My Story Pt. 02

Ultimate Cuckold Phase:

After my wife's initial cuckolding of me, our relationship seemed to grow stronger. Our sex life was better for sure. I was extremely happy she did this for me and she was very conscious to make sure I felt loved, as I think she really enjoyed the sex with Simon and wanted that to continue. As I could not give my wife an intercourse orgasm, I was happy she found someone who could. My happiness was tied to her happiness. Knowing that I was a cuckold also brought me happiness. I can't explain the feeling, but it is always there that I am a cuckold. Maria would see Simon once a week on average. If it was a weekend night, she would spend the night with him sometimes, but always returning to me in the morning to give me my reward. Simon would occasionally re-brand Maria with a hickey just to remind me he was fucking my wife.

About six months later I reminded Maria we had reached our previously agreed upon time period to start having kids. We agreed early on that we would wait five years before having kids, and we had pushed that out to seven years as Maria was doing well at work. Naturally we discussed her (our) arrangement with Simon. She asked me if she would need to stop seeing him, or if she should ask him to wear protection.

Now I mentioned earlier that I had saved my favorite cuckhold stories. What I didn't mention was that my favorite ones were either where the cuckhold sucked the lovers cock to get them ready, or cleaned them up afterwards, or the ones where the lover got the wife pregnant (actually liked these the best). I told Maria she didn't have to stop seeing Simon or ask him to wear protection. I told her it would be even more exciting if there was a chance that Simon could get her pregnant. She thought it best to tell Simon that she was going off the pill and let him decide if he was OK with the possibility of getting her pregnant. She didn't want to trap him into a child unless he wanted one.

After Maria told Simon about us wanting to start a family, so came back and told me that Simon was more than just interested in the possibility of getting her pregnant, he wanted to be the one to get her pregnant. In order for that to happen, I had to stop eating his cum out of her pussy every time, and that if Maria and I had intercourse, vs. outercourse, that he wanted me to wear a condom. I had mixed feelings about this. On one side, I loved that Simon was starting to dominate me, as I had said earlier, I am a submissive male. On the other side, I was wondering if I was letting it go too far.

So I asked Maria what she thought of this and what did she want. She assured me that she loved me, but she also wanted it to be Simon to put a baby in her, she found that extremely arousing, and knew I would also, based on my favorite loving wife stories that I had collected over the years. The way she looked at me and how happy she was, I could only agree. In for a penny, in for a pound I thought. I did tell her I had one condition, that I wanted to be there when he impregnated her. Up to this time, Maria always went to Simon's place. I never watched their couplings. Recall I am more cerebral when it comes to getting aroused, I like to read about it or imagine what is happening. But now I wanted to be in room with them and watch. I wanted to see Simon cum inside my wife and breed her.

One more conversation with Simon and we had an agreement. Simon would start coming over to our place and I could watch them make love. As it takes some time after a woman goes off the pill before she can get pregnant, Simon and Maria took several weeks off. On the night Simon came over, Maria did introductions. Simon and I had never met or spoken to each other. The only communication Simon and I had was the hickeys he had left on my wife. Where I am slightly taller and slender, Simon was a little shorter and much thicker. The term built like a brick shit house came to mind. I could see why Maria was attracted to him, Simon was a very good looking man.

There was very little small talk that evening. Simon and Maria had been apart for over three weeks and were anxious to reconnect. And I was anxious to finally see them together. We went to our bedroom in short order. I had been planning how I wanted this to play out for three weeks. I put that plan in action. Simon and Maria were facing each other, so I walked up behind Maria and I started to undress my wife for Simon. I unzipped her dress and pulled the dress down and let it fall to her feet, all the while I was giving her small kisses on her neck and her back. I then unhooked her bra and bared her breast. I then hooked my fingers into her panties and pushed them down her legs, planting some more kisses on her fine ass. Maria stepped out of her dress and panties. She stood there naked I and presented her to Simon.

My wife then began to undress Simon. I could quickly see why Maria had picked Simon to be her lover. When she removed his shirt, I could see he was very muscular and toned. When she removed Simon's pants and underwear, I really understood why she picked Simon. Simon's cock was a thing of beauty, a little longer than mine, and much thicker, as I had surmised earlier. But it wasn't the size that made it a thing of beauty, it was just the perfect proportions, the shape of his mushroom head, his veiny shaft, it was gorgeous. I immediately fell in love with his cock, as you can tell, and I wanted it. I'm sure they saw me staring at it.

Maria reached out to Simon and took his hand and led him into our bed and I went over to the chair at the foot of the bed and started undressing myself. I fully planned to pleasure myself while they made love to each other. Simon and Maria took it slow, exploring each other's bodies with their mouths and hands. It didn't take Simon long to get rock hard and I spent most of my time staring at his cock. From where I was sitting, I don't think they could tell that I was focusing in on his cock. When Maria put her mouth on his cock, I was so jealous, the butterflies were flying in my stomach with anticipation and lust for his cock.

My wife looked over at me and asked if I wanted to do the honors. I wasn't quite sure what she meant until she straddled Simon and held his cock out to me. I went to the bed and took Simon's cock and my hand. I stroked it a couple of times as my wife lifted herself over the top of his cock. I held his cock and positioned into Maria's pussy as she lowered herself onto it. She looked lovely and I leaned in and I kissed her. She then told be to watch and enjoy, and that is exactly what I did.

Now I mentioned earlier that I am a cerebral person, where I like to read porn or image in my mind what Simon and Maria were doing, but I have to say, this was a whole new level for me watching it live. My wife was really enjoying the fucking she was getting from Simon. I was being the perfect cuckold, just watching and stroking myself. I had become pretty adept at edging myself, and that is what I was doing now. I didn't want to cum too soon. I wanted to wait for them.

Although my wife started on top, Simon expertly spun them around until he was on top, keeping his cock in her the whole time. They weren't in any hurry and just slowly fucked each other as they alternately kissed each other passionately and talked dirty to one another, which drove me wild. Eventually they rolled onto their sides with my wife's legs straddling Simon. This is her favorite position to make love in but works better when having intercourse vs. outercourse. This position allowed Simon to play with Maria's breast with his hands and mouth. My wife's breasts get very firm when she is close to coming. It is like the blood rushing to a man's cock, the blood runs to her breast. Not sure if this happens with every woman, but it definitively happens to her. I could tell her breast were very firm at this point. She started talking really dirty at this point, I think to get Simon to cum with her. She told Simon all sorts of dirty things; to cum in her, to breed her, to inseminate her.

Although I wanted to hold out until they came, my wife's dirty talk pushed me over the breaking point and I had a wonderful orgasm, squirting cum all over my belly and chest. Simon and Maria weren't far behind. They sent each other over the edge and they both had a long orgasm. They remained tangled and laid with each other as they recovered. When they did untangle themselves from one another, Maria came over to give me a kiss. When she bent down to kiss me, she reached out to put her hand on my chest for balance, which landed on a pool of my cum. After she kissed me, she said she wanted to know if I enjoyed that as much as I thought I would, but she said she had her answer.

My wife then sat in my lap for a bit and we kissed each other passionately. I could feel her wetness on my groin, and it felt great. She leaned back into me, and I wrapped my arms around her. We just sat and cuddled for a bit. I told her that seeing them make love for the first time was even better than I imagined it would be. I credit some of that to the fact that Simon was trying to impregnate my wife.

Although our king bed is big enough for the three of us, I left the room that night to give them some privacy. I knew from their other encounters that Simon wasn't done for the night. I wanted to relive that memory of them together so that it would burn into my mind. To this day I relive that first memory of me seeing them together and can recall it clearly.

Simon would come over two to three times a week during the time he was trying to impregnate Maria, which lasted for several months. I was in the room every time, at least the first coupling of the night, and I would put Simon's cock into my wife every time I was in the room. I got more daring with touching Simon's cock, which always put butterflies in my stomach. I would stroke him for longer periods of time, even taking his flaccid penis and stroking it until it was hard. Since Simon seemed receptive to me touching his cock, and the two of them didn't want me cleaning up my wife afterwards and sucking Simon's cum out of my wife's pussy, I started using my mouth to clean up Simon's cock and groin area after they made love. At first, I would just lick it with my tongue, not actually put his cock in my mouth. But as I got bolder, and Simon's cock started responding, I started getting Simon hard again by putting his cock and my mouth and sucking his cock. It was my real first cock in my mouth, and it felt so much better than my dildos. I would have gladly sucked him off until he came in my mouth, but after I would get him hard my wife would shoo me away because she wanted him again.

Some nights, if I didn't cum while the two of them were going at it, I would make love to my wife with Simon still in the room. Some cuckholds see this as a way to reclaim their wife after their wife had been with their lover. I never thought of it that way, I could not "claim" Maria any more than anyone could "claim" another person. Maria wasn't mine; she wasn't Simon's; she was Maria's. The reason I liked to make love to my wife afterwards was I genuinely liked "sloppy seconds". I liked the way her pussy felt, so wet and a little loose. Knowing my cock was being bathed in another man's cum was such a turn on for me. What I didn't expect was how much of a turn on it was that I had to wear a condom in order to fuck my wife now. My hands would literally shake as I was rolling the condom on. This just proved that I was a cuckhold and showing it in front of my wife's lover was icing on the cake. You probably can't understand this unless you are a cuckhold yourself.

After the third month, Maria got the + sign on the home pregnancy test. When she told me I was so happy for all of us. I knew things had changed permanently for us, especially how Simon would Simon fit in to our lives now that his child was inside my wife's womb.

Sissy Cuckhold Phase:

The whole time that Maria was cuckholding me with Simon, I never felt any jealously towards Simon or Maria, even when Simon was attempting to impregnate my wife (I love saying those words). What I was, if anything, was jealous of my wife that she got to have Simon, especially after meeting Simon and seeing him naked in all his glory. The nights I would leave Simon and Maria to have their alone time, I would go into the bedroom next to ours and put on a sexy nighty that I had squirreled away there. I would lay in bed and when I heard them making love again, I would pretend it was me that Simon was making love to. Even if I had come earlier in the evening, it never failed to give me a mind blowing orgasm as I heard them orgasming.

As Maria's belly began to swell from the pregnancy, my attraction to her grew stronger. We had sex frequently, as her baby bump was a constant reminder that she was caring another man's child, and that had me hard all the time. Again, I think you would need to be a cuckhold to understand this. The fact that her tits were growing and getting firmer was an added bonus. When we were making love, I would look at her naked belly as I came, and it always made it special.

About six months into the pregnancy, her and Simon came to me. They wanted to talk. I was a little nervous what this could be about. Maria started by explaining that a few months before she came to me to ask if I wanted her to make my cuckhold fantasy a reality, she had found my trunk. It was totally by accident, we had matching trunks. I didn't realize she had some items in her trunk, or that the trunks used the same key. She thought she was getting into her trunk when she saw my stuff. She didn't quite understand why I had those clothes, until she started reading the stories I had saved in the trunk. Over a couple of weeks, she read all the stories I had in there. Instead of being angry with me that I hid this from her, she said it turned her on. She asked if I remembered that she was attacking me nightly during this time. I thought it was the fantasy play, but it was from her reading the articles I stored away.

She also told me the reason it took her so long to find someone, i.e. Simon, was that she was looking for someone for the two of us, not just for her. I was a little confused at first what she meant by this, but then Simon came over and gave me a kiss on the lips, not a quick peck mind you, and handed me a wrapped package. Maria told me they had gone out and bought me this gift. My hands were shaking as I opened the gift, partly from the kiss I just received, and partly from anticipating where this was going. In the box was a white silk nighty with black lace, matching panties and bra (all from Victoria Secrets), thigh high black nylons and a pair of breast forms. It was a gorgeous set and sexy as hell. Maria said she didn't know if I was still a virgin in that way, but they got white anyways. I told them I was still a virgin in that way and that I loved the outfit.

Simon then asked if he could take my virginity. I told him I would be honored if he took my virginity. My wife then asked me to come with her so she could help get me ready, and also to bring the package. Maria was serious about helping me get ready, and she was serious about doing a good job.

Stage 1 was focused on my body hair. Although I had been shaving my legs on and off for some time (I love shaving my legs, I find it extremely sexy and it makes me feel so feminine), Maria had me shave everything and every place. She left a well-trimmed small triangular patch right above my cock that matched her patch. She mentioned that Simon liked her little patch. She then had me shower and use her shampoo and soap (although I had been using them for some time, she didn't know that). After the shower, she covered my body and one of her fruity smelling lotions.

Stage 2 was applying nail polish to my toes and fingers. This is a much longer process than I thought it would be. My wife applied two coats, and we had dry time between coats of nail polish.

Stage 3 was doing my hair. Although I didn't have long enough hair back then for her to do much with, she was able to fluff and bob it to where I looked like a woman with short hair.

Stage 4 was my face. It started with my eyebrows, lots of trimming and plucking. Plucking hurts by the way, at least when you first do it, after you've done it awhile it seems to dull the pain. Then the make-up. I've done my own make-up before, but I never knew what I was doing. I tried YouTube, but never could quite master it. Knowing how hard it is, I was very impressed with her skill in this. She didn't try to teach me anything that night, telling me there would be time for that later, signaling to me this wouldn't be a one-time thing, which I was very happy about. The very last step was applying lip gloss that matched my nail polish.

Who knew it would take almost 3 hours to get ready. Maria was meticulous about everything. I never took longer than 45 mins when I was doing it for myself, but then again, I never looked this good when I did get ready, and damn I looked good. I could definitely pass as a woman. I was going to have to adjust my expectations on how much time I needed to spend to get ready from now on, as I wasn't just doing it for me any longer.

Well, I wasn't quite ready, I was still in my wife's robe. I needed to put on my outfit. I put on the panties first, as I love having panties on. I didn't bother doing any tucking, as I knew they weren't going to stay on long. I then put on the matching bra and inserted the breast forms. I had previously been stuffing my bras with various items. I always wanted breast forms, but they were hard to find and expensive. But as soon as I put these in, I regretted not buying them earlier. I loved how they felt, the firmness of them and especially the weight, they made me feel like I had real breasts. I love walking around in my panties and bras, so I then put on the thigh high nylons. I always love the feel of nylons on freshly shaved legs. Lastly, I slipped the silk nighty over my head and pulled it down over my body. I really liked how I felt and looked. I like getting in touch with my feminine side, and I was very feminine in this outfit.

Maria announced it was now time to present me to Simon, but first, do you have a name you go by when you are a woman. I told her I go by Sarah, the name I would have had had I'd been born a girl. We headed to find Simon. I had no idea what Simon was doing all this time, but I was excited to go see him, and hoping he liked what he saw. We found him in the den sipping Scotch wearing nothing but a silk smoking robe. Simon could look great wearing anything, and he looked delicious sitting there. My wife did introduction; she said Simon, I would like to introduce you to Sarah, Sarah this is Simon. Simon looked pleased at what he saw. He stood up, came over to me and took my hand and kissed it. I wrapped my arms around him and drew him into me and kissed him passionately. I opened my mouth and invite his tongue into me. I pressed my body, especially "my breast" into him to let him know I was his to take. I was finally submitting to a man, I had waited a long time for this, fantasized about it many times, and it was happening now. I was going to totally submit to Simon, and I wanted him to know that.

Maria excused herself saying she was going and staying with friends for the night, she wanted to give us the night to ourselves. I kissed her goodbye and thanked her for everything she did for this night to happen.

Simon wasted no time and picked me up and carried me to our bedroom. I wrapped my arms around his neck, feeling so safe in his arms and planted kisses on his cheek as he carried me. Simon laid me down on the bed and crawled in next to me. We spent time just making out and exploring each other's bodies. I really liked the feel of his hands on me, when fantasizing, you don't think of the small things that are really big in reality.