel the heat from his gorgeous manhood it even smelled fresh. All I did was just stare and gulp. He then said, "Ok Kristen, show your girlfriend what you like. Show her how much of a girl you could really be. If you really want to be a girl, then your slutty ass will have to do girl things. “so show her, show me you sexy bitch" I then couldn't help myself. Since I was sitting down with it right in front of me I reached around and grabbed his tight ass with both hands to slowly bring that nice cock closer to my pink shaded lips. As it got to them I opened my mouth and saliva drooled a little off the corner. It was then that I tasted him. I slowly put my mouth around his warm head trying to get it slowly in further. I started sucking it and moving my tongue around slowly wanting to taste every inch. I knew I didn't know how to give a blowjob but tried to remember some porn videos where I’ve seen it done. Every once in a while I'd grab his firm ass each time trying to put him further in my mouth. I knew I would never get all of it in my mouth. It was just too big and slightly thick. And his big balls would bounce back and forth too. But oh how good he tasted. I think I was doing good enough because I would hear him say that's it Kristen suck my cock, you know you want it don't you sissy bitch. I mumbled out yes sir I do sir but you couldn't hear what I was saying because my mouth was full of his delicious cock. Meanwhile I felt myself get so hard. My panties that were holding my sissy clit in were starting to ache. It was like a full pitch tent. I went to reach down to pull it out of captivity when he told me, don't even think about it. Don't touch your clit you little whore. He then looked at you and told you to reach over and release it from my panties. You then leaned over and reached your hand under my skirt pulling my panties aside. "Boing" my sissy clit was free. I felt even more relaxed. He then looked at you and told you, don't just sit there. I want you to play with yourself while you watch your sissy friend here mouth fuck me. You then nervously reached one hand under your panties touching your wet pussy and the other hand under your bra playing with your hard nipples. I looked over briefly saying to myself; "glad I'm not the only one enjoying this"

I still couldn't help but want more. While still sucking him I slowly stroked his long shaft in and out of my mouth. I massaged and cupped his big soft balls that felt so good in the palm of my hands. Still watching you look at what was happening then closing your eyes every once in a while fingering yourself. This hot sexy man would look down at me watching his cock get sucked then look at you playing with yourself. He then told you to get up and get behind him so you could have a better view of what I was doing. You stood behind him just holding him around his waist while you looked at me taking him in and out of my mouth. Every once in a while he would reach around with one of his arms and play with your pussy while his other hand was on the back of my head pushing me on him. He then told us to stop. He told me to get up and of course I replied with just a "yes sir" he then laid on his back on the bed. He put a pillow under his head. Again I couldn't help but to admire his big cock sticking straight up and his rock hard abs flexed. His strong legs spread slightly apart. He then told us that both of us had to suck his cock together. At that time we both got on the bed, one of us on each side of his hips. I went first as I grabbed his hard shaft and slowly put him back in my mouth again only getting like half of it in, after a few times I raised my head up and gave you a turn. You nervously went down on him slowly licking the head of his dick and putting it in your mouth. I saw his hands grabbing the bed, balling up the bed spread with his fists. My sissy clit got so hard listening to him moan and even harder watching you actually sucking another guy’s cock.

At that time he told us to stop again. I couldn't imagine what he had in store for us next. By this time my clitty was dripping a little from sucking and tasting his gorgeous cock. I still couldn't believe how hard he still was. He then said are you guys getting what you came here for, not even knowing it would lead to all this but so much enjoying Kristen getting treated like the sissy slut she is, all I said like instinct was "yes sir" . Do you want more? "Yes sir" say "please" he said. I instinctively said “please sir, give me more". He then said remember Kristen when I told you that you looked good enough to fuck? I quickly said "yes sir" he said well guess what. It’s time to get fucked. Straddle me. "But" I said hesitantly, no buts show your little girlfriend here that you're ready to take it in the ass. Remember you want to be girl. You feel like a girl when dressed like one, time to pay your dues. Now ride me. "Yes sir" you were still sitting beside him when I nervously straddled both his legs. I sat in front of him with my hard sissy clit touching his big good looking man sausage. He then reached down and grabbed both of our cocks in his strong hand and stroked both of them together. I loved the way his silkiness pressed against mine. The warmness of our two cocks rubbing against each other was so hot. I began to rock back and forth with the rhythm of his strokes. I felt my boi pussy opening up too with each rock back and forth I felt my thong rub in and out of my crack. He then said, "Are you ready Kristen? “I said yes, I want it so bad. I want to feel your hard cock in my ass. Please give it to me. Fuck my ass, please fuck me now sir"

He then reached around and forcefully grabbed both my ass cheeks from under my skirt. I could tell he was strong by the way he easily brought me further on top of him. I was now sitting with his cock behind my ass cheeks. He then told you to get that bottle of lube that he had in the front pocket of his suitcase. You then went over and got it. He then told you to squirt some in your hand and rub it on his cock. He told you to stay close cuz he wants you to do something else in a couple of minutes. He then said to me "mount me slut" he lifted my ass up higher while my knees remained straddled on the side of his legs. He said; now slowly sit on my cock. I slowly sat down. I could feel his hard head trying to penetrate my virgin ass pussy. I felt the coldness of the lube and the warmness of his cock at the same time. He said again that I had to go slow so it doesn't hurt. Again I couldn't help it. Kristen wanted to get fucked and this handsome stud was being gentle yet confident. I began to shake and my legs began to tremble as I sat further and further down on his cock. It was somewhat painful but the pleaser was intense. I couldn't help but moan with pleasure. I moaned, "Yes sir, fuck me sir. It feels so good sir. I love the way your big cock feels in my ass sir" I grabbed his hard muscular chest with both hand and tried to go up and down. His cock felt so good in my ass I couldn't get it all in but making the best of it, I rocked back and forth feeling the pleasure with each further entry. I had tears in my eyes from the pain and from the pleasure. He encouraged my every move with “that's it Kristen that's it slut, fuck that cock, you know you want it.” He then told you it was your turn to get wet. He told you to sit on his face I want to lick your pussy. You took off your panties and slowly mounted his face. I saw his tongue start licking you as you sat just above his face I had seen your eyes close with pleasure too. That just made me move faster on his cock.

Kristen was enjoying it so much. Both of us were with this complete stranger, yet felt natural at what we were doing. He finally said, wait I need to get up. I un- mounted his cock and you his face. He got up off the bed and told me,” wait I'm not done with you Kristen.” He then told me to stay on the bed but this time "face down, ass up" that made me even wet. I kneeled on the foot of the bed while he re-lubed his still hard monster cock. I put my ass up and face down. I felt him push my skirt over my ass and move my thong aside. Then felt his meaty man-ness enter me again. It felt even better than before. He told me, now you’re really going to get fucked like a woman" he started pumping his cock in and out of my ass pussy, first slow then fast. I felt my sissy clit just dripping I think I must of came so he must of been hitting the right spot. All I remember was me telling him more and more that I loved the way he was fucking me and how good it felt.

Then it started to happen. I could feel his cock getting warmer. It also felt like it was getting thicker and fuller. He was pounding me so hard that I didn't even realize he was all the way in. I never thought I'd be able to take all of his manhood inside me but the excitement and unbelievable feeling of ecstasy must have bypassed that doubt. His pounding felt so good his balls slapping my ass and Kristen, with her sissygasm, felt so much more like a woman. Her womanhood must have had her instinct at that point because she felt him ready for him to have his orgasm. She must have sensed it was close. She told him, give it to me sir, cum in me, I want your cum in me sir" he then tightly grabbed my hips squeezing very hard and let out an "aaahh" I felt his hot juice spray inside me. And there’s more where that came from. He kept squeezing my hips and started to pump his hips into me. Every pump of his hips I felt more and more of his hot man seed ooze inside me. He must have been pent up for some time. Poor married guy. I even had more of mine dripping out of my cock. There was nothing but a big wet spot on the bed cover below me. I looked over at you and it also looked as if you just came. You just smiled and said, "Good job Kristen" he then slowly pulled out his cock out of my boi pussy and it was finally getting soft. He then said, "Yeah, good job Kristen, you're a good girl"

After that he said, “well I'm kind of beat, it's been a long day, I better get some rest.” Getting the hint you got your clothes back on and I straightened up my skirt and fixed my wig. He put on a pair of sleep pants and gave us both a hug. He said thanks for the good time and I said same to you sir, as we both went giggling out the door. While walking back to our room I was moving a little bow legged. I guess Kristen really did get fucked good. She was feeling a little sore and could feel a lot of cum dripping down her stockings. We got to the room and it was already past midnight we both crashed on the bed. I didn't even clean up or change out of my clothes. You dozed off right away and me shortly after. I guess we both were beat. Both with smiles on our faces.

But just when I thought it was over. I heard a soft knock on the door. I thought to myself, what now, someone really did crash into my truck, I tried waking you up but you were in deep sleep, I looked at the clock and it was 4:00 am. Not even remembering I was still dressed I quietly went to the door. I peeked through the peep hole and seen Mr. hot stuff standing there. Thinking to myself we must have left something in his room last night. I slowly opened the door and he was wearing his sleep pants still and a t shirt. I told him you were asleep and asked what he wanted. He said he'll be getting ready to leave and just wanted to say good bye. He thanked us again for the good time. I said ok have a safe trip drive safe. When I was just about to close the door I looked at myself through the full length mirror by the bathroom. I realized I was still dressed and still didn't look half bad. I looked back at him as he was turning to walk away. For some reason Kristen was still inside me. She reached over and grabbed him and pulled him back in the room. I put my finger up to my mouth and told him "shhh" we have to be quiet, she's still sleeping. I grabbed his hand and walked him into the bathroom I left the bathroom light off and the door slightly open to have a little light from the television. I sat on the edge of the tub while he stood up. Both of us not saying a word. I started rubbing his cock through his sleep pants getting him nice and hard. I pulled up his t shirt and started kissing his abs kissing further and further down. When his gorgeous big hard cock was at full attention I slowly pulled his sleep pants down and put him in my mouth. I grabbed both sides of his hips pulling his cock in and out of my mouth. I could tell he wanted to moan but we were so quiet as to not make any noise. I swirled my tongue around the head of his cock while it was inside of my mouth. Again it was so delicious and my clitty was getting hard again. I would jack him off with my hand strokes and put him back in my mouth. I pulled his cock out and ran my tongue up and down his shaft. I went lower down his shaft and licked his balls for a while. I could tell he was enjoying it. His heavy breathing was turning me on too. I then stroked his cock in and out of my mouth again. His breathing became harder and I grabbed both his ass cheeks. I put him my mouth as far as I was able too without gagging. I felt him get hot and swell more in my mouth. I knew he was ready. I squeezed tight on his ass cheeks as he grabbed the back of my head at the same time he let out a breath I felt his cum shoot into the back of my throat. I instinctively swallowed his cum. It tasted warm and sweet. I then got up with my panties dripping again. He pulled up his pants and pulled down his shirt he gave me one last hug and I told him goodbye, thanks for everything, he then said, thank you ma'am. How ironic. I quietly closed the door and went back to lie down.
Well the sun finally came out and after sleeping in a bit I took a shower and took off my makeup. You got ready to as I put my Kristen attire away. We both left knowing we had such a pleasurable night. I never told you about him coming back to the room and how I sucked and swallowed that handsome stranger. Maybe it was for the best. But I’ll always be willing to do it again sometime.