Lisa's Awakening, Chapter Sixteen
Scot & Jamie's Date Part 4

Something slowly woke me up from a deep sleep and I finally realized it was Jamie getting back into the bed with me, snuggling up against me. Unfortunately I also had to pee. She saw that I was waking up and leaned over and started kissing me and I told her to hold that thought I would be right back. When I crawled back in the bed with her under the warm blankets, pulling her back to me, I noticed she had removed her little nightie and only had on her panties. As we started to tenderly kiss with my caressing up and down her back to the top of her soft ass I whispered, I could have sworn, before I went to the bathroom you had more on than just these cute panties. She giggled and said, Well I didn't want my top to get in the way. In the way of what? I asked grinning at her. She gave me a deep passionate kiss as her hand slowly trailed down my chest across my stomach and down to grab and caress my dick and then said, Not in the way of what I hope will happen next. I glanced over at the little clock on the nightstand and seeing the time I pulled her tighter against me and said, Well I think we have a couple of hours for whatever might happen next.
Knowing we had this time together now and that in a few hours our date would be ending, I was planning on taking my time and enjoying every minute I could with her. Still holding each other tight our kisses were tender yet passionate as our hands solely caressed each other's body lightly touching and exploring eliciting soft little murmurs and moans from each other. She had one hand just very lightly caressing and stroking my hard dick and then would go down and fondle my balls and then tease that sensitive area between my ass and my balls and then go back up to lightly caress and stroke my dick some more. Then she started kissing my neck and moving down, kissing chest, lightly licked and playfully bit and kissed my nipples as she slowly traced her tongue down my chest. Pushing the blankets back kept slowly working down until she held my hard dick and started licking and kissing the head. Once she took me in her mouth I could tell she wanted to make this last also because she just slowly took her time with my hard dick in her mouth. It wasn't urgent cock sucking like it had been at times before, she was definitely enjoying what she was doing to me because I could hear her moan at times with my dick in her mouth and what she was doing to me was making me give out little moans from the pleasure she was giving me. I could feel her saliva running down on my balls and dripping and then when she slid her to hand down below my balls I just naturally spread and opened my legs more for her, letting out a soft guttural moan as she eased the finger inside my ass as she continued to slowly suck up and down on my cock. Finally b,efore it was getting too good I whispered, "Baby you have to stop that. She slipped her finger out of me and holding the shaft of my dick looked up at me with a pouty face and as she rubbed my dick back and forth over her cheeks and across her lips, she said, What's wrong am I not sucking your dick good enough, am I doing something wrong baby? I lightly laughed and said, You little vixen, you know damn well you're driving me crazy, no one's ever sucked my dick like you do, but it's not fair, you don't get to have all the fun. She grinned and said well let me have fun for just one more minute as she just started licking me from the tip of my dick all the way down, over my balls, to my ass and back up again along with little murmurs and kisses.
Finally I had to make her stop and pulled her back up to me and laying her back I started kissing down her neck and shoulders, taking my time, kissing and licking her tits and hard nipples and did the same to her by running my tongue slowly down her taught stomach till I reached the lacy band of her panties. I reached on each side of her, grabbing the waistband of her panties and pulled them down to her knees and with her knees still together pushed her legs back up towards her chest which made her clitty stick out between her thighs right at my open mouth. Doing to her what she did to me I took my time paying delicious attention to her hard clitty with my tongue before slowly pushing down to her pink rosebud. I wanted to take my time and explore and tease her and get her wetter before I eased the finger inside her. Unfortunately, when I did try, her muscle was clamped tight and refused to open and when I tried pushing a second time she gasped. She whispered, Scott please come up here and hold me a moment. I did and then she cupped my face with her hands and said, I’m sorry sweetie, I think all of the sex and lovemaking last night kind of wore me out back there, but I do want to feel you in me again. She continued, Remember what you said about openness and honesty? I said Yes. She continued, Okay I'm being open and honest with you, last night was the most intense pleasurable wonderful feeling I've ever experienced and you really did make me feel like a real woman. And now I really really want to make love even if I pretend that I'm a virgin giving it up to my lover the first time. I just want to feel us together as one. She looked at me hesitantly and said, I'm sorry was that too much? I kissed her again and said, Baby I don't think anything can be too much with you not even too much of a good time. If you want to continue I will and if you want me to stop I will. Her answer was to smile bigger and moved her hand down between us to grab my dick that was now only half hard and said, Yes I want us to continue and I don't want you to stop until you can't go anymore. But first we have to take care of this, as she started caressing and stroking my dick. Once she had me fully hard again she told me to kneal on the bed as she got the lube and came back and still stroking me got me all oiled up and I mean lube was practically dripping off me she had coated so much on my hard dick. She looked at me with such lust and desire on her face as she said, I don't want to wait any longer as she turned around on her hands and knees and presented her beautiful ass to me. I could see us in the mirror on the dresser top and had her move a little bit and pointing to the mirror explained, This way we can watch each other as she looked up and saw us in the mirror and said God that is so hot seeing us like that and seeing your hard glistening cock ready to be inside me. Now take the lube and coat me really good especially right on my entrance. Then softly but firmly slowly push inside of me, it will be very tight for a minute and then you will be able to push inside me more and when you are halfway in just stop and hold it there for me.
I did as she asked and she was very tight and seeing her bite her lower lip in the mirror I almost stopped when she moaned, Oh God, almost there, just push a little bit harder and then my head slowly started spreading her as it slowly pushed inside and when the entire head kind of popped inside her, I almost stopped as she cried, Oh fuck, and then, Don't you dare stop keep going a little more, until half of me was inside her and I stopped and held still. She was bent over with her forearms on the mattress with her forehead resting on them and she groaned out, So this is the feeling of the expression It Hurts So Good. After a moment or breathing, she relaxed slightly and said, Just hold still, and started working herrself back and forth a little bit on me, She really had felt like a true virgin when I first entered her and now that she was starting to work herself back and forth on me, I could feel her loosening up some, but she was still very tight which just seen to heighten it for me. I had one hand caressing and squeezing one of her ass cheeks while my other hand rubbed and caressed her back as she started using her hips a little more on me until she finally gasped as she pushed back and I was entirely deep inside her
She moaned out, Oh my God you just took my virginity! Well, you really didn't take it cuz I gave it to you freely. Now I want to feel us enjoying each other. Soon our bodies were working in rhythm together to give and receive pleasure to each other. And watching ourselves in the mirror just increased the intensity. I could see how hard she was bouncing each time our bodies came together. I pulled all the way out of her to put a little more lube on her bottom and my cock before pushing back inside her making her moan again. I reached around and down to grab her hard clitty and stroked it making her squeal in delight and she reached back with one hand practically digging her nails into my thigh. Then still on her knees, I grabbed her sides and pulled her up and back against me, my arms around her, one hand holding her clit and the around her cupping and squeezing her tits. She gave a guttural loan of pleasure and said, Oh my fucking god every time we're together I feel you hitting me in another spot inside me, God I can't believe what you make me feel.
We were trying to kiss in that position but it wasn't easy when she said, Watching us like this in the mirror is erotic, but I want to hold you and kiss you and look at your face as I feel you inside me. Lifting up and off my dick, she moved the pillow and laid back down on it, her hips arched up. spreading her legs and holding her arms up to me said, Come here baby. It only took seconds to sink down inside her making her moan deeper and she gasped out, Oh fuck Scott I just can't describe how this just feels so wonderful and so right with you. Don't be upset with this, but I sincerely hope that after having a surgery and getting a vagina, I will still feel the same way as I do now. I said, What's to be upset by that? and leaned down to kiss her and our kisses were so deep and passionate as our bodies move together and things were building in both of us as our lovemaking grew more passionate and intense. We could both feel the urgency building and she's arching her hips up against me, making her lube covered clitty slide up and down between our stomachs, just adding to it for her, making her gasp, Oh my god oh fuck yes Scott.
I was trying to stay in control for her by lessening my movements inside her when she grabbed me tight, her nails digging into my back and moaned, Oh my God Scott make us cum, I want I need to cum with you, I'm so close, please Scott make us cum together! Pushing inside her as far as I could go and leaning tightly on her, pushing my hands up underneath her back to her shoulders to hold her even tighter, kissing and biting her neck and shoulder as I started grinding inside her, making her hips gyrate against me, increasing the pleasure of her clitty rubbing between us. As per panting quickly got stronger and faster I pushed up a little to look down at her and our eyes locked together as she was biting her lip and just started nodding over and over urgently. Her hands were clenching the back of my waist, holding me in tight inside her as her hips were grinding against me and she started moaning louder and then was crying out, Oh my God Scott Oh my God Scott, I can't…I can't stop it and just cried out as her eyes practically rolled up into her head as her whole body just started quaking and shivering on me. Her muscles felt like they were gripping me and trying to pull me inside her even deeper and then I felt them spasming on me as she finally lost control and started cumming. That triggered it for me and we erupted together in explosive orgasms!
Even after our breathing had finally calmed down, we still lay there for several minutes holding each other and tenderly kissing until I felt myself slip out of her. I slid off to the side and pulled her tight against me. After a minute or two of holding/cuddling she said, Scott can I say something and ask you a question without you freaking out and running screaming from the room? I propped myself up on my elbow and look down at her and said, You really are a woman, you want to have deep conversations after sex. She had this hurtful look came over her face and I leaned down and kissed her and said, Relax baby, I'm only teasing. I meant that you are really a woman, but no it wasn't sex, it was wonderful beautiful love making we just shared. She smile and let out a little sigh and said, Well that's what I wanted to say. This is the second time with you, when it hasn't been sex, it has been beautiful lovemaking and I just never thought it would be possible. I’ve only dreamed that it may happen to me and now it has. I know this is new to both of us and really only our first date, if we call it that. But….but….and taking a deep breath blurted out, honestly I think I'm falling in love with you. Then she bit her lower lip and looked at me hesitantly to see how I would respond.
I knew we were at a very important place, the two of us, and I was thinking about what she said and the feelings I was experiencing and knew that whatever was said in the next couple of minutes was going to make a difference. She let out her breath and said, Well at least you didn't run screaming from the room, but you're not saying anything. I pulled her tight against me and gave her a long hard deep kiss and when I pulled back I said, Yes absolutely, it was beautiful passionate love making that we shared together and I want it to happen more and more going forward. And yes, I am definitely falling for you and want to be a part of your life. She asked, Even after I have the surgery? I said absolutely, that's not going to change anything about how I feel for you. She smiled and reached up and pulled my head down and kissed me and said, That's good enough for now. I just want you to know how comfortable I am with you, of how safe I feel with you. Can we just lay here for a bit and hold each other and talk? There's some things I want to tell you. I scooted back down and pulled her to me and she again had her head resting on my shoulder with her hand on my chest and she began, I have not taken this decision to have the surgery lightly. I've done an awful lot of research and did my own interviews. I spoke with several doctors and the one I finally chose, who made me feel comfortable, is ranked as one of the tops in his field. Once every 6 months, I fly out to the coast for my appointments with him and when it's time, to reduce my traveling, he will fly out here and do that surgery and the other boob doctor will do my boobs while I'm still under anesthesia. Don't take this the wrong way but I'm spending an awful lot of money to do this because I feel that I won't feel complete as a person, as a woman, until I do this. Now of course I've had questions about the sex act after the surgery and my doctor was very helpful and got in touch with some of his other clients and gave them my information and I have spoken with three other women that were grateful for the doctor and they all described everything the exact way that I feel.
She took a breath for a moment and then continued on, All three of them did tell me that once they felt that they were healed and the doctor gave them medical permission, they were all curious to find out and experience vaginal sex as a woman. All three of them said it was good but that they did not come every time. I've heard women say that they've had sex and a guy will come and they won't all the time. But with the three that I talked to, they said that if they or their partner did pay attention and play with their clit, then they could come. That even though they no longer had a full penis, the base of the penis and all of the nerves were still intact and made into a clitty. She stopped there and I could tell she was still thinking and things were running through her head when she hesitantly asked, I don't know how to ask this but do you really think we've got something together and can still be a couple after I have the surgery? I could see how scared and nervous and vulnerable she was feeling. I just held her tighter and realized how much I did care for her. Isaid, Yes I do, I do not have any plans to run away from you because you will have the surgery. I am falling for you as the woman that I know and care about and the surgery is not going to matter to me. She said, Even if I get grumpy or don't feel right? I asked her what she meant? She said, Well all three of the girls did say that at one point they went through a bit of depression because of not having a penis and balls anymore,e even though two of them said they were thankful it was gone it was still just the mind causing them to feel that way. One of them told me in confidence that she had a really difficult time in the beginning after her surgery before she experienced sex as a woman because she really enjoyed threesomes of fucking one while another fucked her but then admitted that after she had had sex a couple of times and could enjoy it as a woman and come from her clit she finally accepted it and then she discovered something else. She told me that as we have a male body, with a prostate gland, that stays intact, even after the surgery and still functions. She said that what she loves now is sex with two guys, double penetrating her, so she has a cock in her ass and another in her pussy. And that playing with her clit with two dicks in her, she says now she comes harder than she ever did before. All I could really think of saying was just wow. She giggled against me and said, Yeah I thought that too, especially when she told me that once she discovered that about herself, that she's turned into a slut and has sex with at least two guys almost every weekend. She said she doesn't regret it one bit and is trying to make up for lost time of not being a real woman.
Having us laying tight together the way we were I could feel that her nipples had hardened. I pulled back slightly and flicked my finger across one and teasingly said, That seemed to kind of excite you huh? She turned bright red blushing and said kind of bashfully, Okay I admit it it did sound erotic before, but after listening to her describe it and making love to you with just my ass and no pussy and imagining having 2 cocks inside me, okay, I admit it, the thought does turn me on. But quickly added, But I couldn't go through with it on my own and would only try it with you and somebody we were both comfortable with. I grinned and asked, Are you thinking of Aaron? She responded, To be honest, I havn't even thought about Aaron since I've been with you, but yeah, I think if you were okay with it I would be willing to do it with you and him.
Then she got this distant far away look in her eyes and after just over a minute of her not saying anything I was wondering if something was wrong and I whispered hey Earth to Jamie? After a moment she blinked and looked at me and I said, Where did you go? Her answer was to set up and look me dead in the eye and asked, I have to know this 100% are you will you be with me as I go through all of this? Still looking at her and not blinking, I said, I promise I will be with you up to the surgery, I will be at the hospital for you in the surgery and hopefully I will be with you for a long long time after the surgery. She whispered, Please promise me, please don't hurt me. I took her hand and placing it on my chest and said, I give you my heart because you’ve already taken it, I promise! She gave a little laugh and said, Well if you do hurt me then I will use a knife and I will perform my own male to female surgery on you, if you catch my drift. I knew she was trying to lighten the mood a little, but I said, Jamie Honey, you have my word, and pulled her down to kiss her. After we kissed for a minute she pulled back and then blurted out, I don't want to wait, I want to move my surgery up now, I don't want to wait any longer to become a woman and I want to be your woman! I think she kind of surprised herself by blurting that out because she froze and had the look of a deer caught in a car's headlights. I had to let her know it was okay, so I started to get off the bed and said, Okay let's get your stuff together and get out of here and go to the hospital. She laughed and slapped me and called me an ass to which I replied yes I have one and you love it and it's yours as much as my heart is yours. But how can you move up the surgery I thought it wasn't scheduled for a couple of more years? She said, Well the doctor and I just had a tentative date scheduled, but he said that when I was finally ready, to give him 4 months notice so he could make all of the proper arrangements with paperwork and a hospital room and nursing assistance etc etc. So if you really are with me, I'm thinking to see if he can do it in 6 months, the anniversary of the first time we made love. I sai,I am flattered by that and I told you I am here for you and if this is what you want, then call your doctor tomorrow. She looked at me with disbelief and said, Really? I smiled at her and said absolutely. She practically threw herself on me and was just give me fast kisses all over my face saying, thank you, thank you, thank you, you just keep making me the happiest girl over and over and over again.

To some of you following this story, I know you may not like how this is going, but don't worry, Lisa is most definitely still here and ready.