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Like most other people on our planet I have to go grocery shopping from time to time. It just has do be done. Not that I love doing it, but well, one thing that I like even less is starving. Or running out of snacks while hanging out in front of my TV.

To prevent such accidents from happening I headed into the grocery store not far away from the place I was living in. About two times a week, sometimes even three. Because stupid me tends to forget buying non important stuff like canned tomatoes when planing to cook some pasta with tomato sauce.

I normally go grocery shopping on Tuesday and Fridays, all the time after work. I take a enormous bag with me and on my way home I get some food supplies. But when I am on vacation, or when I have days off, I do my shopping in the late morning hours. Because there are by far less people are in the store and it makes grocery shopping a much more relaxing experience.

One day, I had a day off, thirty three year old me was standing in front of the pasta shelf, she came around the corner. She caught my eyes within a moment or two. She looked beautiful and her about twenty four year old body was to die for. She made my jaw dropping to the ground. I lost it. I was standing there, starring at her while probably looking like a total moron.

She saw what was going on with me. And no, she wasn’t laughing at me. Or pointing with her finger at me. She just smiled at me. After some time trying to get my shit together I smiled back.

But that was all that happened when I first ran into her. Because when I was myself enough again to come up with the grand idea to talk to her, to initiate a conversation, she had already left the store. I was frozen solid for a couple of minutes. And yes, I missed the chance to talk with her.

Back at home I was feeling like punching myself in the face for missing that damn chance. She really was my type. And she was more or less every woman I could think off after I ran into her for the first time. Damn it, it was love on the first sight for me.

After about two weeks hating myself for the error I made I began to think straight. I analyzed the hole situation. I came up with a conclusion, a feasible solution for my issue: I was assuming that she was living in the area. I also assumed that she was like me, or many other people and that she went grocery shopping at some fixed days, probably even at a fixed time every week. So I came up with the big plan to head grocery shopping around the time when I first ran into her.

So far, so good. I had a plan. I just had to convince my boss that I needed time off every Tuesday morning. That I would show up for work about noon. At first I was thinking about making up something like I had to go to therapy every Tuesday morning. Or that I had to be at home because who knows what.

In the end I did something by far more brave. I told my boss the ugly truth. I told her about the woman I ran into, I told her about my feelings and I told her about my plan. To my surprise, she had some understanding for my case. And she gave me Tuesday morning off, but I had to work in the time. I nearly hugged her when she supported my plan.

From that week on I went grocery shopping every Tuesday morning. Before I went to work I spent a couple of hours in the grocery store. I had no luck on my first Tuesday, but on my second one she showed up again. The same thing like when I ran into her for the first time happened. Another chance missed.

But I wasn’t giving up. I staid at it. The sixth approach was the final and successful one. I was able to approach her and get a couple of words out. My doing put a enormous smile on her face. Then we talked. We had some chit chat up and running. To my surprise she had a really deep voice, but well, there are worse things out there, like forgetting to ask her for number. Yes, I pulled that stunt.

Luckily I ran into her again on Tuesday morning exactly two weeks later. We once more had a conversation up and running, but this time I got her number. I also told her that I would contact her soon. And that I’d love to ask her out for a date. Hearing me saying the last thing put a enormous smile on her face.

On Friday night we went out on our first date together. I picked a classic, some nice Italian food. Because who doesn’t like their pasta or pizza. I picked her up in front of her place, then we walked towards the restaurant together. On our walk we talked about the neighborhood we were living in. And doing so slowly but steadily broke the ice.

We had a few laughs while we enjoyed our food. Luckily we found some common ground to talk about. The whole evening was more than just a relaxing thing. And on the attraction site, we constantly were checking each other out. We clearly had caught each other’s eye. Something was in the making.

But not on that day. We went back home together, while still talking, while enjoying the nightly city and while still getting to know each other. When we arrived in front of her house we hugged, we wished each other a good night and then she went upstairs and I went back home.

And looking back from now, it was the right thing to do. Hooking up for sure wouldn’t have been the right thing to do. But we staid in contact. We texted more than just a lot back then. And we went on our second date on the following Sunday afternoon. We clearly wasted no time.

We went to the movies together. We both enjoyed the film. We got touchy while sitting in the cinema. The gap between our bodies was non existing when the movie was over. It felt nothing but good being that close to each other. She clearly shared my comment.

After we left the movie theater we went to one of the many romantic spots the city has to over. We grabbed a couple of snacks and some drinks on the way the there. Then we had a sunset picnic. While cuddling next to each other on a not to comfy bench.

While it got darker it got a little bit colder, but we staid watching the city lights go on. To keep ourselves warm we cuddled next to each other. And then it happened. Our eyes met. And we shared our first kiss. It made us both feel all warm and fuzzy inside.

But it didn’t took long and it got to cold to sit outside. At least with the revealing clothing both of us had on our bodies. So we headed back home once more. And nope, we didn’t fuck each other’s brains out. We hugged, we kissed good night and we both went into our beds.

Over the course of the following week we texted the hell out of our phones. We set up a third date for Friday. This time we went to one of the fancier restaurants in town. Luckily I was able to get a reservation.

The evening itself began like our previous dates. I picked her up at her place. Then we went to the restaurant. In theory, because this time we took a cab. While cruising through town we already cuddled next to each other. But then, all a sudden a more than just serious expression showed up on her face: “I have to tell you something.”

I signaled her that I was all hers. She made it quick. We only had a couple of minutes left inside the cab. She told me that she had sex with her roommate over the course of the last two years. She also told me that they had stopped doing it the day we had set up our first date. Then she asked me if this was a issue for me?

I took a deep breath in and out then I shook my head. I told her that it was no issue for me. Because her fucking her roommate was a thing of the past. So now worries from my side. A more than just relieved expression appeared on her face when she heard that I had no issue with her doing. Then we hugged each other, we kissed each other and then it was time to get out of the cab.

To my surprise, and out of pure luck we got some of the best seats the restaurant had to offer. The food was awesome, the mood was relaxed and two people more or less were constantly looking into each other’s eyes. While taking every opportunity to touch each other, to feel each other’s bodies.

After dinner was over, we boarded another cab to bring us back home. Again, we were sitting as close to each other as anyhow feasible. Our bodies were touching, and then our eyes met again. We shared a few gentle kisses.

Then passion took over. The gentle kisses were replaced with passionate ones. Our hands were all over each other’s bodies. We had to restrain ourselves from tearing the clothes off each other’s bodies. It really took us do prevent us from putting up a live sex show for the cab driver. But we pulled the stunt. We were able to keep our shit together. At least until we made it into my apartment.

As soon as the entry door was closed behind us we just let go. We let horny take over. It didn’t took long until our clothes were scattered all through my place. In the end we landed on my bed in my bedroom. We still were wearing our underwear when it happened.

Then my hand landed between her legs for the first time. To my surprise I felt something hard, something cold, something made out of metal. By the looks of it, she was wearing a chastity cage. Yes, it took me by surprise. And yes, it put a smile on my face.

I stopped kissing her: “Are you one of those?”

It took her a few moments to process my question: “Yes, I am. I am a Sissy. Is that a problem for you?”

I shook my head: “Nope, it just took me by surprise, that is all.”

A smile appeared on her face after she had processed the last words of mine. Then our eyes met again. Passionate kissing set in once more. It didn’t took long and our underwear was flying through the room. And to be honest, as soon as I saw the looked clitty between her legs, my dick got even harder.

A few minutes later she wrapped her lips around my rock hard dick. She knew what she was doing. Her sucking on my rock hard dick felt nothing but awesome. It didn’t took long and my moaning was filling the room.

To turn me on even further she took care of my balls. At first she squeezed them gently. Then she she squeezed them harder. While she still was sucking on my dick. I came closer and closer to an orgasm while my moaning got more and more intense.

Then she took my dick deeper and deeper. In the end I went in balls deep. I fucked her down her throat. She even asked me to grab her head and push her onto my rock hard cock. It all felt nothing but awesome. Now my eyes were running in circles. I lost it. I just let go.

My dick went in and out of her mouth. While she was squeezing the cum out of my balls. I was close. I stopped holding back. I dumped a enormous load down her throat. My balls were aching, my body was trembling while I had an orgasm. And she swallowed every last drop of my cum.

After I had pulled out my cock she looked up and smiled at me: “Thank you for filling me up. And now, time to get you hard again.”

Moments later my half hard dick was inside her mouth again. She kept on sucking, she kept on squeezing my balls, it didn’t took long and my horny was in full swing again. It didn’t took long and I wanted to stick mine inside hers.

I pulled my dick out of her mouth. I took her, I turned her around, I made her go down on all of her four, then I got some lube out of my nightstand, I drowned my dick and her asshole in it, then I went in position.

A couple of seconds later my dick slid inside her asshole. Her dirty whole wrapping itself around my rock hard dick felt nothing but good. I went in balls deep, but I took my time. I gave her some time to adjust to the sensation of my dick going up her ass.

Then I gave her one gentle, but deep thrust after the other. It didn’t took long and our moaning was filling the room. It didn’t took long and her eyes were running in circles. While my dick went in and out of her tight fuck hole.

But gentle and deep wasn’t enough for her. She asked for more. She got more. I fucked her hard and deep. But I still took my time. I enjoyed every thrust I gave her. And so did she.

Her caged dick bounced back and forth with every thrust I gave her. I began to loose it too. Both of our minds were drifting off. It didn’t took long and all that mattered for the two of us was the sensation of my dick sliding in and out of her dirty fuck hole. Fuck, it felt nothing but awesome.

One hard and deep thrust followed the previous one. I came closer and closer to an orgasm with every thrust I gave her while sweat was running down our bodies. While her hands were looking for something to hold on to. She came closer and closer to an orgasm too.

And then boom, my balls unloaded themselves again. For the second time within an hour. It came nothing but good. My legs were shaking, I collapsed onto the bed. I was gone. She came with me. Her whole body was trembling. She was gone elsewhere, she collapsed next to me.

After some time regaining ourselves, after some time catching our breaths, after me cleaning her ass off my dick, we cuddled next to each other on my bed. Her head was laying on my chest. We shared the occasional gentle kiss.

And she told me about her past. About her sissification so far. About how her roommate had helped her turning herself into a woman. I listened, I nodded with my head, I showed her that I understood her and in the end I asked her one question: “Do you want to continue on your journey?”

A enormous smile appeared on her face: “I’d love too.”

An even bigger smile appeared on my face: “I would love to be there for you, on your journey. I’d love to help you turn yourself into an even hotter woman.”

NSFW: yes

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