The Hitchhiker free porn video

The hitchhiker - Part 1 I had recently broken up with my girlfriend and with a bit of a midlife crisis decided it was time to travel across the country to start a new life. I had sold most of my stuff and no fixed agenda so I thought I would make a bit of a tour of it. I decided that it would be best if I had a travelling companion so I put an advertisement into the local paper and on the local community notice board. I had 3 replies from people who were keen to cruise there way across the country over a week or 2 weeks, depending on how long it took. I decided that it would be best to interview them, that way I would have a better idea if we would get on. The first was a girl, mid 20s. She was a bit overweight and had a very annoying laugh. The second was a guy in his mid 20s also. He was a computer type and was going to a job so could only spend a week. The third was a real surprise. She was in her mid 30's, was very attractive and had dark skin, dark eyes long legs and very large breasts. She was going to catch up with some old friends and thought a trip would be fun for however long it took. The decision was made there and then and we arranged for the pick up place - maybe this was going to be more fun than I expected! On the first day I arrived and met Cleo at the designated place. I arrived in my BMW and could see that she was impressed at my vehicle. She looked super sexy. She was wearing a tight denim mini skirt which made her legs look longer than when we met for the interview and a tight white T-shirt. I could see her breasts clearly through it so she either had no bra on or it was a T shirt bra and they looked even bigger and more inviting. She had on red low heels. Her hair was tied back in a ponytail which enhanced her sexy eyes. I could almost feel myself go hard at the thought of driving for a few weeks in the car with her and was immediately attracted to her. We headed off and spent the day talking to each other. She had lived in our town for a couple of years and before that had been in a couple of towns. She didn't have a boyfriend as she found "they held her back on having fun" and she hadn't had one for years. She liked being able to have fun where and when she wanted. For recreation she liked rollerblading as it helped shaped her legs and kept her tanned. She also loved looking at the hunks while she was doing it. She believed that everyone made their own luck, and that you should always make the most of the situation - like this one! I certainly got the feeling she licked me as we talked and thought this could be good fun. We grabbed some drive through food on the way into the town we were going to stay in and as we were getting on OK decided to share a room with separate beds to save the cost. We got to the room to and Cleo made a drink of special herb tea to help us sleep after driving for the day. We were both very civilised and that night I went to sleep feeling pretty damn good about the sexy chick who would be in the car with me over the next couple of weeks. That night I had some great dreams about Cleo and having hot steamy sex with her. I woke up with a raging hard on and to Cleo having made another special herb tea to help with the drive. I went for a quick jog while she had her shower and when I got back was again stunned at her sexy appearance. She was wearing her mini skirt again and had on a hot pink tank top that I could clearly see how perfect her big breasts were. She had on black low heels today and her hair was tied in two pig tails either side of her head. I was feeling pretty horny and thought about jerking off when I had my shower but decided to wait - I was pretty sure that the next few days I would get to have sex with her. While I had my shower she made a couple more drinks for the day while we were driving, a sort of orange drink that tasted a bit strange but was quite addictive. I had pretty much finished mine by mid morning and so she offered to make me another. We had another great day, laughing and telling stories. She told me about her best holiday which was when she went away with a guy to a tropical island and they had such fun. I told her about the time I went on a ski holiday with a girl and the weather was not so great so we spent our time in the lodge by the fire 'enjoying' each other. We continued to get more and more explicit with our stories and I was getting hornier and hornier. I had a couple of top ups of Cleos drink through the day - it really was good. As the previous night we decided to get drive through and share a room with separate beds. I really wanted to jump into hers but decided that I would wait until she made the first move. After dinner she slipped into her night wear which was a silky short nightgown that was super tight on her big breasts. She made her special relaxing tea again and as she did jiggled and really showed off her body. I was so horny for her but again w went to sleep in separate beds. During the night I had the dreams of sex again. They were slightly different in that there was a couple of other guys joining in and they were doing me as well as Cleo. My cock was also much bigger then normal, instead of 6 inches it was at least 10. I woke up with a rock hard cock again and Cleo had made me her special tea and left it beside the bed and was just finishing a shower. She came out wearing even sexier clothes. Tight high cut white hot pants that showed half her sexy but cheeks. I could see the white lace G-String she was wearing under them clearly. She had a short tight pink tank top that accentuated her breasts and exposed her flat tummy and belly button. She was wearing little ankle socks and sports shoes and her hair was tied back in a pony tail again. I quickly had my shower and we hit the road. Cleo had made her drink again and I seemed to drink even more of it this day. We continued to talk and open up to each other and I continued to check out her body which was so hot and with what she was wearing left nothing to the imagination, resulting in a couple of times having those awkward moments where we both looked at each other and wanted to say something but didn't and just chuckled it off. As it got later in the day and we had been talking about relationships she started talking about a guy she had seen for a few months who was very experimental. She said how he enjoyed wearing her underwear and other clothes and how much she loved it and it turned her on. She asked if I had ever tried it. I was a bit embarrassed and said "No Way" but she countered with a "You should try it, you might be surprised". After this we also talked about how we would want to look if I was a girl and she was a guy. I indicated that I would want to look like her - very sexy body, long legs, ample breasts, sexy face and be really into sex. She said she would want to be pretty much like me, good physique, strong features and keen to experiment. That night we decided to have dinner in the hotel restaurant. We went to the room and quickly changed, me into jeans and a shirt and her into a mid thigh length turquoise silk cocktail dress that fit like a glove. She had white high heels on and her hair was loose and you could see the great texture in it - she looked absolutely stunning and I thought I might have cum in my pants right there! As we entered the restaurant most the guys checked her out and I felt very proud of the fact that she was with me. We ordered a couple of drinks as we decided what we were going to eat. I was thirsty and quickly finished mine while Cleo had only had a little of hers. I had to go to the bathroom so she said she would order another for me. When I got back to the table she had got it already and I also drank this one (it was a triple shot and tasted a bit different but I figured she had selected different vodka) and when our meal arrived I ordered another. (I didn't know that Cleo had asked for the bar tender to make the next one a triple also). Cleo continued to drink hers slowly so that at the end of dinner she had had one Vodka and I had had 3 of which 2 were triple shots and 1 had a strange taste and by the time we had finished dinner I was feeling very lucid and light headed and besotted by the stunning Cleo sitting opposite me and teasing me by bending forward and showing her ample E cup breasts and making sexy actions and remarks. We headed back to the room and I wanted to have a quick shower to cool off. Cleo said to make it quick as she also wanted one and when I had finished my shower I exited the room wearing the hotel bath robe. Cleo had made a couple more drinks (hers was straight tonic while mine was a quadruple shot) and she quickly went into the bathroom after me and had her shower. Lying on her bed was lots of lingerie, as if she had picked up her bag and just emptied it on the bed. Given how horny and lucid I was and the conversation we had had earlier in the day, I wanted to look at it closer. I picked up a couple of items, lace and silk panties, lace stockings, suspenders, a bra and was looking at them when I heard Cleo ask "How do you like the feel of my lingerie"? I was surprised to be caught out like that. I thought she was having a shower as I could still hear it running. I turned around and she was standing there with just her panties. No cocktail dress, no bra, no shoes, just panties and wonderful big breasts. What the hell I thought, they did feel pretty good in my hands. "Ummmm, it feels sexy" "Would you like me to dress you up, it would turn me on and I know you would love the feeling"? As she finished saying that she reached up and gently rubbed the side of my face. Her touching me and standing there almost naked along with my head space which made my cock go from being semi firm to properly hard and continued to say. "Don't you think it would be fun to try something new"? And as she said this her other hand started to rub against my hard cock through the bath robe. I could not resist her offer and almost reluctantly said "OK, lets have fun, I want to try it" A big smile came across her face and I could tell she was really looking forward to this. At the same time I grabbed the drink and drank it all knowing it would help to keep me lucid. (What I didn't know is that this and the travel drinks of the last few days, including the teas had special chemicals in them which were changing me, but more on that later). "Well, the first thing you need to do is take off the bath robe, I need to know what I have to work with" she said as she untied the bathrobe and peeled it off my shoulders so it fell to the floor. With that she rubbed the back of her hand over my thigh and butt and commented on my nice strong legs and strong sexy butt and how good they will look in lingerie. She also rubbed my chest and commented on my hairy chest, saying that it was a shame to hide such a good chest with so much hair. "Now, the first thing is to put on your suspenders and stockings. Now which ones for you? I know, these ones." As she said this she this she reached onto the bed and picked a pair of black lace suspenders with red trim. She wrapped it around my waist and then clipped it up. Then she grabbed some black fishnet stockings with small 'nets' and slid them up my legs and clipped them on. They felt really, really good on my legs - in fact I was quite surprised at how good they felt. "How does that feel baby" she asked "Really good - surprisingly good actually" "See, I knew you would like it. Now panties and bra..." She reached over and got a pair of red lace G-string panties with a black bow on the front. She slid these up my legs and over my cock. She bent my cock down to 'bury' it in the panties and pulled my ass cheeks apart to ensure the G went right in my crack. Then she pulled them up a bit and I could feel the string on my ass and the lace on my cock. She than grabbed a matching bra, red with a black bow in the middle. It was one of her bras so was E cup. She stood back and said "we will have to fill the big gap in that bra" and reached into her bag and pulled out what looked like 2 balloons, went over to the sink and filled them with water. Then she came back with what looked like two big breasts and placed them in the bra. Wow, I was having amazing sensations (no doubt spurred on by the drinks and chemicals). "Ohhh you look sexy baby, lets get some accessories and then we can do your make up". She had a pair of red high heels that went with the panties and bra and I put them on. Then she told me to sit down while she did my make up. She then applied make up to my face, eye liner, lashes, foundation, lips and because she was bending over in front of me her big breasts were swaying and jiggling - which turned me on even more. The last thing she did was put a platinum blonde wig on me with a straight cut fringe. "There, gosh you look hot. Do you want to check yourself out in the mirror"? I did and got up and walked over to the full length mirror. The panties and stockings felt great as I walked and the big breasts moved like real ones, all adding to my sensations. "Wow, I don't even recognise myself - that's amazing. I look like a real sexy girl." I was blown away. My lips were prefect Red, and around my blue eyes was dark and sexy and the lingerie looked wonderful (and felt amazing) "Do you like what I have done"? "That's amazing - I cant believe it" "Why don't you do a sexy dance for me and turn me on" she said as she sat down on my bed. "I was in the swing of things and started to do what I thought was a 'sexy dance', swinging my hips, arms above my head, turning around and bending over in front of her. I did this for about 5 minutes when she said "Come over here, I need to do some adjustments for you. Do your sexiest walk and ask me how sexy I think you are in your best tranny voice" I slowly walked over to her swinging my hips as much as I could with my hands on my hips. In my best imagined tranny voice I said "Do you like what you see baby, do you think I'm sexy. Do you think I'm hot" When I got to her she replied "Mmmmm very sexy baby. I think we are going to have a lot of fun on this trip" She reached around and wiggled the suspender into a better position and then grabbed the waist of my G-string and pulled it up at the back so it went further into my crack. Then she reached into the front of the panties and said "I think this needs some adjustment" as soon as she touched my cock it became harder (it was semi hard) and she said "I can see we are going to have to relieve this to achieve a better look" With that she pulled the front of the panties aside and started to stroke me with both hands and then reached forward and licked my cock from the bottom to the top. It made me shudder with pleasure and she did it again and then opened her mouth and took my cock into her mouth and swirled her tongue around the head. It felt amazing and as I looked down I could see the sexiest chick I had ever met sucking me. It was only a few minutes before I was ready to shoot my load. She could tell and took my cock out of her mouth and started to pump it hard and suddenly I was shooting my load all over her big juicy tits. I felt so relieved to have finally emptied the build up I had in my testes from the last couple of days. She took my cock and tucked it back into the panties and lay back on the bed and said "Come and lick your cum of my tits baby before it makes a mess". I wasn't sure about this - it seemed a bit weird. "Come on baby, it tastes yummy - if you want me to suck it out of you next time then you have to taste it first" That was enough of an incentive for me. I climbed on the bed and bent down and started licking my cum off her tits. It tasted better than I thought and within a few minutes it was all gone. I wanted to get into more action and started to stroke her big breasts and moved my hand down towards her crotch but Cleo was not going to have this. She grabbed my hand and told me it was bed time and, with a wink of her eye and a cheeky smile, that I would need all the rest I could get. This just made me more compliant so I climbed off the bed. As I did she said "If you are a good girl and sleep in what you have on, I'll suck you again in the morning" I was disappointed that I was not going to have any more action but felt content that in the morning I might get the chance. "You can take the shoes off but nothing else" "Cant I take these massive tits out"? I asked "Baby, do I take mine out at night? No, only the shoes - that is if you want me to suck you again. Do you"? "Ohhh yeah, I want more too. Can we do more" "Good things happen to those who are patient - all in due course" She made a cup of her tea again for us and then went into the bathroom and changed into her short night gown again and we went to sleep. I went to sleep feeling very sexy in the lingerie and happy & horny - excited about what tomorrow would bring. That night I had even crazier dreams. In these I was wearing lingerie, but I had real tits and was being fucked by about 10 guys all taking turns at fucking me and me sucking them. Cleo was also being fucked by them and we were both having a great time, in fact I was loving it. This is where the special drinks started to kick in (I discovered this later). The way Cleos special formula that she had been secretly giving me worked was this. As soon as I drank my own cum after I had started taking the drink caused my internal genetics to start to change. It was like a time bomb in that the longer the gap from when I first started 'taking' it until the time that I first tasted my own cum after determined the potency of it. The longer the period in between first drink and drinking my cum, the stronger the potency. Usually the person would cum and drink it the first day they had it because they were so horny (under Cleos guidance), but for me it had been 3 days which meant it had 3 times the normal potency and would have 3 times the impact. By swallowing my cum I had just started the reaction to occur and the impact of it started. The special formula had a simple outcome - to alter the person who was taking it into a very sexy and extremely horny shemale. The more potent the formula, the hornier and the 'sexier' the shemale would be. Continuing to take the drink, and my cum would also enhance the effects of it, compounding the impact (hornier and sexier). Another factor was determined by the generic genetics of the person. For some it would have little impact, for others their genetics were susceptible to the change and thus had a bigger impact. Cleo didn't know that my genetics were prime for this or she probably would have sucked me off earlier and I think even she was surprised at the outcome. The dreams were all part of the changing going on inside me - my alteration was starting to take effect. I woke up in the night and noticed that I had cum in my panties - the dreams were too much. I got up to change but there were no panties there so I thought I would try to clean up - I wanted that suck from Cleo. She must have heard me and asked what I was doing. "You made me so horny I've cum in my panties and wanted to change. Do you have another pair" She got up and said 'Ohhh baby, I'll give you another pair to wear. Since you enjoyed licking your cum off my tits earlier you just have to lick up all your cum off the old panties first". I didn't even think about it - I did enjoy tasting cum for the fist time so I stepped out of my panties and started to lick up my cum. When I had finished she gave me a new pair which I put on and went back to sleep. I continued to have crazy dreams but did not shoot my load again. In the morning I woke up to the normal cup of tea and the driving drink already made for the day. Cleo was up and dressed and on her bed was some clothing for the day. I got up and headed to the bathroom to have a shower. Once I had cleaned myself I dried myself off. I noticed that I looked a bit different but couldn't figure it out. Then I realised that I didn't have any body hair - around my cock, on my legs, on my arms - there was no hair. I stepped out to tell Cleo that all my body hair was gone. She looked so sexy. She had a tiny pair of denim hotpants on, a tight white T-shirt that started above her belly button and only just covered her huge breasts with no bra underneath, meaning you could clearly see her nipples through it. Her shoes were a pair of red semi high heels. She allowed me to check her out and then turned around and you could see the G-string from behind that was above the top of the hotpants. I thought "Wow, how lucky am I"! Then I told her that I had no body hair. She smiled and said "Ohh that might be a reaction to the herbal tea. Part of the cleansing properties may mean that your body wants new hair - like a fresh start. Anyway, I think it is sexy and it turns me on." It sounded feasible so I believed her. I went over to my bag to put on my clothes for the day, but I couldn't find my bag and asked if she had seen it. She said "I have already put your clothes for the day on the bed" I looked on the bed and there were my jeans, a T-shirt and a sweater. Beside them was a selection of lingerie. As I looked at it she sashayed up to me and said 'Well, since you liked the way the lingerie felt so much last night, I thought you would want to wear it again today under your normal clothes - no one will know. And it turns me on to know that you have this on under your clothes so if you want me to suck you again, you will need to wear what's on my bed". "But where are my clothes in case"? "I have taken them and they are in the car, but you wont need it, unless you don't want sex any more"? There was no debate, I really wanted sex with her! I went over to the bed and started to sort through the lingerie. I thought I would put it on in the same order as we had the night before. I grabbed the suspender to put that on first. It was white lace and had a pretty little silver bow on the front. Then I put on the stockings. These were also white and had a fine fishnet on them. I slid them up my legs. They felt wonderful and I immediately felt my cock twinge with excitement. Next I got the panties and put them on. They were a pair of bright red, lace fronted G-string. The challenge was the pouch for my cock was small, and the lace felt great - Cleo came over to help and kept on trying to force it in until she said "We will have to deal with that before we head out for the day"! Next was the bra, also bright red lace and B cup. Cleo said "No breasts today baby so you don't feel too conscious about wearing the bra, but we can again tonight - if you are good!" It felt good just to have it on. I was about to go and put on my jeans when she said "You look so hot baby, come and let me suck you so your cock behaves in those sexy panties" I stepped over to her and she lowered my panties and started to lick my cock. She did long strokes from the bottom to the head and then swirled her tongue around. Then she took it in her mouth and forced it into her throat. She continued to do this and it felt so good that within a few minutes I was ready to cum. She knew that I was close and started to suck as hard as she could. Then I was cuming in her mouth as she sucked it back - but she didn't drink it. She stood up with her mouth full of cum and held my head and then gave me a big kiss on the mouth, forcing my cum from her mouth into mine. When she finished she stepped away and said "Swallow it baby, it's yours"! I did as I was told - Cleo seemed to have absolute control over me - if she wanted me to do something I would have. She tucked my now spend soft cock into the panties and said that I could get dressed in the rest now.. We headed to the car to continue our journey. It felt really crazy walking to the car in the under clothes I had on, but it also felt great. That day we talked lots about all sorts of things. Now that the barriers were truly removed we were able to get a bit more personal. She really started talking about wearing lingerie and what life was like as a very sexy girl. We also talked about crazy sexual experiments we had done. She mentioned her boyfriend who liked wearing lingerie and that one time she had slid a finger up his ass and if had I ever tried it. Of course my response was no and once again she said "based on the fact that he shot the biggest load of cum in my mouth when I did I think you should try it - so you can cum in my mouth!" We talked more about this and favourite scenes from porn movies - I told her one of mine was from a movie called 'Anal Thunder' where a guy with a big cock absolutely pounds a very sexy girls ass as she screams in pleasure and pain at the same time. When he pulled out her ass was wide open and looked so inviting. I could tell she liked this so we talked more about anal sex and I asked her if she had ever tried it, to which she said "Yes, a few times and it felt great! In fact it is my favourite way of having sex." This really got me excited about that evening. We got to our destination for the day and found a hotel that looked good. They only had 1 room left that had a king sized double bed. I looked at Cleo and was about to say we better go else where when she said "That is perfect, we'll take it". Maybe tonight I could go all the way with her! We got to the room and decided to have a few drinks before we went out for dinner, vodka and tonic (same as the previous night hers was tonic, mine was a triple). After a few drinks she came over to me and gently stroked my leg and said "Do you want to go further than we did last night?" I nodded yes. "How much do you?" "I really want to" "OK you sexy thing, I want to dress you up like I did last night for our dinner, and then when we get back we can have some real fun. What do you think?" "I'm not sure, going into public dressed like a girl is a bit strange" "Baby, the way you looked last night, no one will know. Plus, we'll go somewhere where we aren't noticed much, I know a few places in this town, and it will really turn me on and get me horny" "Are you sure I won't be noticed" "You'll look great - I promise, and I know you'll love the excitement". "OK then, for a bit of fun" "Ohhh you are so much fun - lets get started" She told me to take off my 'man' clothes and the little bra, which was replaced by the same E cup bra and the huge false breasts I had worn the night before. Then she pulled out of her bag a bright blue tube dress that would be very tight (it was at least one size too small). I put it over my head, put my arms in the sleeves and pulled it over the huge false tits and down as far as it would go. It was very tight and didn't quite go past the top of my stockings revealing a bit of bare leg. I was glad my leg hair was all gone! If I sat down you would see up the dress and if I bent over you would be able to see my ass and the G-string in my crack. It also made my false tits look really big because it was so tight. Then she grabbed some shoes, these were bright red high heels and the colour clash made for a very sexy combination. Then we went to the mirror to complete the make up - the same as the night before with the foundation, eye liner, lipstick, painted finger nails etc. Last was the blonde wig from the night before. During this process I had drunk another tripple Vodka and was really getting into it. "OK you sexy slut, ready for action"! I stood up and looked in the mirror - a very sexy and slutty girl was looking back at me with huge juicy tits. She then quickly put on the same sexy turquoise dress from the previous evening and white high heel shoes. We went to the lobby and got in a cab. She asked the driver to go to an area place she knew. We exited the cab and had a bit of a walk to get to the restaurant. It was tricky walking in the high heels with such big tits - my balance was completely different to what I was used to. We entered the place and I noticed it was a combination of a bar and a restaurant. There were people eating so we asked for a table. They told us it would be about 10 minutes and we should wait at the bar. We headed into the bar and I was blown away by how many guys were checking us out as we headed to a table. I felt pretty good to be getting checked out so much - Cleo had done a great job with dressing me and making me up. She said "I'll order some drinks" and headed over to the bar and came back with a couple more Vodkas. I noticed the guys watching her and how she swayed her hips to look even sexier than she did. As I sat there I felt quite nervous - what if a guy came up and started talking to me? I raised this with Cleo when she got back, what should I say, what is my name, etc. We were chatting about this and trying to decide a name. She said she had always thought Xanthe was a mysterious and sexy name and that it suited me so we agreed that I would be Xanthe. We had just finished chatting about that and only been there about 5 minutes when our table was ready so Cleo said "Ok, drink up, we can't enter the restaurant with drinks" I drunk down the Vodka and was starting to get a real glow on (Cleo only had tonic). We were seated at a quiet table and quickly ordered our dinner. During dinner we continued to chat about 'my story' which also became 'our story'. Everything was normal and true except that I was Xanthe, and had just broken up with my boyfriend and Cleo was taking me on a road trip for a break. For a job I was a shop assistant at a lingerie shop. Other than that we made everything the same but Cleo wanted me to tell her in a sexy female voice to practice. We had several more drinks of Vodka which Cleo ordered as "the same again for me and for her" We finished our dinner and as we had a late night before and decided headed back to the hotel. Passing through the bar, which had become more full, the conversation just about stopped as 2 big breasted hot chicks sashayed their way through. I was a bit drunk but that helped me to act like a sexy chick and to handle what I was wearing. We got into the cab and asked to head back to the hotel. As we drove Cleo put her hand on my thigh and started to slide it up my skirt. This immediately got me turned on and my cock, which had behaved most of the night started to get hard. I spread my legs a bit wider to enable Cleo to fondle my cock through the G-string panties I was wearing. This felt so good that my cock became rock hard and she released it from its panty cage and started to gently stroke it. "I was so proud of you tonight, you were a perfect tranny. None of those guys had a clue what was hiding away in your panties. They were all so horny for you I bet they would have fucked you even if they did find out!" While she was doing this she slid the panties down my legs and picked them up and put them in her purse. I was just enjoying the gentle hand job I was getting. "I think they thought we were both sexy and we both could have had some fun" At that moment we arrived at the hotel and Cleo had the cash ready and gave it to the driver and said to me "Hurry up baby lets get to the room, I want to fuck you" We got out of the cab and I realised that with no panties on and a short tight tube dress on my hard cock could be seen through the fabric as clear as day. I tried to hide it as we walked to our room but don't know how well I did. Fortunately not too many people were there at that time, mainly staff and given that I was in a drunk state I didn't fret too much. We got to the room and laughed at the situation and Cleo made a fresh round of drinks and turned the lights down very low. Then as she walked over to me she said "Tonight your going to get the fuck of your life you sexy slut" "Mmmm I can't wait, I'm so horny" When she arrived she put the drinks down and started to rub my body and lifted the dress to reveal my cock that had again become rock hard. She gently stroked and said "How did you like being a super sexy tranny slut tonight" "It was neat, I felt very special to have all those guys checking me out" "I know, I love the way they always check out my big tits and sexy legs" She pulled the tube dress up and took it off me and said "Lie on the bed baby" I lay back down on the bed and she took off her dress and knelt on between my legs and started to lick my thighs and my cock. It felt sooo good I was totally turned on. After about 5 minutes or so I felt her finger starting to probe around my ass. She looked up at me with my cock in her other hand and said "Spread your legs baby, let me finger fuck you" I remembered we had talked about it during the day so I spread my legs apart for her. "Good girl, you're going to love this" I felt her finger start to probe inside my ass. It was a strange sensation but as her finger got further in I became more and more excited by it. She pulled it out and slid it in a few more times before she slid 2 fingers in. All the while she was sucking my cock and licking my balls. She continued to probe me and then she pulled her fingers out and asked how I enjoyed it. "It just felt better and better as you did it more - it was amazing." She unclipped her bra and let her big tits hang free, then she rolled on her back and said "I bet you want me to do it more don't you?" I nodded yes "Do you like me" I nodded yes again "How much" "I'm so hot for you, I want you so bad. You're the sexiest woman I've ever met" "Well then lick my tits and body baby. Tit for tat" I rolled over and took her big nipple in my mouth and swirled my tongue around it and rubbed her other breast and lovely flat stomach. As I did I could feel that she was taking her panties off and I moved my hand to her crotch. She had her legs together and she grabbed my hand and held and said "Lick me baby" I moved down and licked her stomach and the top of her pubic area. She smelt and tasted fresh and sexy. I was licking around her pubic hair and the top of her thighs when she said "Ohhh baby I cant wait any longer" and spread her legs apart. As she did this I felt something hit my chin and after a moments shock looked down to see a huge hard 9 inch cock sticking up. I looked at her in surprise. "Suck me baby. Just because I have that doesn't make me any less sexy and hot." I looked from her to her cock and back to her again. "Lick me baby, I know you want to, I know you want to taste my big sexy snake in your mouth." She was right. She was still very sexy, and I was horny, (and dressed like a tranny myself) and her cock looked wonderful and big and hard with a bulging head. I thought of the dreams I had been having with all those cocks and sex and how it had made me feel. With my hand I reached up and held another cock for the first time. It felt amazing, soft on the outside and hard strong muscle underneath. I gently stroked it a few times when she said "Lick me baby, Lick my sexy snake" I moved my face towards it stuck out me tongue and licked it from just where her balls were at the bottom all the way to the big juicy head. She shuddered and moaned "Ohhh yesss baby, just like that, lick me more" I stuck my tongue out and did the same again, one big long lick from the bottom to the head and then I swirled my tongue around the head and opened my mouth and slid my lips over the head and down the shaft. Cleo said "That's it baby, suck my big snake" I did as she asked and started to suck and she thrusted her hips up so her cock went a little deeper. I took it out of my mouth and then licked around the shaft and swallowed it again. Now I was really starting to get into it and so was Cleo. Before long we were both in full swing with her thrusting her hips and me sucking and licking her cock. While I was sucking her cock she was telling me what a good job I was doing, guiding me on how to make it better, how sexy she thought I was and how horny I was making her. She also told me what a good slut I was and that this was just the beginning of an amazing opportunity. After a good 10-15 minutes of this she said "Roll over on your back baby, I want to return the sensations" I did as she asked and within she immediately started to suck my cock and finger my ass again. I'm not sure but I think she may have had 3 fingers in my ass this time. It felt great to have her sucking my cock and the anal finger fucking was giving me the most amazing sensations. After a few minutes of this she reached over to the bedside table and grabbed a tube and then went back to sucking me but rather than her saliva as lube she applied some of the real stuff. This helped her to slide her fingers in and out even easier. I was just loving it, and my ass was tingling with the new sensations. Then her fingers were out of my ass and she stopped sucking me and had grabbed an ankle in each hand and pushed them back above me raising my ass in the air. I felt her big cock head just on the entrance to my ass, teasing me. "Tell me how much you want to be my sexy slut baby. Tell me how much you want me inside you. Ask me to fuck you like you have dreamed" I was worked up and I wanted it. If the finger fucking was anything to go by this was going to satisfy some desires I had been having. My ass was hungry for what it was about to get. "Treat me like a slut and fuck my ass Cleo. Give it to me like I want it" "Beg me my little slut, beg me to fuck your pussy" "Fuck me Cleo, please fuck my pussy like a slut. Bury your big sexy snake deep inside me." With that she got her panties from beside her on the bed and shoved them in my mouth. They tasted of her pre cum and her ass. "Bite these, they will help you to relax" and with that I felt her big cock head start to enter me. I bit down on the panties to help ease the burning that I was starting to feel in my pussy. The intensity increased more and more until I let out a whimper. She stopped pushing for a few seconds then started again. The intensity increased and I let out another groan, muffled through Cleos panties in my mouth - but a bit louder this time, she stopped for a few seconds again and then started again. Again the pain and intensity increased and I let her know through a moan and deep breathing. She paused pulled back just a little and then pushed forward again. Then, with a little more of a push, her big cock head had passed my sphincter and was sliding inside me. It felt amazing as the pressure reduced in my pussy. The sensation was hard to describe, like my inner pussy was being tickled as Cleos big cock continued to slide in. My eyes rolled back in my head and I moaned with pleasure. I took her panties out and said "Ohhhhhhhh Cleo that is so amazing, your cock's so big but it feels so good" She replied "I told you you'd love it. Isn't it the best you've ever had?" "Ohhhhh it feels soo good. I never knew how good this was" "So, do you want me to fuck you like a slut?" "Yeah, fuck me like a slut. Give it to me" 'Beg more baby, beg me to fuck you, tell me how you want my cock" "Fuck me Cleo, fuck me like a slut. Pound my pussy and fuck me hard. I want t be your dirty slut" "OK, since you want it so bad I will. Now put the panties back in your mouth and let me fuck you so hard you beg me to stop, but I won't stop. The more you groan the harder I will get, is that what you want?" "Yes baby fuck me like that make me beg you to stop but keep on going" She gave me a very sexy, dirty, dangerous smile and that was when I dawned on me that I was really going to get fucked like a slut - and fucked hard. Given I had never had this before I was not sure what to expect, but figured it would feel as good as the gentle sliding in and out she was doing now. I didn't realise that until my ass was 'trained' to take a pounding from a big cock that it was going to feel like my ass was on getting ripped apart. She pulled her big cock out and said "Bite down baby" and with that she thrust her cock inside me, quickly pulled it out and thrust it in again and again and again and again and continued to do this. I enjoyed the first 4 or 5, I felt unusual and warm but after that it started to feel like my ass was burning. I bit down hard on the panties and started to breath hard through my clenched teeth, trying to absorb the pain. She continued to thrust her big cock in and out of me, each time her hips hitting my ass cheeks a slap sound was made. Then she got a bit quicker - slap, slap, slap, slap. The pain was too intense so I started to scream through my teeth. "Arrrghhh, arrrghhh, arrrghhh, ohhhh, ohhhh" "Ohhh you're enjoying that aren't you, let me fuck you harder" She put my ankles on her shoulder and bent forward so I was bent in half and her face was above mine with her big tits resting on my false ones. I was about to take her panties out of mouth to say stop but she bet me to it and grabbed my hands up behind my head. Then she went for it, really pounding me hard with full 9 inch lunges, ripping my ass apart and getting faster and faster and harder and harder. I started screaming stop through the panties but the sound was muffled and she continued to pound me saying. "Yeah baby, don't you love that! Listen to your moaning" She continued to pound me as I screamed into the panties for at least another 5 minutes or so and then pulled her cock out and straddled up to my face, taking the panties out and putting her cock head at the entrance of my mouth and said "Open your mouth baby and suck me dry" I opened my mouth and she put her head in and started to pump her cock hard as wrapped my lips around her big cock head and I sucked as hard as I could. After a minute or so she was gently fucking my mouth and I felt the first shot of cum shoot out of her cock and hit the back of my throat. Then the next one followed and then again and again. Spurt after spurt of her hot cum was shooting out of her cock and into my mouth as I sucked and swallowed it up. She was groaning and moaning "Ohhhh yeah baby, suck me dry, ohhh yeah, mmmm, suck me, swallow me, ohhhh yeahhh" It was the first time I had tasted cum other than my own and it tasted amazing. Everything was amazing. Sucking her cock, the taste of her cum, the ass pounding I had received. The drink was working and even though my ass was sore, I loved it and I wanted more. When she finished shooting her load she pulled her cock out of my mouth and said "Ohhhh baby that was good. You handled your fucking just like a good slut and didn't make any mess with my cum. How did you like it?" "It felt amazing, I want more" "More what, sucking, fucking or cum?" "I want more of all of it, I want to suck you again before you fuck me like a slut and I want to taste and swallow your hot sweet cum" She smiled as she knew the drinks she had given me were working. "Well, I'm going to do all of the above and I'm sure we can get help form others too." Now, let's have a drink before I teach you some more great techniques. She got off the bed and went and made a drink - one of her herb teas. We drank that and she told me about the first time she had anal sex. It was a great story and a bit similar to mine introduction through her. She was sitting their completely naked and I could see her big cock, soft at this stage but the same size as mine was when it was hard. Then she said "I want to teach you more" and she started to stroke my thigh and around my crotch. I spread my legs apart and said "I want to learn all you can teach me - show me how to make you cum the best you ever have" With that she sat back and said "Then suck my cock again baby and make it hard" I did as I was told and got on my knees and started to lick and suck her just as I had done before. Her cock goy harder and harder as I licked and sucked it and it was amazing how it changed from a soft friendly object into a rock hard object of ass pounding destruction. After about 10 minutes of me sucking her she said "OK baby, time for your first Doggy fuck" She pulled out of my mouth and went behind me and rested her cock on my back. "See how big my snake is baby, that's going all the way inside your tight pussy" Then she put some lube on my pussy and her cock and then placed the head against the opening. "Say please!" "Please Cleo" And with that she started to force her cock inside me again. This time it was easier as I was already a bit loosened from the pounding I had received 20 minutes earlier. She nudged it in - deeper and deeper and I could feel it all the way until after a few minutes her hips were against my ass cheeks. I groaned in pleasure "Ohhhhhh Cleo that feels so amazing. Sooo deeep. Your big cock buried all the way inside me" She leaned forward and I could feel her big juicy tits on my back. Then she said in a low husky voice "Well, since you enjoy it so much how would you like me to make you to be the best tranny fuck around". "Yeah please make me the best tranny fuck" "Good, because you are already on your way to this" Of course by this I thought she meant teaching me how to be fucked by tranny's, not to become one! She continued to slide her big snake in and out slowly but I could tell she was getting more excited. Then she pulled nearly all the way out with just the tip inside me. Then she climbed up on the bed so she was standing above my hips and able to lunge with full force in my pussy. Then she said "Hold on tight baby, time for you to learn how to handle the pounding of your life" The initial thrust of her big cock lunging in me was wonderful. The sensation was amazing, I could feel it going all the way deep inside me. Then she pulled out and did it again, and again, and again. That's when the sensations changed and the warning to hold on became relevant. She got faster and faster and harder and harder. I grabbed hold of the pillow in front of me as she continued to pound me. After only a few minutes the intensity increased. My ass was on fire, and it hurt a lot but for some reason I was loving it - I wanted it more. "Ohhhh yeah Cleo, fuck me like a slut. Pound my pussy. Ohhhhh, Mmmmmm, yeahhh" She continued to fuck me like crazy and I could no longer contain myself. I could not talk anymore and I bit down on the pillow and started to scream into it. The pillow muffled my screams as I let out a howl with each hard pump on my pussy. Cleo was going for it, and it was a full 5 minutes of firm pounding before she started to groan herself which meant that she was getting ready to shoot her load. "Do you want me to cum in your pussy baby, do you want me to fill you with my cum" My face was still buried in the pillow but I managed to get out a grunt of yes. "I didn't understand that. How much do you want me to cum inside your pussy" I released the pillow from my teeth and managed to reply in between my groans. "Arghhhh, arggghhh, yessss, ohhhhhh, cum inside me, arghhhh, fill me, ohhhhhh" With just a couple more pumps I felt her cock spasm and start shooting cum deep inside me. She slowly withdrew as she emptied her load so that the last of the spurts was just as her head exited my ass. I fell flat on the bed and tried to relax a bit. She climbed off and complemented me on my performance as a slut, and that I was a pretty good fuck for a beginner. She told me I should rest for a bit, and that when I got up to be careful of all her cum that will start to run out of my pussy. She then went to the bathroom to clean up while I lay there and continued to recover from the pounding I had received. She came out of the bathroom fully naked. I looked up and admired her sexiness. I got up off the bed and squeezed my ass as tight as I could to try to prevent cum from spilling out. Sure enough, because of the stretching I had received, I was unable to seal the gap and I started to feel it running down the inside of my legs. I quickly made it to the bathroom and turned on the shower, took of the lingerie that I was still wearing and had my shower. I returned to the room and Cleo gave me a sexy little lace nighty and matching G-string panties to wear for the night. She had also made our bedtime cup of herbal tea and we got into the bed and relaxed. We sort of chatted for a bit before I was fast asleep. Again that night I had dreams of groups of guys fucking and cumming all over me, me swallowing their cum and other crazy scenes. I woke up in the morning wondering if the previous night was for real when I felt something hard pressing into my back. I reached around and sure enough realised that Cleos cock was hard and ready to play. She was still snoozing so I stroked it a couple of times. This immediately aroused me and I decided to give her a pleasant surprise. I turned over and slid down and started to lick and suck her. She rolled on her back and started to gently groan. I continued to do this for about ten minutes when she said "So good baby, suck me hard" I knew what this meant, more of her cum so I started to suck her head as hard as I could. She placed her hands o the back of my head and started to force me down on her cock. Each time I was able to take her cock a little bit deeper until she was all the way inside my mouth. At that moment I felt the surge that I have the previous night and could feel her cum shooting into my throat. She pulled out and the last shots filled my mouth and I swallowed that also. We got out of bed and I had a morning shower while she made a cup of tea and the drinks. When I got out of the shower as I was drying myself I noticed a difference. My nipples were a lot bigger with the areola was twice the size of what it was before and there was small breasts there. I felt the nipples and they were certainly more sensitive than before. This made the nipples go hard and they certainly were bigger than before. I admired them in the mirror and guessed that if I wore a bra it would probably be an A size cup or trainer bra. This made my cock go hard and I put my hand down to stroke myself and noticed that my cock was also bigger than the previous night. It had probably grown about an inch and was 7 inches. This altogether made me very horny, and I wanted Cleo to fuck me again. I walked out of the bathroom naked, with hard nipples and a hard cock. Cleo had just finished making the drinks and turned around. "Mmmmm, don't you look so sexy" I noticed her cock started to harden when she saw me and so I walked up to her, reached out and started to stroke it. She returned the favour and said "I think we need to get on the road baby, perhaps we could do this at a rest stop on the way! Now let me get you dressed." We went over to the bed and there was a bunch of clothes there - sexy female clothes. I couldn't see my bag anywhere. "Where are my clothes"? "You won't need those ugly man clothes anymore baby. You can wear mine so you feel sexy all the time" "But what about ..." She interrupted me. "No buts, if you want to have fun with me, and I can see you do" she looked at my hard cock "then this is how it will be. Your man clothes are in the car, but I don't think you will need them anymore." She reached over and grabbed the suspender and started to put it on me. I enjoyed the feeling as she wrapped it around my waist. Then she grabbed some stockings and I slid them up my legs. They felt wonderful and I knew I would not wear man clothes again. There was no bra, just a white lace G-string, a tight hot pink T shirt top and a short denim mini skirt. She gave me a blonde wig that was long and in a pony tail. The final item was a pair of my running shoes that she had taken from my bag. I looked at myself in the mirror and with my perky little breasts thought "What a sporty looking chick"! She got dressed in her denim hot pants and a tight T shirt that had to stretch to get over her big breasts. She also put on running shoes and we headed to the car for to continue our journey. The conversation was different today. It was only about life as a tranny. The different ways of having sex, dressing like a female, acting like a female. She was really training me for the future. We had been driving for a couple of hours when I was so horny after listening to her that I had a craving for sex. My ass (which she now called my pussy) was tingling and my cock was dying to get out of its panty cage. I said "I'm so horny. Can we stop and have sex. I want your cock in my pussy and then I want to suck all your cum out of it". She smiled and said "How about I drive and you can suck my cock. Let's pull over and change". We quickly did this and started to drive. I waited a little until she was confident with the car and then with my hand reached over and started to play with her cock through her panties. As I felt it firm up I released it and continued to stroke it. When it was hard I bent over, opened my mouth and wrapped my lips around her glorious cock head, swirling my tongue around it. The pre-cum tasted delicious and I tightened my lips and moved them down the shaft. She groaned softly "Mmmmm ohhh baby" I tightened my lips and raised myself and when I got to her head I swirled my tongue around again. Then I lowered down again and continued to do this getting more and more vigorous and with my hand gently caressed her balls. She groaned and moaned and I could tell she was loving it. It was only about 10 minutes before she was humping my face and then she pulled over at the side of the road and grabbed the back of my head and forced it down over her cock and started thrusting harder and harder until she said "Suck baby, suck me hard, but don't swallow. I want to see all my cum in your mouth" I started to suck on her and I again felt the sweet taste of her hot cum shooting out of her cock and filling my mouth. I didn't swallow and once her balls were emptied. I opened my mouth and showed her all the cum. "Good slut, you can swallow now" I closed my mouth and swallowed, and then licked my lips to get any spare drops. We continued on our way until we got to our destination for the evening. As we drove we continued to talk about my tranny training, including my voice pitch, the way I walked, my hand and body movements etc. We eventually got to our destination and found a hotel. We only needed a double bed now and we quickly found one. I was super horny after sucking her off but not getting any myself, so as soon as we got into the room I said to Cleo "How would you like to fuck your sexy slut"? "That depends, do you want me to teach you some new tricks and a new game"? "Ohhh yes please Cleo, teach me some new slut tricks and a new game" "Mmmm. Then I cant think of anything else I would rather do right now. Tonight we are going to have some serious fun baby. We are going to play the 'yes' game. Now, take of your clothes and lie on the bed on your back" I did as I was told. Cleo opened her bag and pulled out some rubber straps and tied each of my wrists to each corner of the bed head. "Have you ever been in a situation where you had to accept what ever was happening to you, no matter what"? "No"? "Well, then this will another new experience for you. I'm glad it is me giving you your first, but it won't be the last. Now with the yes game, it's pretty simple, I ask questions and you have to say yes. Do you think you can manage that"? She went over to her bag again and pulled out another back and brought it over to the bed. She opened it and turned it over and tipped out the contents. 5 very big dildos landed on the bed along with some other devices. As she did this she looked at me and said "I'm going to stretch your pussy so much tonight baby - you are going to love it. Your ass is going to look like a whores pussy when I have finished. Doesn't that sound like fun" "No" I said with fear in my voice She reached up and grabbed my balls and gave them a squeeze. I wriggled to try to get away and she said "No is not what a good slut says to her mistress and against the rules of the game. I will let you away with it this time, but in the future that sort of behaviour will be punished. You can see here the sort of punishment I can inflict for saying no - unless of course you want it". She squeezed a bit harder and swatted my cock. I tried to move my arms but I couldn't. My legs thrashed a bit as I tried to escape the pain. She grabbed my left leg and said "I see I will have to control these". She pulled my leg over my head and with the long end of the tie from my hands tied my ankle to the bed head. Then she did this with the other leg. I was now pretty much immobile with my arms and legs both tied to the end of the bed. "Ohhh your pussy looks so open and inviting slut, it is just begging for me to fuck it. Do you want me to fuck you"? I knew what happened last time, so it was a simple answer. Also, all the drinks I had been having over the last few days were kicking in and I was getting pretty excited. "Yes" "Yes what"? "Yes please Cleo" "And do you want me to fuck you hard and deep" "Yes please Cleo" "So hard that your pussy feels like it is on fire" "Yes please Cleo" "Good baby, you learn fast" With that she got on the bed, kneeling so she could place her now deliciously hard cock at the entrance to my ass. "Do you want me to just thrust it in with one deep long lunge" "Yes please Cleo" "Are you sure about that baby"? I made the mistake of thinking she was giving me a chance. "No" "Ohh you cheeky little slut. You'll wish you said yes" With that she thrust her big 9 inch cock all the way inside me with one hard lunge. I let out a scream - the pain was so intense. She pulled out and picked up her panties and shoved them in my mouth and then thrust her cock in again. I screamed but this time it was muffled by the panties. She pulled out and then drove it in again and again quickly getting to the 'hard fuck' level of pounding my ass. I just lay back and tried not to scream and to relax my ass so the pain would not be as much. She continued to pound me, giving long thrusts of her cock and hips deep into my ass and after a good 5 minutes I was ready to stop. "Do you want it harder slut, do you want me to fucking pound your pussy" There was only one response - I couldn't talk so I nodded "Yes" With that she got off her knees and stood over my open ass. She paced her big juicy cock head against my pussy, looked at me and smiled and said "We're just warming up baby, keep on saying yes and you'll enjoy it. Now bite down on those panties" With that her cock thrust deep inside me again and then she quickly pulled out and then again and again and then once she had momentum got the bed bouncing to help the impact of her thrusts and my rebound. There were big slaps as her hips hit my ass checks. I was starting to enjoy it now due to the special tea I had drunk over the last few days and as my ass was getting looser. I just focussed on my breathing as she got the rhythm going, holding on to the bed head. After another 10 minutes or so she got harder and harder and I new she was getting close to cuming. Then she pulled out and said "Ohhh baby, I want to cum so bad. I'm so horny for you but first I need to fuck you with my toys" With that she went over and put on a belt like device and grabbed one, which was about 10 inches and fatter then her own. She clipped it onto the belt, rubbed some lube along the length of it and stepped above me. Then she placed it at the entrance to my ass and said "Do you want me to stretch you more". I only had one option and nodded yes "Ok then" And she started to force the dildo in me. I could definitely tell that it was fatter than her cock as my ass entrance started to get stretched and the pain increased. Once she got the head she said "Bite down on those panties baby" When she saw I had done that she forced the dildo the rest of the way in to the hilt in one move. I screamed but the sounds were muffled by her panties. She pulled out and forced it in again and again until after about 10 minutes my ass was comfortable with it. She could tell as I went from screaming into the panties in pain to groaning in pleasure. My ass was loving the pounding and stretching it was getting. "I think your handling this a bit easy now, time for more" Then she pulled the big dildo out and un-clipped it and threw it on the bed, bent over and picked up a bigger one. It was only a little longer, but definitely fatter than the last and it had quite a big head "Check it out baby, 11 inches of hard, fat cock just dying to rip your pussy apart. Do you want this deep inside you"? She waved it in front of me before clipping it on. Again I only had one choice and nodded 'yes'. "Ohhh you are such a horny slut - I knew you would like it." Then she got her lube and rubbed it along the full length. "Don't you wish your cock was as big as this baby"? Again I nodded 'yes' With that she placed the head at the entrance of my ass and started to force it in. The head was much bigger and the pain intensified as it stretched me and I started to scream again. "Yeahh baby, take that big fat cock" I waved my arms around and tried to break free of the ties but couldn't. I tried to kick my legs but she had those well under control and said "Do you want me to squeeze your balls again? If you don't keep still and take it like a slut" I didn't answer as I didn't want to say no or yes. She continued to force the big dildo in and I continued to scream into the panties. I could feel the big head inside me - forcing it self deeper and deeper. Eventually, after about 5 minutes, I felt her hips against my ass. "Ohhh baby, you took it all the way. I'm so proud of you. Now, would you like me to start fucking you with"? I could only nod 'yes' With a very cheeky smile she said "I had a feeling you would say that"! She pulled it out and then slid it in again, out and in and out and in until again my ass started to relax and enjoy the sensation as the big head buried itself deep inside. After a while my ass started to relax and I was again enjoying it until after about 15 minutes she pulled out again and quickly unclipped the whole belt. Her cock was rock hard again and she shoved it in and just started to fuck me as hard as she could. It felt wonderful to have Cleos cock pumping in and out after the big stretch my ass had received. Then she buried her cock as deep as it would go inside me and held it there, gyrating her hips around and around. Then I felt her body tense as the first shot of cum shot deep inside me. She continued to gyrate until her cock was empty of cum. Then she slowly pulled out and reached forward and grabbed the panties that were in my mouth and said "Baby that was sooo good, did you like the yes game?" I nodded 'yes'. "Do you want to play it again tomorrow"? Again I nodded 'yes' "Good I thought you would" and with that she pulled the panties out of my mouth. Then she untied my wrists and I got up and went to the bathroom. When I got back she had a cup of tea and had laid out the same bedtime wear as the night before. She told me to put it and of course keep my false breasts in place We had room service for dinner and that chatted until I fell to sleep. I woke up to feel her big hard cock pressed against my back as she spooned me. It felt so good - and immediately I noticed that I was also rock hard. I reached around and started to play with it. She whispered in my ear 'Mmmmmmm, what a nice way to wake up. Suck me baby" I turned around and slid down the bed and started to lick her cock and take the head in my