Lisa's Awakenings, Chapter Twenty
Lisa Gets Her First Facial

Because of the relationship Jamie and I have now, it was getting very easier to slip back and forth between myself as me and my internal woman Lisa. Jamie and I would talk on the phone or text each other almost every night. Thursday night I got a text from Jamie that just said, I've got to call Lisa in 15 minutes! I just replied back okay. 15 minutes later my phone rang and I answered, Hey Girlfriend, and she giggled and said, How is my favorite pussy? Then she went on and said, I've got a proposition for sort of a new experience for you. She didn't say anything immediately, so I said, Okay go ahead lay it on me. She said, Okay remember I told you there was one guy that he just likes to watch me use a toy and get myself off and then as I was cumming he would step up and cum on me also? I said yeah. She continued, Well the first time I did it with him was a couple of years ago and it was hot to me at the time, having somebody watch me get myself off, but it's been the same thing every time and the last time I almost couldn't get myself off, it just wasn’t fun anymore. I had decided I wasn't going to do it with him anymore. Well he's taking a liking to you from the pictures and videos on my page and has made comments more than once that he wants to come on your face. I just kind of went oh wow. She said, Well he's messaged me everyday for the last three days that he really really wants to meet the two of us this Saturday. Basically what he wants is to watch the two of us make out and maybe share a double dildo together. Then he wants to watch me fuck you until you cum on yourself and he said depending on his excitement he may want you to suck him while I'm fucking you. But what he did make clear was he wanted to watch you cum and then wants me to cum on your face and then he will cum on your face also. Then she giggled and said, Think of that as a right of passage, getting a facial they call it. So it would basically just be you and I having fun as he watches, maybe or maybe not have to suck him, just having two people cum on your face. So, what do you think. Well, I should also add that I have had some comments and suggestions from people about what they would like to see. So while we play with the double dildo together I want him to take some pictures and videos of you and I to add to my profile. So what do you think? But if you want to go through with this, then on the way there, and then she giggled, we have to stop at this adult toy store and buy a double dildo together.
I only hesitated a second and then said so let me get this straight, you're asking if I want to meet up with you, make out with you, share a toy with you, have you fuck me and make me cum, all while a guy watches us and jerks off and then I let you both cum on my face, that's it? Well, I guess that's pretty much a no-brainer. What time are we going to meet, laughing. She laughed also and said, Well there is one more tiny little thing I haven't mentioned yet but that's only because I didn't think it would really matter. He wants us to play it out as if you have never played with another woman and I seduce you and then have my way with you and he wants you to wear white or pink and me either red or black. So, I figured this would be the perfect time for you to wear those white stockings and that halter bustier panty set I bought you. I said so I'm supposed to be a virgin to playing with a woman and you ply me with alcohol and seduce me and have your way with me and we all get to have an orgasm. I don't see any problem with that. Tell him to spring for a good bottle of whiskey and I will definitely be your hesitant nervous friend in the beginning. Then Jamie gave a little laugh and said, I think you and I are definitely going to enjoy it more than him. Especially as you and I go to the store and buy a toy we are going to share for him.
Saturday afternoon after going through all of the preparations, I was standing there looking at myself in the mirror and could see an excited virgin, if you want to call it, looking back at me. I went to my closet, which was now getting full with the women's clothing I had been buying, and picked out a skirt and blouse. After checking to make sure that everything looked just right, I was putting some things together in my new purse when I heard Jamie pull into the driveway. Putting on some heels that weren't too high, just to appear like any normal woman, I walked out the door and headed to Jamie's car, not really carrying anymore if any of my neighbors saw me. Besides, I figured that my transformation had been enough that most probably wouldn't even realize they were looking at me. Once in the car we kissed and then as Jamie was backing out she said, I've got to admit I'm excited about this, we're going to go get our first toy to share together. We've got a little time so maybe we will see a few other things that might spark our interest. When we walked in, we were politely and professionally greeted by a girl behind the counter and she asked us if we needed any help. Jamie said, No we're just looking for a few things to spice things up. The girl said, Take your time and if you have any questions, please don’t be uncomfortable, this is a no judgment zone, so please ask and I will be glad to help you any way I can. We both said Thank you and headed into the well-lit very clean store. I could see that there may have been a half a dozen other people shopping, a guy over there, a guy over here, a couple here and two girls over there. I was blown away how one huge entire wall held hundreds of dildos in various sizes, lengths and thicknesses. There were a couple that were so huge I couldn't imagine anybody being able to take them. They even had some you could fill up the balls with liquid and a little hand squeeze thingy that would make it squirt as if it was cumming. Next to them was a huge assortment of double dildos, same thing, all different lengths and thicknesses. After we discussed things we finally agreed and chose one and when Jamie pulled the package off the hook it was hanging on said, We need to get some lube while we are here. We looked around and saw a sign saying Massage Oils Etc so we headed over there and we were looking for the anal lube and saw that the male and female couple were standing in front of the lubes. As we got closer, we heard the woman say, I don't know honey that last stuff just really didn't seem to work very well or very long. In fact, I was kind of sore back there the next day. Jamie just calmly stepped up next to the lady and pulled one of the bottles from the shelf and turned to the lady and said, If I may suggest this one, I've tried several and this one I have found to be the best. Yes it's a little more expensive, but as the old saying goes, you get what you pay for. And then with the grin on her face and winking at them she whispered seductively, Besides this is edible also. Placing it in the woman's hands she grabbed two more bottles. As we turned to walk away she smiled at the couple and said, Good luck and enjoy. The woman smiled back at Jamie and then noticed the double dildo Jamie was holding and got a bigger smile as she thanked Jamie, looking back and forth at the two of us. Her husband was looking at us, obviously undressing both of us in his mind the way he kept looking us up and down. Just as we were walking away we heard the woman say, Wow she was pretty and did you see that double dong? The two of them are going to be having some awesome sex tonight.
Once we got in the car and started driving Jamie said there's some disinfectant wipes in the glove compartment. Open that baby up and make sure it's all sanitized before we play with it. After getting it out of the tight plastic packaging and holding it in my hand, wiping it off with the wipes, I felt like I was stroking a cock and was already starting to get excited. It must have shown because Jamie giggled and asked me if I was having a good time. I said, well I’m already imagining it, but I'm slightly unsure, did you have to pick one out so big? She replied you're just looking at the whole thing, just look at the half that you would be receiving. See I even picked one that had more of a narrow pointed head so it would slide inside easier and it really doesn't get that thick until near the center base. And look at that center base, it’s got all those nubby ends that will rub against you once you have your end all the way inside you. Once I looked at it in that perspective I was even more hornier now thinking about sharing it with her.
A moment later Jamie said, So Charles sent me a couple more instructions today and there's no problem with them. What he explained to me is that he gets off watching porn of real people doing things for their first time. It doesn't matter if it's a couple’s first time having sex together or a girls first time anal or two girls first time together or two guys first time, as long as it's real people and not paid actors. The way he wants it to be is that you and I have been friends for some time and I've always had the hots for you and finally bring you back to my place and get you half drunk and seduce you. He will be sitting in a chair off to the side so we just play it out and enjoy our acting together for his pleasure. I said, Okay just one little question, are we supposed to be women or are we supposed to be girls the way we are? She said you know good question, but I think he would probably want you to play as a female and me to play as who I am. He did say that one thing he wants me to do is when I think it's the right time in the seduction to pick up the remote control hit the power button and then play and they're will be some porn action and we take it from there.
We pulled into a driveway of just a regular looking house and she said, Okay I'm supposed to go in first, I guess to see if there's any last minute directions and then I will flash the outside light and then you come to the door cuz remember we're supposed to play this out as you coming to my place to visit. Then reaching and squeezing my hand she asked if I was ready to go thru with it. I took a calming breath and said okay. I watched her go inside and was waiting for the light and waited and waited and then the door opened and she walked back quickly to the car. I knew something was wrong she came up to the door and said, Now he wants to change things up slightly and I told him that any deviation other than already agreed, I would have to check with you first and it would be up to you and if you said No then that was my answer also and that we may just leave or continue with the original plan. I said, Okay so what is this deviation and why do you look worried. She took a deep breath and said, Because now he says he wants to fuck you. He wants to keep playing it out the way it had been planned but that now him and I are a couple and he walks in on us fucking and he convinces us to keep going and one of us may or may not suck him and then he wants to fuck you, but he promised he wouldn't come in you that he still wants myself and him to cum on your face. So it's up to you sweetie, we can tell him that no, that wasn't the plan at all and we leave and go back to your place and play with our toy together, or we can tell him no, we're sticking with the original plan, or yes you can finally experience another man fuck you and I will be right there with you. It's your call sweetie whatever you decide. I thought for a minute and then said, Well I guess maybe this is my chance to finally have sex with another man as long as you are comfortable with it. I looked at her and said, Boy I could sure use one of those drinks right now. She grinned and said, Well he does have a good bottle of bourbon whiskey there with two glasses and a nice bucket already. I thought about it for a moment and made up my mind and said, I think I'm willing to do it to, finally experience another man, as long as you will stay with us. Jamie smiled and said, I promise to be right there the whole time and I kind of had a feeling you would go through with it and if it helps I made him promise that if you did agree to it, he absolutely had to wear a condom. And I wouldn't worry about it too much because I think he's so hot for you that I don't think he will last too long. Then she said, Just sit tight, I'll be right back in one minute and she ran inside the house and then came right back out and handed me a glass that must have had at least three shots of whiskey in it over ice. She said, Here you go honey, enjoy this and then when you're ready, come on up to the door and it will just be you and I in the beginning as planned. He said that once we start fucking he will quietly and out the back and come back in through the front door and say that he got done early from having to work late when he walks in on us. Then she surprised me when she leaned in through the window and put her palm on my face and said, I love you Scott. She leaned in and kissed me and she said, Only if and when you are ready. I took about half of the drink down in two swallows as Jamie walked back inside. I suddenly knew I wanted to go through with this, to have sex with a man who only knew me as Lisa. I swallowed the last of the smooth whiskey and then looked in the visor mirror to make sure makeup and wig were all set and got out of the car and went up to the door.
Jamie instantly open the door and said, Hi Lisa I’m so glad that you could come by, it's been awhile since we've been able to hang out together, as she gave me a hug. I replied, Thank you Jamie, when you asked me if I wanted to get together I realized it's been a couple of months since we had hung out and did anything. You know works just been kind of crazy and everything, Life, you know what I mean. Before I knew it I had another glass of whiskey in my hand and we settled on the sofa and had make believe chit-chat, girl talk, when Jamie said, So I understand you and that guy, Mark or is it Marcus, have been together for a little while? I said, Yeah it's been about 4 months now. She grinned at me and said, So have you let him get into those panties yet? I exclaimed Jamie! She said, Oh come on Lisa you're a pretty girl and I know you’ve enjoyed sex or don't you remember last Christmas party. Well maybe you don't, you did have maybe a little bit too much drink but you confided in me of being horny and wanting a man. You even said you were probably going to go home and masturbate that night. I tried to blush and said, Oh my god did I say that? Jamie grinned and said Yes you did and I would have enjoyed being there to watch that. My head snapped up and said, What?! She didn't answer but refilled my drink quickly and said, Look I've been fighting a dilemma and I finally decided, so let me ask you this, have you ever been with another woman? I tried to act shocked/surprised and gasped, Are you asking what I think you're asking? I took another sip of my drink as if I was nervous. Jamie continued, Yes I'm asking have you ever been with another woman and touched and kissed and done things together? I tried to put on a shy face and asked Jamie, Why are you asking me these things? Jamie said, You answer my question and I'll answer yours. I tried to act sheepishly as I said, Well there was this time in college, after a party when my roommate and I went back to our room and we both had probably drank too much at the party and was talking about one of the guys and I guess we were both in a mood and we started kissing and then playing with each other's boobs. Jamie said but I can tell there was more right? I just nodded. Jamie said, Go on dear, I’d love to hear it. I reached for my glass and it was surprisingly empty and in a heartbeat Jamie refilled it and after taking a swallow and feeling the alcohol spreading inside me I said, Okay so we had been drinking we were kissing and playing with each other's boobs and we both admitted to being horny and we laid there in one bed side by side as we played with ourselves. Jamie asked, Did you enjoy doing that with her right beside you? I said, That the first time I don't think I really thought about it. She goes, Oh that first time? so there were times after that? I tried to blush again and said, Yeah there were a couple of other times where we would masturbate together. And Jamie continued, Did you two ever touch each other or masturbate each other or even lick each other's pussies? I took another drink and said, God I don't believe you're getting this out of me but yes the third time we were together we did touch each other's pussy and make each other cum. Jamie said, See that wasn't so bad now after all now was it Lisa? I said, No I guess not, I just never shared that with anybody. Jamie continued, I bet there have been times that you've thought back to that experience and you've masturbated about it haven't you? I said, Wait a minute, you said you would answer my question after I answered yours, which I did. Taking a big drink from her glass she took a deep breath and then said, Okay here's my dilemma I've been dealing with and I'm just going to come out and say it, I like you, I think your desirable and there are times when I masturbate thinking about you and I having sex together, there it is, I want you. So that's why I was asking if you had let him get inside your panties because if you hadn't and were sexually frustrated, then I want to help you take care of that. And honestly I'm so horny for you that I'm either going to masturbate if you get upset and leave, or I'm going to masturbate in front of you, or we can watch each other masturbate, or we can enjoy some girl/girl sex. Whatever you decide, One way or another I'm going to cum tonight. I said, I, oh, I, wow, oh wow, as I took another drink from my glass. Jamie said, Well since you didn't grab your stuff and run out of here, I'm guessing you're thinking about one of the options, so just relax and I'll let you make up your mind. She picked up the remote and turned on the TV on and on the screen is what looked like maybe a hotel room with two women about our age in nothing but bra and panties laying on a bed kissing. Soon the action increased as their clothes came off and their kisses were hotter and passionate as their hands were exploring each other. I was getting turned on and when I glanced over at Jamie, somehow she had miraculously removed her shirt and bra without me even noticing and she was cupping one boob playing with her nipple as her other hand was under her skirt rubbing herself. I guess she felt me looking at her because she glanced over at me and huskily said, Lisa I'm so fucking horny, I'm not going to stop. I said, I can't believe this is really happening and I can't believe that I don't want you to stop. And I really can’t believe you're actually turning me on. She grinned and said, Good just enjoy and if you want to touch yourself, you are safe here and by all means please do. As she got more comfortable I could see her legs open up wider as she was playing with herself under her skirt as she watched the screen. I finally reached under my skirt and started rubbing myself also. A moment later Jamie let out a little moan and quickly pulled her skirt off and I could plainly see she was hard in her panties as she kept rubbing herself with one hand and playing with her tit with the other. That did actually get me even more excited watching her. Then when the two girls on the screen started to take turns going down on each other, I unbuttoned and pulled off my blouse so that Jamie and Charles could see my white bustier as I started playing with my hard nipples. I turned my head slightly and could see that Charles was sitting in the chair, stroking himself as he watched and that kind of turned me on more when on the screen one of the girls started cumming from the other girl licking her pussy and clit. Jamie said, That's what I want to do to you Lisa, I want to lick your pussy and clit and make you cum, will you let me do that?
Somehow as hard as I felt I was, my clit was still tucked down in my panties and I wanted Jamie and I just looked at her and nodded. She moved to me and we started kissing as she pushed my skirt up to start rubbing me and I couldn't help but open my legs for her and she quickly had me freed of my panties as she caressed me. She
leaned in to me and whispered in my ear, he can make changes, so so will we, we aren't using the toys, we're saving them to use together back at your place when we are done here. Then she continued our scene as she said, I want your pussy Lisa. I want to lick your pussy and get you all wet. Do you want me to lick your pussy Lisa? I gasped, Oh my God I can't believe this is really happening, but yes yes I want to feel you licking me.
She very quickly had my skirt pulled off and I could see my reflection on the TV screen since whatever video had been playing had ended and now the screen was black. I could see myself in my white stockings, panties and bustier as Jamie, keeping my knees together, push them back to my chest and then pulling my panties to the side murmured, Oh what a pretty pink pussy you've got, even better than I had fantasized about. I'm going to lick this pretty pink pussy until you're begging to be fucked. She had me whimpering and moaning from what her tongue was doing to me. Soon I felt her finger starting to tease and then what must have been the lube and then her finger easing inside me making me gasp and moan, Oh my God Jamie I can’t believe this is happening, that I’m letting you do this to me. Quickly I could feel the warming action of the lube as she said, Oh my sweet Lisa your pussy just keeps getting hotter and wetter. I’ll stop if you want me to, but I don’t think you want me to, do you? I was squeezing my tits and moaned, yes, no, oh my god, no please don’t stop. After another minute Jamie huskily whispered, Do you want me inside you as much as I want to be inside you now? Can you handle a girl fucking you for your first time? I wasn't acting anymore as I whimpered and said, Yes yes please, I want to feel you inside me, I can’t believe this is really happening but yes oh God please do whatever you're going to do to me. Jamie said, I'm going to fuck your sweet hot pussy isn't that what you want? Can you say it, can you tell me you want to feel me inside you? I was whimpering and almost begging when I gasped, OH my God Jamie, I want to feel you pushing inside me, I want to feel you fucking me, I want to feel you fucking my pussy, please please put it inside me and fuck me now! I was squeezing one of my tits and clenching the edge of the sofa as she was kneeling and pressed against me, making me gasp and moan louder. I felt her slowly pushing inside me and then slowly deeper and deeper until she had completely filled me and just held herself inside me. She let out a natural little moan that it was either the scene we were acting out for Charles, who had now left the room already or it was because of the new version of the warming lube because she looked down at me and whispered that my pussy had never felt that hot to her before. My knees were practically touching my chest with her hands holding the back of my thighs keeping my legs pushed back and open as she slowly started working herself in and out of me and we were both really getting into it when the front door opened and Charles walked in. We both just froze with her hard clit half inside me as Charles said, Oh my God Jamie, Really? You think I'm going to work late so you're going to bring some girl home and fuck her? Then as he walked closer to us he said, Wait a minute this is that girl you’ve got pictures of on your phone that you've been so hot for isn't it? So you finally couldn't hold back and seduced her? Well good, go ahead and keep fucking her because the only time you're horny anymore is when you're thinking about her. Maybe once you’ve fucked her good you'll start thinking about this again, and he pulled his dick out. Looking at me he said, I've caught her several times masturbating, looking at your pictures on her phone. I can see why now, you are a hottie and look at how wet and pink your pussy is! He started undressing as he told Jamie, Go ahead keep fucking her because I know you have been wanting to. Now you've got that sweet pussy all hot and wet, just enjoy it because you two look so fucking hot like this, as he started stroking himself standing there watching us. Jamie started working in and out of me again. I could tell Jamie was really getting into it because she really started fucking me good making me whimper and moan over and over as Charles kept making comments about how hot it was watching us fuck. Somehow he had picked up Jamie's phone and was taking pictures and videos of us fucking, but I could see he was trying to get his dick in the edge of the pictures also. Then he said, Jamie I'll let you bring any girl home you want to fuck in the future, if you let me fuck this one with you now. Jamie looked down at me with that questioning look on her face and biting my bottom lip from what she was doing to me I just nodded. She turned to Charles and said, On three conditions, one, that you let me make her cum, two, you have to wear a condom and three, that if you do anything to hurt her, I will cut your dick off and make you eat it. And by the tone of her voice we both knew she was serious. He agreed and as he was putting on the condom Jamie pulled me down into the center of the sofa and we started 69ing and then I felt him get between my legs. I heard him say, God your pussy is so pretty pink and wet, like it's just asking to be fucked. I felt him rubbing his cock over my hole and then push inside me, making me moan on Jamie's clit in my mouth. Being as horny as we all had been leading up to this, it didn't take long from having another man's cock fucking me while Jamie sucked me as I sucked her and I knew I was getting close when Jamie pulled out of my mouth gasping saying oh my God Lisa you've got me right on the edge. I pushed up on Lisa's hips slightly and when her clit left my mouth I gasped out, Oh my God Jamie, I'm so close, I need to cum soon. Since Charles cock was a little smaller, not as thick as Jamie's, I was able to take the pounding he was giving me, and was actually enjoying it. Then he gasped out, Oh fuck oh fuck, your pussy is so hot on my cock. Make her cum, Jamie make her cum so I can feel it and watch her cumming with my cock inside her because I'm ready to give her mine. Jamie just bent down and took me back in her mouth and probably not 30 seconds later I felt it suddenly build inside me and I cried out, Oh my god, oh fuck, I'm going to cum and Jamie pulled her mouth off me and reached down to stroke me as I lost control and started cumming. Charles had his cock buried inside me, holding still as I was shaking and seeing stars as I was cumming and he groaned out, Holy fuck I can feel you cumming on my cock oh my God yes! Then I felt him pull out of me and moving beside Jamie, he pulled the condom off and he grabbed Jamie's clit as she grabbed his cock and they stroked each other, making each other cum, shooting their cum on my face as I held my mouth open for them. When they had both finished cumming, Charles kind of collapsed backwards. But Jamie scooted back and then leaned down to kiss me and licked some of the cum off my face when Charles said, Stop, wait a minute, let me get the camera because you two are so hot like that. He grabbed Jamie’s phone and said, Go ahead. Jamie continued to lick the cum off my face and then kiss me, feeding me the cum for another minute as Charles took pictures and videos. As Jamie finished and we were tenderly kissing we heard Charles say, Thank you so very much, that had to be one of the hottest times I've ever experienced. We looked over at him and he was holding out a warm wet washcloth to Jamie. She finished wiping me off and then we each got ourselves adjusted, tucked back down into our panties. Charles held out a fresh shot of whiskey for the two of us and said, I really do mean it, thank you very much for this. And then turning to Jamie he said, Would it be possible to send me a couple of pics or a video of tonight that you won't post just so I can have the memories of this night. Jamie agreed to this and we said our thank yous for the evening and we left.
On the way back my head was leaning back and my eyes were closed replaying everything in my mind when Jamie placed her hand on my thigh and said, Hey there are you okay? Are you bothered about what happened tonight, about another man fucking you? I opened my eyes and smiled and said, No I was fine with that, I was fine with everything, in fact being with you and having sex as Lisa and cumming with a cock inside me, I'm understanding more about you and myself. Jamie just said, that’s good and I guess it didn’t bother you having us cum on your face like that? I pretended to act shocked and said, us? Who else came on me? I was just so into seeing your hard clit above me, waiting for my reward, to watch you give me your cum. Jamie just whispered to me that the night wasn't over yet. I grinned at her and asked, Does that mean we get to go home and play with the toy we bought and haven't used yet? Jamie just grinned back and said, That's why I like you Lisa, because sometimes you can read my mind because I've been thinking about getting that cock in both of us and we fuck each other with it!