Journal of a journey - Book #144

I'm not sure where to start this other than to say that it's now the new year and that we have moved ahead with her desire to be his sexually. My brain is still all over the place, especially after last night with her and our ‘celebration’ of seeing in the new year.

I guess it might be easier to go chronologically as best as possible. I know that she knew I was anxious on Sunday (New Year's Eve) and she tried to calm me down but at the same time, I know she was coaching me and not so much calming me down but more getting me to accept everything and trying to be calm about it. She said several times that she wanted to make it as real as possible and that it meant a lot to her not to have to think otherwise. I understood what she meant, and I told her that I would be there for her and would go along with whatever she thought would be best.

So, by the time we were getting down to having some fun, I had already begun to have it sink in that I should enjoy as much as I can out of the night and, as I'd shared before, not think too far ahead.

I guess it must have been about 7 pm or so when we found ourselves up in the bedroom and after kissing and getting hot with each other she giggled and asked me quite calmly, "Want to use the first one now?" to which I replied by pulling her towards me and passionately kissing her. She'd said she wanted to take things slowly and we did.

I undressed first and then as I sat at the edge of the bed, she slowly did a striptease for me. She lingered in her bra and panties for a bit, and I told her I loved how she looked like that. She said that my cock made it kind of obvious!

She took off her bra first and dangled her breasts over me, but it was when she slid off her panties that it sort of brought me back to reality when I saw she had more than a ‘5-o'clock-shadow’ down there and that a lot of her pubes had grown in. It had been soooo long since I'd seen her with hair there, that it got to me.

I think she knew and she lay down next to me and we got close, ‘skin-to-skin’ as she put it, kissed me and asked me if I was turned on. I told her I was, about a lot of things. I can't recall exactly what we said now but she told me she loved me and loved me even more for what I was going to let her do and go along with. I told her how horny I was and how I needed her.

She giggled, touched my cock, and said, “That’s quite obvious!”

We played a lot during foreplay; she sucked my cock as I fingered her; we 69'ed; she sat back against the headboard at one point and let me see all of her. She asked/made me 'use all the right words' as she asked me to tell her calmly about what I was going to give to Paul. It took me a while to get to what she wanted me to say but eventually, I said, "I'm going to tell Paul that your vagina is now his to use". She moaned softly as I told her that, but she moaned even louder when I said, "And I'm going to tell him that he can shave you bare again".

I recall that I told her it hurt to say that to her but at the same time, it gave me the most intense sexual chill and strange pleasure. She kissed me passionately again and then just said, "Thank you so much. I love you".

I don't know how long we were at this but eventually, we both needed more. She would suck my cock and tell me how sweet the pre-cum tasted and giggled that she knew I was horny. Her pussy felt wetter and wetter the longer we played with each other, the hair closest to her slit was wet and slicked back leaving her looking much more *******. When I'd rub at her clit, I could see her pussy spasming open and closed so just as she knew I was close, I knew what she needed.

I went to put the condom on, but she took it from me and said she wanted to do it these last two times. I nearly came in her hand as she held my cock and rolled it down over it. I had to hold back again when she lay back and guided me into her waiting pussy. She was sooo warm and sooo wet inside that once the head of my cock was in her, the rest slid in effortlessly.

She wrapped her legs around behind me and told me to stay still in her as we hugged and kissed; it'd been a long time since I felt her that passionate with me. She then wiggled her butt to slide my cock further into her but still held me in place not letting me thrust just yet.

Kissing her while still deep inside her was very erotic and also something we hadn't done in a very long time. However just as we ended our kiss, she teased me and said, "Paul and I do this", which she knew would get me hard and get me going! And did it ever; my cock was throbbing when she released her legs and let me start fucking her.

I'd like to say our first time took a long time, but it didn't. She'd cum pretty intensely a few times during foreplay and, yes, I could feel her body tense and spasm as she held me in her once we both got into the motion. It was just a few minutes later when I told her I was getting close and she told me lovingly that I should enjoy it, that, "we can take even longer next time." With that, she lay back, pulled her legs apart for me, and made it obvious that I should enjoy myself. I pounded at her for a few minutes before thrusting into her frantically.

She must have known the moment I'd cum because not a split second afterward she had her arms around me hugging me tightly and cooing in my ear, "Come on honey, give it to me" and it felt like the top of my head came off when I finally let go.

The next thing I remember is pushing myself up off her and feeling her hand slither down to my softening cock so she could hold the condom as I slid out of her.

I lay back on the bed next to her afterward and she moved up onto her elbow when I opened my eyes she was holding the condom in front of me saying, "Wow, this must be getting to you baby.... this is a LOT of cum!" and she just put it on the nightstand.

We kissed and lay there for a little, while she would gently stroke my softened cock and giggle as she kept pulling out more and more drips of cum. She brought her finger up to our mouths when we were kissing which I thought was pretty erotic.


We lay there together for a bit longer and she again thanked me for being okay with everything. I told her honestly, at that point in the night at least, that I was still good with everything. She giggled and held my cock and teased me, "Is he (meaning my cock) going to be up for more fun at midnight?"

When I nodded, she smiled and hugged me and then had what looked to me like an almost evil grin on her face when she asked, “Wanna take a lick?"

As I moved down it started to get to me; when I came face to face with her pussy it hit me what I was giving up. Maybe having just cum kind of dampened down my ardor. I mean, I wanted to lick her (and I did) she was incredibly sweet with the faint taste of a condom mixed in but as I licked her it started to get to me, and I guess she knew it. She pulled my head up, looked at me, and said, "You don't have to if you don't want to".

I told her it wasn't that and she just said, "Relax about it, okay honey, and let’s enjoy ourselves".

She slid down the bed a bit and pushed her pussy up to me and I took a deep breath and took a moment and a good close look. Her pubes were still bushy up on top but the sides and bottom around her pussy were now all damp and flattened down leaving her fully on display. She smiled when she saw my expression and pulled her knees back and it opened up as I watched. I slid my tongue in and tasted just how much she'd cum, it was soooo sweet.

I was just starting to get into it and beginning to enjoy myself when she put her hand on my head and said, "That's enough baby" and pushed me away. I sat back up and looked at her. She looked so beautiful, especially now that I'd made her pussy even wetter.

I don't remember all we talked about as I sat there looking at her. I do remember when headed back downstairs for some food, that I felt a whole lot better about things.

She asked me what I'd like to see her in for the rest of the night in terms of lingerie. I was tempted to ask to see her in something that she normally only wears when Paul is there but instead, I told her that I would love to see her wearing something like white lacy panties, a black garter belt, black stockings, and her sexy see-through camisole.

She smiled and asked, "Anything else?"

I bit my tongue at first but then said I'd like her to put one of my dress shirts on over it.

She went to her closet held up each item and asked me if I was okay with what she'd picked then asked me why I wanted her to wear panties. I told her that I wanted to be able to take them off her one last time. She blushed at what I said and hugged me and kissed me and then just said, "Okay," and as she pulled them up, she told me she loved me.

She pulled the garter belt over the panties and then the stockings. I was still naked, and I got hard as I watched her clip the stockings to the garter belt. As she pulled on the top she smiled and said, "You're going to want to watch me get dressed more aren't you?"

I just nodded; she knew I would.

We ate some food (we had a bunch of different appetizer things to cook throughout the night) and drank a bit. We brought our drinks down to the den and put the TV on. While we watched we got closer and cozier and all of that.

The whole time she kept up a certain level of teasing including reminding me a few times of, "Remember when Paul ..... on this couch" or ".... while you watched us in here...". She loved that I got hard as we lay there, and she gently stroked my cock as I unbuttoned the shirt she was wearing and started to play with her breasts.

Now all this took place over an hour or two as we just lay there with each other. Sometimes I would go and get us another drink or sometimes she would. Eventually, she left my shirt off and dropped it to the floor and I loved seeing her breasts beneath the sheer top and feeling them. As we kissed, I put my hand into her panties and after teasing her a bit, I slid my fingers into her and gently finger-fucked her as we lay together watching TV.

At one point she turned her head to me and asked me if I wanted to slide her panty to the side and, "... feel me again...". I told her that the condom was upstairs, and she smiled and reached into the pocket on my shirt on the floor and handed me a foil packet. Before she put it in my hand, she asked, "Or do you want to feel me bare?"

When it took me a second to answer, she knew exactly what she was doing. I think she would have let me if I'd said yes, but I couldn't bring myself to say it. Instead, I answered by just taking the packet from her hand and opening it.

As I put it on, she smiled and said, "I thought so...." and before I could say anything else she said softly, "If you want to know, I would rather you used one".

I moaned out loud and said something about ‘not being ready yet’.

She smiled and said, "There's one more upstairs …" then added, "… you can choose which one you want to fill" and laughed as she said, "I just want you in me right now".

When she saw me roll it down my hard cock I watched as she wet her fingers in her mouth and started to play with herself a bit. A second later she rolled over on the couch putting her back to me again and with her one hand, guided my hard cock into her. She didn't move and the way she laid against me made it obvious she wanted me to be still.

It was amazingly erotic lying there with my cock in her and just watching TV; it had been so long since we'd done something like this that I just loved it. At a commercial, she turned her head to me and said so nonchalantly that I knew she meant it as a tease, "Paul and I do this all the time." With that, she turned back towards the TV and snuggled back up against me taking me deeper in her.

In the next few minutes, it got to me, thinking of him in her like that and yes, him bare and likely her wet from him. I just found myself feeling torn in half, part of me was increasingly anxious, and another part of me getting into it and thinking about it.

It didn't matter, all too soon the TV show ended and it felt just so amazing to simply feel her just get up from the couch and simply pull off me. She smiled as my cock still throbbed to see that I had filled the condom, and she teased me that we should start getting ready for later. It was only about 10 pm or so and I was confused till she said that we would come back down for a little while, watch the ball drop on TV, and we would then go upstairs for the ending of our night.

Upstairs she had a bunch of candles that she wanted to put in our bedroom and she'd picked out some music she'd like as background. She also showed me the condom waiting for me.

We stood next to our bed and kissed for a bit before getting dressed; she was so sexy. She asked me why I'd had her wear panties, and I told her that I wanted to get used to how it would be. She smiled and said that she had wondered if it might be easier for me if she did that, and wore panties more for a while.

We got out the champagne and as we went back down to the den, I saw that it was already almost 11:30 pm. She giggled to see the bulge in my pants and that I was hard again. She unzipped me and asked me to help her put the condom back on while we lay on the couch. I did so and, sure enough, a moment later she lifted one of her legs and as if it were nothing, she didn't even turn her head back to me, she slid my cock back into her now very wet pussy.

This time we fucked gently and slowly. I could feel that since I'd cum earlier, that it was going to take more than that to get me off again. Instead, knowing that she enjoys me feeling her, we pulled her panties to one side and I had one hand under her top while the other held me up and I managed to play with her pubic hair. I could feel it when she'd put her fingers down to her pussy and began to rub a bit and became even wetter as she'd run them around, up and down my cock. I was getting horny as I thought of her doing this with Paul.

When it was 11:55 pm she again slid herself off my cock and sat up next to me. We had some champagne ready for a toast and as the ball dropped and it became ‘next year’ we kissed and shared our love for each other. I told her that I hoped the new year would be everything she wanted it to be.

She smiled and said the same and then she got a sexy look and said, "Do you think it's time?"


We brought a glass of champagne each up to the bedroom and lit the candles and we spent a lot of time hugging and kissing. She asked me if we could talk and tease about 'it' and I said yes. We lay on the bed next to each other and I told her how turned on I was, also how nervous I was. She confided that despite her seeming to be calm, she was a bundle of nerves too.

She asked me again if I was ready and I told her that I was. She asked me to stand next to the bed and when I did, she stood up and said she wanted to undress me to have sex with me for the last time. I moaned softly but was so turned on, it was hard to be anything other than horny. She kissed my chest and held me tightly as she sat back on the bed and looked up at me.

A moment later she just said, "Okay" and with that, she slid off my lounge-pants leaving me in just a sexier pair of boxers. My cock peeked out of the open fly and she giggled and said that it looked like I was more eager than I had said. She leaned in and licked the head of my cock before pulling my boxers off, commenting on liking me naked. Without saying a word, she reached out and put her hand behind me pulled me to her, and, telling me to stand still and enjoy, took me into her mouth and went back to work on me.

My god was I hard, even after cumming once already. When I felt significantly harder she pulled off again and said, "There, that's better" and sat back and smiled. She looked up at me and said softly, "I'm ready... I can't believe I’m saying this but I'm ready for this....”. A moment later she stood up and pushed me onto the bed and said, "My turn now".

She looked amazing in the candlelight. She looked at me and said, "You do it". I took great delight in unclipping her stockings from her garter belt and then sliding it off her leaving her standing in just panties, the top, and her stockings.

I stood up pulled her hands up and raised her arms in the air to slide the top off. While I had her arms up, I pulled her naked body to me against my chest, kissed and held her for a second - it felt good to have one last time to do something like that. She remained standing in front of me as I sat down and I then slowly rolled down her stockings which she stepped out of one, then the other.

I could see her pubes through the lacy panties, and she asked me if I was going to take them off. I pulled her down next to me and hugged and kissed her and told her that I needed to take more time. She didn't understand until I said I needed more time before I took them off her for what may be the last time. She was touched by what I'd said, and she even realized that she was rushing things. I told her I loved her in just her panties and thought that maybe I could see her more in them. She looked at me and said, "Mmmm, instead of me naked?" to which I just moaned yes softly.

We lay together for a while and she gently stroked my cock while teasing me about how ‘hard I am for her’. More and more she began to talk about the 'last time', feeling it; doing it; feeling her; thrusting. She went on and I can't even begin to describe how hot it was to hear her and yet only be touching her on the outside of her panties. I felt down between her legs and the crotch was positively wet and her inner thighs felt moist! She told me I should take them off so, "you can see my vagina for as long as you want to". I didn't miss the implication (not sure there was one but in my head, there was).

I told her I loved her in white panties, and she smiled and said she wanted to wear them again for Paul the next day. It was like everything she and I said just played and fitted well with each other. I fought off the bad thoughts and decided to simply go with it. Then she stood up and finally said to me that I should strip her.

It didn't feel real at first but when I touched her panties it felt so amazing. I felt so torn, as if not pulling them down would somehow make it different but at the same time, I don't know how to explain it other than to say that it just felt like what I needed to do; it didn't seem like a question of wanting to do it, it just became something I had to do.

(I'm hard again now as I type this even with how I feel, it feels so good to re-live it.)

I started to pull them down and it felt amazing to be doing this. The candlelight in the room gave her skin this amazing warm glow; it was warm in the room and I could almost feel her warm skin radiating through the panties. She smiled as I pulled them down, deliberately slowly and, oh god, do I remember how it felt. Her hips appeared first and a bit further and the top of her curly pubes appeared, and I caught my breath to see it. But as I pulled them further, I started to get anxious. She must have sensed my anxiety and that, I didn't, couldn't, look up at her. As I held still, she put her hand on my shoulder and that just seemed to be what I needed. I slid them down further and a moment later the top of her pussy appeared with her panties just covering her clit but with the hood part visible and I felt my cock start to throb. It surprised me that I was as turned on as I began to feel more relaxed and that I didn't feel the bad stuff.

I looked up at her and smiled; she smiled back and said, "Take as long as you need honey ...." and gently squeezed my shoulder.

I thought that time had stood still (she later told me that it hadn't) but it felt like it took forever to slide her panties further down. Then the desire to see her finally took me over and I slid them down further. She told me later that she saw my cock start to leak as I slid her panties fully down to where they simply fell to the floor and pooled around her ankles.

Seeing her pussy so close was beautiful and when she stepped out of her panties, I swore she deliberately did it in slow motion too (but she said she didn't) and it was an amazing tease to see her swollen lips so clearly as she stepped aside. My cock was rock hard by the time she lay in bed next to me and we started kissing again.

She held my cock in her hand, and said in a teasing but also loving way, "I want to suck it for a while ... you know... get and keep you good and hard for our last time....".

I groaned out loud as she held my cock and then again as she leaned down and started to suck it. She knew me well and looked up at me and said, "Besides, this will help you go for seconds" and again sucked my cock into her mouth, only this time, adding a few other things like her knuckles on the underside of my crotch and also to her teasing my butt a tiny bit with her fist. My cock throbbed in her mouth, but I knew I wasn't close to cumming.

Her mouth felt amazing but again I have no concept of time here other than what seemed like a few minutes later when I felt her suck her mouth off the tip of my rock-hard cock and it was all wet from her mouth. She looked up at me and asked me, "Do you want more?", didn’t wait for an answer before she took it in again for a quick deep suck, pulled it out again, and added, " … or are you ready for other things?"

I told her I was getting close and she smiled, stroked my cock and said, "I know you're excited baby...." and she started to get into stroking me, leaning down to suck and lick at the head every few strokes. She said other stuff, like telling me to, " .. be sure and wait for the condom honey..." and, " … we want this last time to be really good baby".

Hearing her say ‘last time’ over and over got to me. I know it's not something I should have wanted and yet, lying there with her sucking me as she was, it was hard to want anything other than more!

She reached over to the nightstand picked up the last remaining foil-wrapped condom and asked, "Do you want to put it on or should I?" I didn’t answer so she got up closer to me on her side and repeated, " …. do you want to put the last one on baby, or should I?”

I guess my eyes got a bit watery because without saying anything she leaned in and kissed me passionately and then pulled back and said, "Is it what you want?"

When I didn't say anything right away she said, "I don't want to hurt you by saying this but I think it's time honey" and then she said, "... it is what I would like a baby".

Without saying anything I took the foil package from her hand. She smiled, leaned in kissed me, and said, "Thank you, honey..... it's going to be okay baby..... you'll see... " After a short pause she added, ".... I want this....".

I tore open the foil and rolled the condom down over my throbbing cock. She looked down and saw that I had it on all the way she looked up at me and said, "It's time honey". I lay there on my back with my hard cock erect as can be.

She kissed me and before doing anything else she handed me my glass of champagne and told me, "Let’s have a sip first". A moment later she lay back and spread her legs for me.

I never got soft even though I felt this wave of fear as I looked at her. I told her that she looked so hot; her pussy looked so hot and she looked at me and said, "Use the right words baby... tell me... what do you want....". She knew it, the word ‘vagina’ just does it to me, even reading it by me or hearing it said by others, it just gives me this weird sexy feeling. So I told her, "I want your vagina one last time baby".

What more can I say about the’ last time’ other than it being intense Whatever we said as we began and whatever she teased me with, I know I heard her but at the same time, it just didn't seem to register in my memory. Honestly, the moment the head of my cock penetrated her, knowing she wanted to play and act out that it was the start of my last time in her, it was so overwhelming.

I felt the condom squeezing my shaft and I actually had a fleeting thought of taking it off, yet the thought that I wasn't going to cum in her this last time simply consumed me. I felt myself trying to fight off the feelings and urges despite how I was feeling, deeper and deeper she wanted me. I pushed hard into her until I felt her curly pubes mingle with mine.

At one point she pushed me out of her, turned over onto her knees, and told me to, "fuck me hard". As I held her hips, she teased me, "Tell me what you see" and I knew she wanted me to use the right words. I told her that her vagina looked amazing all wet and open and that her clit looked so swollen; I told her it looked like she needed to cum again.

She hissed back that I'd better fuck her while she still wanted me to!

She looked amazing, I reached down and held her open and spent time looking at her from that angle, wanting to take a good look at her. Everything was open to my view and knowing her open vagina was going to be only for Paul some 12 hours later got to me. I pushed my rock-hard cock into her and she squealed; I fucked her hard like she wanted.

She again teased me to enjoy her while I still could but we both knew how our last time needed to end. She came deep and hard on her knees as I gave her a few gentle swats on her ass to help her along. But, for me, there was no way she would be in any other position than a missionary to share with me my last time. I pulled out and she obligingly turned over onto her back and spread her legs.

I tried, oh I tried so hard to hold off as long as I could. Whatever she was saying to me, if I wasn't on the edge already, she'd now brought me back to my full horniness that surprised even me. But in the end, the feelings and the mental knowledge were just too much for me and she knew that I couldn't hold back any longer. She pulled me into her again and with her legs around my back she screamed at me to, "fuck me hard …. make me cum one last time" and, Oh, did she cum!!!

Wow, the feeling of her gushing wet beneath me, as I ejaculated spurt after spurt into the condom, was just amazing. I tried to hold off but, in the end, I couldn't. She felt amazing; I felt amazing; it was just amazing.

I stayed hard for a while, and she squealed as she came even harder like she has so many times but in the end, she wrapped her arms and legs around me and pulled me close. We shared kisses that again, I thought, lasted forever. She told me she loved me and then she said it; she looked up at me and said, "Let me hold it honey while you pull out" as I leaned back and she reached for my cock and condom and held me still and in-place and said softly, "okay baby.... pull out slowly please....".

I wish it all would have taken so much longer but it didn’t, and I knew it had to come to an end. I know that my eyes were teary as I felt myself start to slip out of her but what surprised me was seeing her reach up to wipe her own eyes as I pulled out of her. She didn't look at me, instead, she pulled me close and held me, our heads next to each other, ears touching and she just held me tightly with one arm and somehow managed a moment later to hold the condom in her other hand. She kissed me and then sat back and showed me the condom and giggled, "That's a lot for you for your first time baby much less a second!"

She put it on the nightstand and again pulled me close to her and hugged me tightly. She kissed me without saying anything else and then said, "It'll be okay baby, you will be okay?".

I hugged her back, and as I was still so up from the awesome orgasm that I gave it no thought that it was the last time I told her, “Yeah, I think it will be ... we'll see...". I guess from how I sounded she figured I was okay.


Honestly, there wasn't a lot more between us on New Year’s Eve. We slept naked together, I told her that it turned me on; she giggled and said she sleeps that way with Paul then turned to me and said that we ‘probably shouldn't be doing this through’. She then smiled and said that this one night would be okay and giggled, "… it's not like you're going to be able to cum a 3rd time".

I remember as we lay there that I thought there would have been more to how I would have felt looking back at the night and it surprised me that I was as relatively calm and even happy as I was.


I tried to sleep but I couldn't. Writing all of that earlier has me back on edge. I stopped there because things weren't quite as content come Monday. I would prefer to come back at another point and share what happened when we came to the next morning. Anyway, that’s this book filled and I need to go find a fresh one before I can write about that.