Lisa's Awakenings, Chapter Eight
Finding my Tranny Jamie

After that last time with Aaron, as he was fucking me as we were watching the tranny get fucked in the porn video and deciding I wanted to have somebody watch Aaron fuck me as Lisa I was trying to figure out how to find somebody that would do that. Over the next couple of nights after work, I would scroll through different adult sex dating sites and was reading profiles and decided that I probably wasn't ready yet to have another guy watch us and I wasn't sure about a woman also, but seeing how some of the crossdressers/trannies were, I narrowed my search to them. On the third night I clicked on this profile and my breath caught for a minute because at first I just thought she was a beautiful woman. After reading through everything she had written on her profile I knew she was the one and when I clicked on her pictures, they were about three dozen of them with her indifferent poses in different lingerie and a couple of them she was braless and had what I considered perfect tits! The pictures where you could see her panties, you had no clue that she was a tranny except for two of them where the panties were very sheer and you could see a dick tucked down. The last few pictures you could see that she was hard in her panties and the next to last one you could see the head poking out and the very last one had her dick half hard hanging out of the side of her panties and I was so hard then. I saw there were a couple of other folders of pictures but were labeled Members Only along with a section of videos again marked Members Only. I quickly got my credit card joined, making a quick short profile and then went back to look at the rest of her pictures. She obviously had somebody she was comfortable with taking her pictures that knew how to capture her in her beauty. The first one she was posing seductively in a lacy bra panty set and the pictures continued as she removed her bra and then was cupping her beautiful tits and then showed her thumbs in the waistband of her panties and you could see her panties being pushed down until they were mid thigh but her dick was still tucked back between her legs with her legs closed being demure at the same time. This was obviously designed to make the reader such as myself want to see more and then the next three in a row showed her dick hanging down, then one with it half hard and the third one was fully hard and if she had walked into my room unannounced that second I would have eagerly taken it in my mouth without a word being spoken! The next folder or pictures of her using various toys and cumming. The next folder of pictures were of her sucking dicks. There were a couple of her sharing/sucking a dick with another tranny and then a couple of pictures of her and the other tranny sucking each other. The last folder had various pictures of her being fucked and cumming from a guy and some of her fucking a woman and some of her fucking a guy and then finally some of a guy fucking her as she was fucking a woman. God I was so horny and hard and leaking, but something just made me not masturbate yet. But I did run in to my bedroom and inserted a small butt plug into myself and then pulled on some panties and a little teddy type top. I'm not even sure why I bothered with the panties because when I sat back in the chair and was squirming feeling the butt plug inside me I was so hard I could barely keep myself in the panties. When I finally opened up the video folder there were maybe two dozen videos there and when I clicked on the first one it was titled, Edited down because he fucked me too long to record it all. Since it was the first one in the folder it must have been one of the first ones she had done because you really couldn't see her, just her beautiful ass as she was on her hands and knees and a finger applying lube and then fingering her before you see a lubed cock slowly push into her and you could hear her moans and squeals as she was being fucked for a couple minutes and then it jumped to him saying, Oh my God baby I can't hold it any longer I'm going to cum in you sweet pussy and you could hear her moan, Yes, Yes, Do it, give it to me! You could see him push in and hold still for a minute and then he pulled out and shot a few spurts onto her back before pushing back into her and hearing her moan, Oh my God I fucking love it! and then the video ended. I was stroking myself but taking my time because I knew I was close. I clicked on the next video and this had a title also that said, He had been fucking me so good bringing me to the edge when I remembered the camera. This one started seeing her getting on a bed on her back pulling her legs back and open as the guy panned up on her saying, My God you really are beautiful. She smiled and said, You've been fucking me so good and you brought me to the edge a couple of times, now put that dick back in me and fuck me and make me cum for you. You could see the man's cock push inside her and she gasped and moaned, Oh my God your cock feels so good just fuck me baby make me cum! You could see him fucking her good and see her beautiful tits wobble back and forth with each thrust into her and she started panting and then moaning louder, Oh my God Oh My God keep doing that, make me cum baby I'm so close! Then the camera looked down and zoomed in so all you could see was the cock thrusting inside her and her just holding the base of her dick up and it was already leaking pre-cum and her moans changed to squeals and then she cried out, yes Yes YESSS and just stroked the base of her dick a couple of times and she just started cumming and the camera panned back some and you could see her shooting her cum on her tits and her stomach. The guy groaned out, Oh fuck baby you are so good I'm going to cum on you now and he pulled his dick out and stroked it a couple of times and started cumming on her dick and stomach and tits and I couldn't control myself and I came also.
After getting myself back under control I made a few quick additions to my little profile and then sent a message to her. Her name was just listed as Jamie123. I started off by telling her I thought she was a very beautiful woman and her pictures had definitely turned me on and then I told her my age and explained how for a couple of years I have worn women's lingerie and had online cyber sex as a girl and then briefly that things that happened between my best friend and I and that now I was dressing as a woman and having sex with him as his girlfriend and that we wanted to have somebody watch us because we thought it would be erotic. I reread everything and taking a deep breath I hit send. Surprisingly enough, about 5 minutes later as I was ready to sign off, I got a reply from her. We instant messaged back and forth for a few minutes and then she asked if we could speak on the phone tomorrow nigh,t which I agreed to. The next night when she called she explained from the very beginning that this was not going to be a sex call, that we should look at it as more clinical and discuss things professionally and I told her absolutely. She continued that she doesn't normally respond to her inbox messages right away but after reading mine it just seemed different than the normal guys that just wanted to fuck and then after we had been chatting she realized there was stuff going on with me and there were things that I had not said and she wanted to talk about them. She gave me a brief rundown of how she didn't consider herself a male, that even from a very early age she just felt like a female trapped inside a male's body and that overtime she had learned to accept it and that she was taking hormones which is what gave her the tits she has and that she was waiting for the right time down the road to do a full transformation from male to female and that for the time being she was just trying to understand and embrace who she was and enjoy sex like an adult and enjoy the best of both worlds. We talked some more and she asked me questions and I responded honestly and we realized we had been talking for an hour and she wanted to know if we could meet up on Saturday night to actually meet and get to know each other better. I’m not saying we are going to have sex but you seem like a really decent person that I would like to get to know better. I agreed that something about talking with her made me very comfortable and admitting to myself these feelings I was having an experiencing and thought that maybe if we met in person we could talk more and who knows whatever. She said, I tell you what, how about when we meet, you be Lisa and we can talk and get Lisa's feelings also. I was okay with that and we set a time for her to meet me Saturday night.
Saturday afternoon rolled around and I was a huge bunch of nerves…could I really go through with this meeting somebody as Lisa? Did I even know who Lisa was? But then remembering how beautiful this woman was and after having a couple of drinks I decided to go through with it.
I finally decided on this bra and panty set because I like the way the seam of the panties felt against me when I pulled the back up tight between my butt cheeks, even just walking around it would rub just against the edge of my hole. I only had the two short skirts and a two blouses I had bought to wear when with Aaron so I chose one of each of them and then tried to put on some makeup and a wig I had bought and after deciding that was the best I could do and after another drink to try to calm myself I heard a car pull into my driveway. When I saw her through the window, get out of her car and walk towards the door I was amazed again at her beauty. When I answered the door she just smiled and said, Hi Lisa. After holding the door for her to walk in she said, Thank you so much for having me over so we can get to know each other better. Somehow half of my nerves just disappeared and she was even more beautiful close up and in person. I led her to the living room and then said, Oh I'm not being a proper host, would you like something to drink? Looking down at my almost empty glass on the coffee table said I'll just have what you're having. I pointed to the sofa and said, Make yourself comfortable I'll be right back, but instead she followed me into the kitchen. I poured two fingers of bourbon into each of our glasses and handed her one and she just threw it back swallowing and said hit me again and I promise to savor this one. I did the same and then we carried our fresh glasses back and sat on opposite sides of the sofa and we started chatting and the more we talked the more comfortable I became with her. Pretty soon we were actually discussing sexually explicit things and I really wasn't getting too excited by it because of the way she made me feel comfortable and that we were discussing things and not trying to be sexual. After sometime when our drinks were gone I asked if she wanted another and she said, Sure why not if you are. She got up with me and followed me back into the kitchen as I poured us another fresh round and then she said, Lisa may I help make a few suggestions to you for your makeup and hair? I said I would gladly take any advice. She asked where my makeup was and if we could go to where there was a mirror so we went to my bathroom. She said, do not take this as criticism because I know you're new at this and some of what you've done is fine but with your complexion and eyes and hair color we need to make some changes. I didn't even realize she had her purse with her until she pulled out a makeup kit and some makeup wipes and kind of wiped my face clean and then explained the coloring as she applied new makeup to me and when she was finished and had me look at myself in the mirror I was amazed at the difference! Then she surprised me as she said, Okay let's see what's under these clothes, as she reached up and started unbuttoning the blouse I was wearing. Once it was unbuttoned, she opened it up and then traced her fingers around the edges of the bra and said, Very nice and then proceeded to remove her blouse also. Then she said, A good proper bra should fit comfortably and enhance what you have creating desire in your partner. And then she unzipped her skirt and let it fall to the floor standing in front of me so I naturally look down and admired the sexy lace edges of her panties and again could see no sign that she had a dick. And then without hesitation reached and unbuttoned my skirt letting it drop to the floor and said, Okay you made a good choice with the panties and bra being a matching set. But panties should fit right and she went on to explain about body shapes and types of panties. I was comfortable enough with what was transpiring and curious also so I said, May I ask a question? She said sure. I said Well obviously I’ve seen your pictures and a couple of your videos and I know you have a dick, if that's what you call it. And she quickly interrupted me and said, Lisa I consider myself a woman 100%, just stuck in this body so I just call it my clit. I said, Okay, how do you keep your clit hidden like you do? Standing here in front of me this close I can't tell you have a clit, but look at me you can see I've got a dick. She gave a little laugh and said that's only natural to wonder about that and I don't mind you asking and I'll tell you and show you. She continued before you pull your panties all the way up you basically have to reach from the back and grab yourself and pull you down and back under yourself between your thighs and then pull the panties up tight to keep you tucked down and back like that. And then looking me dead in the eyes put her thumbs in the waistbound and push her panties down to mid thigh and then opening her legs a little her clit finally fell down into view and even though she was not physically aroused at this point I couldn't help but lick my lips and imagine it in my mouth. I looked back up at her and she was grinning and said, You know I like you more and more because I can see those thoughts running through your head right now, but try to control yourself just a little bit longer and don't think about sex, just concentrate as this being clinical. She said now lower your panties like I did, which I did and tried not to think sexual thoughts as I was standing in front of her with my dick hanging out. She said now try to squat just slightly and use your hand and reaching from the back and under grab yourself and pull you down and back up to the back and then squeeze your legs together as you pull the panties back up. Once I had done that she took my hand and placed it against the front of my panties and said, See that’s so much better. Then she grinned and said, And being like that when you start to get excited you can just squeeze your thighs together on yourself to keep it down and hidden. I couldn't help but look down and saw that her clitty had gotten almost an inch longer and thicker but was still hanging down. I heard her say I can see you looking at me and I can see you have a question so go ahead and ask. I hesitated and then said so you've told me that you live your life as a woman, and pointing down between her legs I said, But you have to deal with this all the time, so how do you do it? She just laughed and said, Yes since I am a woman, this thing here between my legs has become more of a minor inconvenience for my everyday life and if I just keep it tucked away I forget about it. And I know I must have started blushing because she gave a little giggle and said, I can see something on your face, come on out with it, we're just being open about things now. I took a breath and said, Okay I think you are a beautiful woman and your pictures on your profile just show that beauty but when I saw the one video of you I was surprised at how big and hard you were. She said I'm one of those, to use the expression, a grow-er not a show-er. I didn't think as I blurted out, Well what you showed then was fantastic and I wanted it and oh my God the way you came! Okay I was stroking to the video and watching you cum made me cum. She blushed a little and said, Yeah something with him, especially as long as we had been enjoying ourselves, he can usually do that to me, but believe me that does not happen all the time. Then placing her palm on my cheek as we looked at each other she said, Lisa I believe we are at the point where you need to make a decision and I am fine with whatever you decide, so should we go back to the living room or should we go to the bedroom? I thought about it for maybe only a second and then said, Will you take me to the bedroom and teach me the pleasures of being a woman? Her answer was to step up and pulling her to me we kissed and the kissing quickly ignited the fire that had been smoldering inside me for her. When she pulled away a minute or two later her face was already flushed and she said, Wow you are a great kisser! Then taking my hand said, I think you and I are going to enjoy some fantastic sex!
We were soon wrapped together on the bed, passionate kissing and hands exploring each other's bodies and when she finally took her bra off I couldn't help but let out a little moan of desire as I reached for her perfect tits and as I was cupping them and my fingers playing over her nipples her eyes were closed and she was letting out soft moans. With no words spoken our mouths and tongue started exploring each other and before long we were 69ing and I loved the feeling of her hard clit in my mouth as I sucked and slurped and running my tongue all over it up and down and moaning most of the time and finally she gasped and said, Oh my God Lisa your mouth feels amazing. I've got to ask how many cocks have you sucked? I panted, only three, two guys in college and then finally Aaron. She said, Damn what you were doing to me if I didn't know you were telling me the truth I would have bet you had sucked quite a few cocks to learn to be able to do what you were doing to me, it just felt so damn good and natural and effortless on your part. I said, Well those times in college was just drunkenness and I never thought about it until Aaron was in my mouth and I admit I really enjoyed having his hard dick in my mouth, that it was just doing something to me that I wanted to give him that pleasure and now with you, with your beautiful clitty, it's just making me feel things I've never felt before and I just want it. She turned to crawl back up to me and as we were passionately kissing her hand was between my legs behind my balls her fingertips lightly touching me sending sensations through me as my legs kept opening and my hips arched against her hand a few times and she pulled back slightly and looking down at with me with what I can only describe as lust on her face she said, Do you really want my clit? How do you want it? Just be open and let me hear you say it. As her finger finally rubbed around the edge of my bud and was tapping it lightly I groaned out Jamie I want to feel your clitty inside me, I want to feel you fuck me with your clit and make me feel like a woman! As she started to move down between my spread open legs she said, Well we all know that most women love their pussy being licked before they get fucked and I bet you do too don't you? I said, since I’ve only been with Aaron, he has, but just briefly, usually it's lube and his finger that gets me worked up. Jamie said, I'm glad you said that, where is your lube? I pointed to the nightstand drawer and she got it and then crawled back down between my legs and then whispered, Just relax Lisa and enjoy it because I love licking virgin pussy, well almost virgin, but I understand how you feel about sucking cock and wanting to pleasure it because I'm the same way whether it's sucking a hard cock or eating pussy. True to her word I was very quickly moaning and gasping and arching my hips up to her face as whatever she was doing to me was sending shivers and tingles through me and as I was moaning and squeezing my chest through the bra I really was beginning to think of myself as a woman because of what she was doing to me. I was getting to that point where I felt I needed something inside me and she must have just known from experience because I felt her tongue replaced by her finger and knew she was getting me ready and I was aching and craving to feel her inside me making me a woman. I felt first one finger slip inside me easily making me moan and she whispered, You are so horny that slid inside you so easily. Then a moment later I felt some more pressure and now she had two fingers wiggling in and out of me sending my hips shaking and finally I gasped out, Please Jamie I want want to feel you inside me, oh my God I need to feel it, please you're driving me crazy, please let me feel you in me. She said, Lift your hips up and when I did, that just forced her fingers into me deeper as I felt her push a pillow under the back of my hips. I guess you could say I was whimpering in desire as she pushed my legs back and open and then felt the head of her clit rubbing up and down and around over my hungry aching hole and I gasped out, Oh my God Jamie don't tease me anymore you're driving me crazy, I so want and need to feel you inside me. I felt the pressure as she started to push but I was so ready and wanting it that she easily slid inside me and even when she stopped to let me get used to it there was no pain and I tried to reach to grab her hips saying, Yes yes please don't stop please I need to feel you please and I was gasping as I could feel her slowly stretching me as she pushed slowly more and more of herself into me and I heard myself moaning, Oh my God yes oh fuck yes oh God Jamie I need it please please give it all to me I want to be full of your clit. I finally felt her deep inside me and groaned as our bodies were pressed together and she bent down and we started kissing as she just slowly moved inside me, sending pleasure throughout my body and I groaned out, Oh my God it feels so good, your clit deep inside me, oh my God I needed this, I wanted and needed to feel your clit doing this to me. She said, Lisa your pussy feels like it's on fire and is so wet and soft on my hard clit inside you. I really don't know what she was doing but I was feeling things like a woman that I hadn't felt quite the same as with Aaron. I moaned out, Oh my God Jamie I can't believe what your clit is doing to me, I've never felt things like this before and I don't want it to end, I just want you to just keep fucking my pussy with your beautiful clit, I love being a woman and fucked like this. I cannot honestly say how long we fucked, but it felt like a long time as she just kept changing speed and depth and intensity and just kept taking my senses to a higher level than I've ever felt before. She kept saying about how good her clit felt inside my pussy and how good my pussy was and how hot it was fucking me and things like that and the dirty talk was just adding to everything. Then when she pulled all the way out of me making me gasp and then rammed herself all the way back in deep and then pulled all the way back out again and did it again I squealed out oh fuck oh fuck yes Jamie yes fuck me with that clit, just keep fucking me, use me, fuck me until you can't last any longer and then you better cum deep inside me because when you do I'm going to lose my mind! Once or twice, I reach down for my leaking bouncing dick and she just slapped my hands away. Even though Aaron had fucked me and had made me cum, what Jamie was doing to me was levels above that and I knew she was going to make me orgasm like I've never felt before because I was feeling sensations inside me slowly starting to build in intensify as I was biting my bottom lip. When she wiggled around slightly, now with her legs on the outside of my hips, each thrust inside me was ratcheting up the sensations I was feeling and I fully knew she was going to make me cum soon and I told her so. She gasped out, Oh my God Lisa, the feeling of your hot pussy quivering on my clit is so intense and I want to just keep fucking and fucking and fucking you it feels so good but I'm not sure if I can handle the intense pleasure much longer! Something about hearing her say that along with the intensity of her thrusting, the way it was hitting and rubbing inside me, the way she was fucking me took me to the very edge and I cried out, oh my God oh my God Jamie I'm almost there you're going to make me cum and I want to feel you cumming in me, please Jamie I need to cum, I want us to cum together, oh my God oh my God oh my God. Stars were starting to spin in my head and sensations inside me we're at the peak of explosion and I just started shaking and spasming and it felt like electricity was coursing through me as Jamie cried out, I can feel you I can feel you I'm going to cum, I'm going to cum in you, I can't stop it oh fuck Lisa yes Yes YESSS and as she thrust in deep and hard inside me, everything just exploded inside of me and I just started cumming and cumming, my throbbing dick just twitching and jerking and shooting more cum on me as fireworks we're going off in my head as every nerve in my body jumped to its peak, the orgasm that was surging through me I didn't even feel Jamie coming in me anymore until she finally collapsed down on top of me, our bodies panting and heaving together until several minutes went by and we could breathe again. She pushed herself up on her elbows looking down at me with a huge smile on her face and said, Wow you really came hard and boy did you shoot, all the way up here as she leaned down and I guess licked some cum off my face and then said, And here and here and here and each time leaned down and licked my chin and my neck and my throat and the top of my chest and then opening her mouth showed me my cum she had licked up and then bent down and kissed me, feeding it back to me which I eagerly took. Then she cupped her tits and started rubbing them on my chest and stomach in my cum and then somehow still keeping herself inside me was able to push up enough to hold her tits near my face and without asking I started licking her tits until they were clean and by that time I could feel her as she slowly slid out of me and I could feel some of her cum dribble out and run down between my cheeks and I just wiggled a little enjoying the pleasure. As Jamie rolled over and curled up next to me she said, So Lisa was it as good for you as it was for me, laughing. I let out a long slow, OH, MY, GOD! I'm not lying when I say that was the most intensive orgasm I've ever experienced in my life I really thought I was going to pass out from the intensity of it my whole body was cumming. She leaned over to kiss me on the cheek and said, Even though I wasn't quite there yet, when you started cumming, your pussy just seemed to clamp on my clit, pulsating on it from your orgasm and I felt like I was never going to stop coming in you. I quickly said and by what I feel leaking out of me you definitely did that! She giggled a little and said Good! and then continued, I haven't had sex with a lot of girls, spelled g u r l, because that's what we are known as, but I do admit that that was probably the most fantastic intense sex I've had with a gurl. I leaned over and kissed her on the cheek and said, Well from what I saw in the one video was that you enjoy and have orgasms from a guy also and maybe this new friend of yours, what's his name, Scott, can give you an orgasm like you gave me. She looked at me with this big wide-eyed look as a little smile crept into her lips and she said who knows, I learned a long time ago the expression Never Say Never.