Special 25th Anniversary Gift From Loving Wife (Part 2) free porn video

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We made our way home from our "wedding." The next day at work Alissa got things going (Yes, already. She was excited). She spoke to the Doctor first thing in the morning and he sent a request for me to go get blood work done at the local clinic before I met with him. I met with the doctor a week later and he became my new family doctor. He made me sign a few things that I was okay with hormones etc, which I agreed to. He asked me to strip and put on the gown while he left and then came back in to examine me. He examined every inch of me, recorded every detail including my nipple size, penis and balls. He measured my arms, legs butt, thighs, everything! He asked about woman in my family and history. I have two sisters and there are a couple of cousins on my mom's side. They were all slim, or more on the petite side. He asked about them, hips, boobs, stature and a few more things. I asked why and he thought it may help determine how the hormones will react with me. Made sense to me. He was very nice and seemed very thorough. After the first appointment he gave me a prescription for 3 months of testosterone blockers. He told me that he will send a similar requisition for blood work each time and I was to come and see him once a month to review. He wanted to keep an eye on my hormone levels for three months and if the blockers did their thing. He told me about some of the risks and was not concerned about my health at all. He thought the hormones might actually help me with a few things, but he also needed to keep an eye on me closely nevertheless. I asked him about the things and he said it might help lower my risk of heart disease, keep me from balding and help keep me a little calmer. I did not see the downside. I felt good and confident with him. I continued on with our regular games with Alissa as she was counting down the days. She targeted 3 months and marked it on the calendar. Like I said, she was excited and so into it. After a month or so, I noticed the blockers were actually having an effect on me, that I liked. It seemed that I was craving sex less and when Alissa took off my cage, it was harder to get hard, but everything else seemed to feel good. I felt a little less uptight and high strung as I normally am. I was actually losing weight, also thanks to Alissa's cooking and diet, and was maybe a little more emotional. I also noticed I gained a better sense of smell. It was weird but the doctor assured me it was normal. We continued on; I found a good routine for my pills. After the third month at my appointment the doctor had me do another blood test and told me to come back in in two days and we will start a different routine. I had the test done there and booked the follow up appointment it on my way out for two days later. When I went to the appointment, he said he spoke with Alissa and have worked out a regiment for me. He gave me my first hormone shot in my butt and said I will come in weekly for it. He also doubled the dose for my blocker pills and said everything was fine. The first couple of weeks were good, I did not notice anything other than being a little more emotional. And when Alissa took me out of my cage, I was not getting hard at all. I was getting a bit hard, but noting hard enough to penetrate her. She said she was okay with this and expected it. But she wanted me to wear the strap-on she bought and fuck her with that when she wanted. I agreed, the strap on was a bit bigger than me as well, which I know she enjoyed. And it enabled me to really fuck her well from behind, something I have always been lacking the cock size for in the past. I really wanted to keep her happy, she was so loving and on top of the moon with all of this. After these three months, I noticed my hair seemed to be softer as did my skin, like Alissa said they would. Just slightly, or maybe I was imaging it, but it really did seem that way. I know that my penis was shrinking and my balls too. Alissa thought it was great so it was easier to hide and tuck. I was not sure what to think when she said that, but I was okay with it. She also started loving my hair and wanted to always brush it for me and try different ways of wearing it. She even curled it a few times when we were alone, it did make me look and feel so feminine. We would then go have sex, or Alissa always needed to cum right after she did stuff like this to me. Since we took the extensions out after our wedding trip, my hair had grown to just on top of my shoulders, so there was a lot to play with. I kept getting comments at the office and one girl there even said I had "pretty" hair. I took that to mean it may be looking a little feminine, but I just went with it. I was just wearing it straight, but now it seemed nicer and soft and more feminine. I was constantly pushing it behind my ears and I am sure it may have looked to others that I may be doing that in a feminine way. And now instead of low ponytails, Alissa wanted me to start wearing high ponytails, or higher anyway. If she saw it low, she would call me over and fix it right away. It was an exciting time as she was always wet, always. Alissa loved wearing skirts and dresses and would often come and grab my hand and make me feel her wet panties or she would stop and lift her dress or legs so I could see her wet spot on her panties. She would then tell me what she was thinking about. It was usually about me being feminine or doing something feminine that I may have not realized. I was constantly sucking her nipples and making her cum daily. I do believe she was getting what she wanted and the good end of the bargain. I'm not sure why but it was making me so happy to see her that happy. I really didn't care about stuff that I was doing, seeing her happy and not as stressed in life was a big thing for me. We continued our outings for clothes and shoes and doing things in secret. Sometimes she would ask me to do riskier things but many times would always ask me first. Once she had me go into a salon by the downtown park where we were going to picnic, to have my hair blown out and curled first. Once done, we would stop by the car and she would ask me to change for our picnic. On that occasion, she had me wear a cute little skirt and some nice flats. The skirts were always loose and casual. We had a nice picnic and she was all over me. She loved slowly rubbing my thigh and teasingly putting her hand up my skirt. On a few other occasions, when outside our regular area, she would bring earrings or other jewelry and ask me to wear them or try new pair she found for me. She was always thinking of me. We were always trying on clothes and doing the change room thing, she really loved that...and so did I. After 4 months my nipples really started to hurt, I knew they were growing. I started to get a little ball under each nipple and they were so sensitive and sticking out. She assured me it would be okay and you could barely notice. I could notice in my guy shirts and she just said not to worry and it was just me as they did not stand out to her. She thought to have me wear bralettes more, which seemed to help, but I was worried about having to wear them all of the time so no one would see my nipples. It also seemed like I had a bit of fat or jiggle in chest. Oh no, I thought..at first, then I smiled to myself, I think I liked how this was going. I actually had breasts. They may have looked like pecs, but II knew they were not. I showed Alissa when I came out of the shower one day and she was amazed feeling me, shaking my breasts and making me squirm when she touched my nipples. She said, "Oh Amy, I think I'm going to enjoy sucking on these very soon. They look so cute and delicious. It looks like you might have an A cup already." Alissa was really great and helped me hide them in my shirts etc and so the kids may not notice. We started using these thin bandages like band-aids and that seemed to help and not show through my shirts. I guess I was not going to go to the beach shirtless anymore. She ordered me a binder online so I could wear it to hide them if they grew more, she was like that. She said I would be able to make sure I didn't have any issues at work or wherever. Over the next month or so I noticed my butt getting a little fat. When I sat down it seemed like I was sitting a bit higher or on a slight cushion or something, I just noticed a slight difference. Maybe it was in my head. But depending on my pants, even the loose ones seemed a little tighter to get on, but now less baggy. I was losing weight overall, so this really stood out in my mind. I was occasionally wearing woman's jeans and pants that have always been loose on me, but now they were not so loose, but they did feel more comfortable and I liked how I filled them out more. At the same time, I noticed my guy pants and shorts did not seem to fit well anymore. Of course, my waist was a little smaller but my ass and hips seemed bigger, not huge or anything, just a little snug as if I had gained weight. I thought I had better keep an eye on this. I was telling Alissa this and she said, "We may have some decisions to make soon on your hormones. Although I LOVE your smooth ass in your panties and filling out your pants better, you may not be able to wear your guy pants anymore." I had to give this some serious thought. My next trip to the doctor he measured me all around. My waist was down, I lost some muscle mass on my arms, chest, back and legs. My hips were a little wider and my butt was bigger in the hip measurement. He examined my chest and said I definitely had breast tissue growing and my nipples were growing. He thought at my age that it might not get much more growth in these areas and with my family history he was not worried. He said I should continue on and he gave me the usual shot before I left. I told Alissa of my growth and what he said and she said to me, "You know Aaron, I really love the way you look right now. You are very androgynous looking and can really go either way. That really excites me. It's up to you, but we can maybe have you come out a bit concerning what we are doing. I understand you would be quite nervous, but you only live once and I think we are both super happy the way things are going and I want to love and grow old with you. As long as it is with you, it does not matter to me. If I had it my way, I would certainly fully support your feminine side 100% and help you every day. We can continue to ride the line, but I feel like you may want more, am I right?" I had to think. I had come a long way. I felt better, lost weight, I loved how my skin and hair felt. I was into my appearance more and more and felt more feminine every day. I said I would have to really think about that seriously. I was nervous and not sure what to expect. At this point I knew deep inside I wanted to go further, but was so worried about my kids and family overall. I realized that I should maybe accept the fact that I was transgender. I was trying so hard to hide everything, but I was enjoying what was happening to me more and more. I really didn't want to stop. I think Alissa knew this. I did not fully answer her question. We decided to go away for the weekend and Alissa wanted "Amy" for the whole weekend. I quickly agreed and we had a nice escape at a resort about 20 minutes away from our home. Friday, I got home from work and she said she packed our things and we were ready. I was surprised as I only had on my panties that I wore that day under my work clothes and she didn't want me to change. Then I knew what she was up to as she stopped at the same hotel, we stopped at on our way out to my wedding trip. She pulled up at the front door, popped the trunk and met me at the back of the car. She pulled out a small suitcase and asked me to go into the hotel to change into everything in the case. God, she always made things so exciting. I didn't let her know, but I practically ran inside the hotel pulling my suitcase. I went to the special washroom and opened it up. Inside was a dark blue flowered halter style sun dress, and beige 3" mules. She had a matching purse, makeup, my smaller forms and jewelry. The clothes were so nice, I had not seen them before. They fit perfect and felt so good on. They felt expensive. There was a gorgeous set of bra and panting, matching bikini panties that were a soft satin gray color that were so nice. The bra had some lace around the cups and it fit perfectly. I did my makeup, put on my earrings, a couple of bracelets and she also included an anklet for me. I knew this was an anklet because I was eyeing it in a store window one day while shopping, I guess she noticed. She really does think of everything. The anklet was so delicate and feminine, it was beautiful. OMG, I was so excited to be all pretty for her and get her all worked up. The sun dress was a little short and flirty, but I didn't mind. I just had to watch it from flaring up in the wind. I made myself up, fixed my hair with a clip, put all of my things in the purse she gave me and off I went. I felt so pretty, it seemed like everyone was looking at me as I walked through the hotel, I felt so special. When I got to her, she popped out of the car and had her mouth open and said, "Oh my, you look so beautiful! You look like a model. I am so glad everything fit" I said, thank you for the outfit, these clothes feel so wonderful and thank you for the anklet." She just smiled and said, "You are more than welcome Amy! It was worth every penny for you. Here," as she tossed me the keys, "you need to drive as I am so bloody wet; I have to enjoy myself; you look amazing." I had never driven with heels, but always wanted to. When I sat in the car my dress rode up a bit and she noticed and smiled. She asked me to leave it as she wanted to look. She sat in the seat and I started too drive, Alissa pulled out a dildo from her purse and showed me. She then pulled down her panties and got that dildo in her pussy pretty quickly. It was so erotic. She started saying things to me like "You look so beautiful, your makeup is prefect. I love your silky legs as she used the dildo aggressively and was moaning while looking at me. She said, "Look, being a girl is wonderful, isn't it? I can just slip this up my dress and have some fun." She came moments later and couldn't take her hands off of me. She said she loved my skin and how soft I was and played with my hair while I was driving. The first thing we did after we checked in was go to the spa. Alissa booked us a mani and pedi. I went as I was and think I was totally passable. The girls at the salon were very nice and I got a nice color that matched the lipstick I was wearing, red. We went for dinner right after and played a bit in the casino that was part of the resort. We played a bit and had a few drinks in the casino bar. Two guys came up to us once in the bar and she held them off. The guys scattered but she did say to me, "Did you see that one guy? He was pretty cute and he looked pretty big. I bet you would like one of those in your mouth again." I just jokingly tapped he and said, "Oh stop." She then said, "Well, that is not a no, is it? Maybe our masseuse tomorrow will need a tip." She just smiled seductively at me and I said to her, "Well, do you think I should wear this lipstick then tomorrow?" We just laughed as we were both a bit tipsy. We headed to the room. On the elevator she was hugging me and just said, I looked so beautiful today and she loved me so much. We were a little drunk and very tired. As we were getting undressed in the room, she told me to put on a new nighty and panties she got me. It was white silk and felt so nice on. When the fabric went across my nipples, I guess they stuck out a bit more and made me tingle like I have never felt before. She was amazed. "Oh my god Amy, your nipples look so good in that. Come over here." Next thing I know she was feeling my nipples and it felt so good. I don't know why, they just felt awesome, sensitive, but awesome. She asked to suck them, so I lowered my nighty and she laid me down and started sucking and touching them, I then did the same to her. She got on top of me and rubbed our wet nipples and we both came a few minutes later at the same time. It was wonderful. We were tired and went to sleep right after. The next morning, we got up and showered and she opened her suitcase with a surprise for me. It appeared she bought me all new clothes for the weekend. She was so excited. Alissa was a fashionista and sometimes I was like her model or experiment, which I liked. I totally trusted her choices and sizes she had for me. She said she had the perfect outfit for my red mani and pedi. She pulled out a matching set of light pink silk panties and matching bra. The looked so beautiful and expensive. The she pulled out a gorgeous day dress. It was mostly white, like a sundress but more of an A line style with red piping and matching waist belt accent. The dress had cap short sleeves and came just above the knee. It was gorgeous. She then pulled out 4" white wedges with a beige platform. She said, "These will let your toes pop." I could not wait to get dressed, I grabbed everything and ran into the closet area, secured the items and jumped into the shower. I was so excited as I was showing and could not wait to get dressed. I go out of the shower and started. I did not need a corset on the trip as my waist was holding at 24". I started with the panties and bra, they were so delicate and silky, they felt wonderful. Then my small falsies plus everything else. The dress was perfect and Alissa zipped me up. I put the shoes on and was standing there in front of Alissa, she was just all smiles and said, "I was worried the dress might not fit, but it's perfect! Look how gorgeous your hands and feet are with your red nails. I think you may be attracting a few more men today. I asked if she could see my bra and panties through the dress, she just said, "I can see them slightly as the light is strong here in our room. I think this is perfect, if you catch the right light, you can maybe see a brief outline, nothing major, this will drive the guys crazy. You will get and get lots of attention. I hope I can catch a glimpse myself," she said with a coy smile. I just smiled and she told me to do my makeup as she got dressed. She came out wearing a beautiful sun dress with cute 2" sandals. She looked so beautiful and took my breath away. I was so happy and glad to be with her. She asked me to do her makeup, which I gladly did with a nice light day look, she was stunning. We grabbed our purses and headed down for an early lunch. We ventured out of the hotel and did some shopping and sightseeing like two girls out for the weekend. We were calling out guys to each other and woman and sharing our thoughts. Things like "I wish I could suck that, or wish I could wear that. Or, she should have worn something differently or different shoes, makeup etc. We were having fun people watching. We had a drink on a patio and had a nice chat. She brought up the massage we had at 4:00. She asked me to see if we can what we did with Andre in Vegas. I did not object and just said, "Let's see how it goes. It has been a long time for me." She said sensing some urgency, "I did not realize you missed it, do you think you need to have a cock in your mouth more often?" OMG, she was being blunt, and serious. She waited for my answer. I was nervous and not sure what she wanted to hear, but I did want more. I finally said to her "Alissa, I love our marriage, I love what we have together and what we do. I have been so happy and it seems to keep just getting better. There are two things I have to say here. The first is that what I did with Andre was awesome. It was such a great feeling I had when I made him hard and made him cum. It made me feel like I have never felt before. I was powerful yet submissive. I really liked the experience and believe it or not, his cum tasted so nice and warm. It was like a top shelf desert. It was warm, erotic and very tasty. I have thought about it many times since then. Secondly, when I did that, I saw you making yourself cum watching me and seeing your face and how much you enjoyed it, I think seeing you made me cum at the same time that Andre came. Or, maybe it was both but that was an experience I would love to repeat. And to add to that, since I have been taking hormones, I have been craving eating cum often. I'm embarrassed to say, but just telling you the truth." Alissa said, "Thank you for telling me that. I have a confession to make to you. When I saw Andre cum in your mouth it was a very proud moment for me. I LOVED watching it, you had all of your bridal makeup done and your nails and you looked so feminine and in control of that blowjob like a pro. I have never been more excited than watching you do that. And being the way I am, not a day has gone by since where I have not thought about that and gotten excited each time. I think I loved it more than you. It seems like we have some common ground here." We had a quick moment of silence and I realized we were so meant for each other. She said, "I was thinking that sucking off the masseuse was a bit of a game thing to do, but I think we need to get you cock more often. Looking the way, you do now, I do not think that will be hard to do. But I also need to watch the action when it happens, deal?" And she held out her hand to shake. I said, "Deal." "And let me be clear, I am not interested in men for any other reason." Alissa just said, "Well I hope not, but maybe you can get swept off your feet. You are so soft and pretty now and will be attracting the men." I responded, "I need you to be my wing girl and keep focused with me." "Deal," she said. "You know I do not like to suck cock Amy, but have a look around and tell me who in this restaurant would you like to suck?" she asked. Without looking, I said, "Our waiter." She just smiled and said, "I knew you would say that. You obviously noticed his big bulge. Good girl, you are coming along." We had a good laugh and finished our drinks. We finished up and continued walking around, completely in love. We had a bit to wait for our massage and this is how we spent our time. I felt so feminine and beautiful walking around. The male gaze was so strong, I do say I felt like a million bucks. For the massage, I was thinking who will it be? It turned out that the place was not really able to allow us any privacy and the masseurs were, well, they were not like Andre. But I did have fun showing a bit of my gorgeous panties to him as he took a feel. I just thought to myself, oh no, I'm really enjoying being feminine. Unfortunately, there was no cock for me at the spa and Alissa seemed very disappointed. I was not sure if that was for me or for her. After our massage, we went for a nice dinner all relaxed. After a few pre-dinner drinks we were pretty giddy. After dinner we moved to the bar area. Within about 15 minutes guys were hitting on us. Alissa did a good job of turning them away, until one guy caught her attention. He was hitting on us and alone. We were flirting and being all sexy for him. He excused himself to use the washroom and Alissa said to me, "This is the one." She said, "When he comes back, go to the bathroom and fix your makeup and get a nice glossy coat of my red lipstick on." I agreed. She said, "Leave it up to me, I will work on him and ask him." I was nervous but went to the bathroom and freshened up my makeup and had a pee. I came back and the guy was totally focused on me now. I was not sure what Alissa said but he was leaning into me pretty good. I decided within our small talk to reach down secretly to the bar, and feel his cock in his pants. It was so thrilling. He immediately perked up when I touched it. He leaned in a bit to me and started some dirty talk. I whispered to him how much I wanted to suck his cock and he just said, "I know." He was growing so hard as a rubbed him through his pants, I guess Alissa just said "her friend" wanted to suck him. We politely closed our bill and made our way to the room. As soon as I went in, I grabbed a hair tie from the bathroom counter and put my hair up as I walked to the bed, I went and sat on the edge of the bed and motioned for him to stand in front of me. He came over, I unzipped him, lowered his pants and out popped a delicious large cock. I glanced and grinned at Alissa who took a seat in view and I started to lick and rub him until he was rock hard. He was delicious and all I could think about was having his cum in my mouth. He smelt like heaven and I was pretty excited myself. Alissa had her dress up and panties to her ankles and was full on playing with herself. After about 5-6 minutes he pulled me off and I knew he was going to cum. I positioned my mouth to take it all. It was amazing, he had so much cum it tasted better than Andre and was so sweet. He first shot in my mouth and it almost choked me. I went back on him and must have had about 4 swallows before he finished. It felt like so much cum, I felt to be a very lucky girl in the moment to get that much cum at once. I sucked him dry and swallowed every drop. He then asked me if I could do that again. OMG, I said YES and continued to lick and suck him some more. At this point I already came in my panties and they were soaked, but he was so good. Alissa just looked at me with amazement and kept playing with herself. He came again in about 10 minutes and I made sure not to miss a drop. It was awesome. I made sure he was not wet anywhere or missed any cum. He backed off, pulled up his underwear and pants. I thanked him and he just left. Alissa came over and hugged me and said that was the best she had ever seen. She said, "Are your panties all wet Amy?" I said, "Oh yes, they are full of cum." She grinned and said I knew you were coming when he first shot his load into your mouth, I could tell. I think you like that part the best." She was all over me kissing me and seemed very horny. She said, "Actually, you smell like cum and it's turning me on. Please go get the strap on from my bag and fuck me now." I quickly did that and fucked her as she played with my nipples through my dress. She came so hard. We were spent after that. We changed into our lounging clothes (mine outfit was red satin short and top set pajama set) and finished off with a nightcap from the minibar. She was spooning me as we were falling asleep and I loved feeling her hands on my waist from behind and feeling my mid-section, I felt so warm and content. We fell asleep like that; it was so nice. That was our weekend. We knew our son would not be home so made sure I had another outfit for the drive. She had me wear a loose royal blue summer dress with white and red accents in it with the white wedge heels. She gave me new matching bra and bikini panties in a similar blue as well. She had a white and beige purse for me and a bracelet. I put my hair up to get it off my face and to show off my diamond earrings and off we went. I felt really pretty and Alissa had a really cute romper and similar heels on. She looked stunning again, but I felt really pretty and figured we would attract a lot of attention. She was staring at me the whole drive. We stopped for burgers on the way and everyone was looking at us, I felt so good!! I noticed I was getting so used to the heels as well. Even sitting in the car my legs were differently positioned because of the heels and it felt pretty cool to drive with heels and a dress. It was actually amazing. I was so conscious of it and it made me feel so feminine. I did like the effect of the heels on my feet and told Alissa this. She just said, "Yes, it's wonderful, you should try and wear more shoes with heels or at least some kind of rise in them. We will work on that. You are doing a great job of walking in them and moving your hips and strutting your stuff. It looks like you have been wearing them all your life." That was a big compliment, I thanked her. That was the big event on the way home. We made it home safe and I stayed in my cute dress until 9:00 as our son came home. We spent some time with him. I had to work hard to get the makeup and nail polish off and always am afraid there would be visible remnants of nail polish or makeup on. Alissa does give me a quick check before seeing our son...which this time I forgot to take my earrings out. I'm glad she caught that, although I am sure anyone can notice my two holes in each ear. One thing I did notice that night was that guy's clothes were just so boring and for me, a little uncomfortable. I just kept this to myself for the time being. As we got into about 5 or 6 months of hormones my nipples grew more. They started out about the size of a nickel and small and now the areola was close to the size of a quarter and the actual nipple was bigger. It seemed to suppress and hide better, my doctor said it was mainly because of my breast growth and they were coming along nicely. I think I was a A cup now as Alissa said, maybe on my way to a B. The nipples were still pretty sensitive, which I mentioned to him and he politely said, "I think you may want to get used to it as this is what woman face every day." He was so right, what was I thinking? My breasts had grown a little more and I loved the jiggle I felt when going up stairs and quick movements. It was also then that I noticed when I had a bra on, I was not so sensitive in my nipples, but without a bra OMG they made me almost jump when rubbing on my bare shirt or clothes. I actually was excited and thought this was awesome, but trying to figure out how to do this in guy mode and it scared me. I asked the doctor to maybe give me less of the estrogen but he said we had a good balance for my body type and lifestyle and we had to manage my hormone levels overall from a health perspective. He said he found the right blend for me as hormones were important for everyday body functions and my levels were perfect. I asked about scaling it the other way with testosterone and he said that it may have more of a negative impact on my system because of my prior blood pressure and heart health. He suggested we continue for a few months and keep an eye on it. He said he was pretty sure I would not see much more breast development at my age. He thought I may see a bit more shifting of fat to my hips and ass, but otherwise I was in great health. I guess I was thinking that this was a bit of a switch that I could turn off and on and it doesn't work that way. I told him how happy I was and I was a calmer person, but sensitive and really easy going. He said that is some of the normal affects you can experience using estrogen in your situation. It seems the testosterone was actually making you agitated and more aggressive, maybe in a way you didn't like. But this is normal for males and when their hormones go, around your age, we need to supplement to bring them in line. In your case you can say we actually supplemented with estrogen instead and found the perfect balance that way. But at least you can have a better heart, and the other things you wanted like soft skin, less muscle mass and better tempered. I think you like the way your eye color has lightened up as well. This I noticed and thought I was crazy but he confirmed that can sometimes happen to men taking estrogen. Overall, he asked, "You seem happy, you are in great health, seems like you have a great relationship and lifestyle, what more could you want?" I hesitated to answer, he was right. He said, "Let's continue on this path, let me keep you healthy and we can keep an eye on things." I agreed and he turned me around for my estrogen shot. I smiled, said thank you and left his office. Alissa always liked to be creative and loved fashion and clothes. I was getting to appreciate the differences in good clothes vs cheap stuff and how to put things together. She was teaching me well. We got on a bit of a health kick, she was cooking so well and keeping our weight down and making sure we ate healthy. Alissa had me on a routine for working out a few times a week at home but she decided we should take it more outdoors and experience somethings we have never done before. Since we could not get to do any scuba diving without going away, she thought to take advantage of our community offerings. We started doing more activities outside, hikes, bike rides, tennis and a bit of jogging to keep us fit. Little did I realize that all of these activities will require me to wear a sports bra of some sort because of my nipples. I would not be able to handle the shaking and nipple action on my own. This was a new thing for Alissa, she was so excited to help me take on new challenges for my feminine side. She ended up going shopping for sports bras for me. She would text me pictures from stores to see if I liked them and asking me about materials and more. I then had to try them all on and try them out in our room and finally settled on a couple of brands. Of course, I wearing guy t-shirts and shirts but they were a little loose on me these days with the muscle and weight loss, so you couldn't see the bras all too clearly. But if I was leaned over peddling on my bike or in exercise, there was no mistaking I was wearing one. I had to watch it when I sweated, if I had gray or pastel-like colors on, I would sweat more in the bra area and it would show through my shirt in that pattern. She also bought me woman's workout and running shorts that seemed gender neutral at first glance, which I didn't mind wearing. With my hairless legs though, it was tough not to think they were man's legs. As much as I tried to hide and conceal things, I did like the look of my body and skin. It was one thing to laser off the hair on my legs, but now my skin seemed to glow differently and look more colored and healthier, and sexy. I have to say, it was amazing. When we played tennis, Alissa teased me saying that we will go away for a tennis weekend somewhere as she wanted to play with Amy and will buy me some cute tennis outfits. She loved tennis and was very good it at, so I knew that was going to come one day. When we were really alone, say on a hike up in the hills, she would always have me put on some mascara and lipstick in the car for our hike. Any opportunity we had alone, Amy would make sure my feminine side was showing, If I left the house with a guy's shirt, she might give me a woman's shirt and short to change into. I loved that, and they seemed to fit and feel better on rather than my guy shirts. We always stored makeup remover pads and solution in the car to fix things up before we made it home. Overall, we had fun with sports and she was always anxious to suck my newfound nipples. We were really getting into shape and I could feel and see myself in a more feminine form. When I took my clothes off and was naked, I really noticed. With my waist slimmer it made my hips look wider, but when I stood sideways and looked in the mirror, my butt was sticking out a bit like I had never seen. It was pretty exciting for me, but I was also nervous. One day out of the shower and looking in the mirror I thought, what if my ass keeps growing? How do I explain this? I quickly ran to try on some of my work men's pants. OMG, they were snug and the waist was loose. I guess I did not realize how quick this snuck up on me. I told Alissa to come and check and she was helping me through it. She did turn the tables and had me put on some of my woman's pants and I could not believe how good they looked. She said, "Amy, it looks like you do have the best of both worlds right now. Can you imagine how you will look in your dresses in a few months?" I just said to her, "What am I supposed to do now? how am I going to hide this?" She said, "Oh, don't worry, no one will notice, it's been so gradual anyway. People might thing you gained a bit of weight, that's all. when you show off your small waist, that is when your curviness shows. You just need to avoid doing that for now. It will be fine. Since we are here showing off, please go put on your bikini, I want to see how that looks on you now." Oh my, what was I to do? I actually LOVED wearing a bikini and she knew it. I did that, she squealed and clapped when I came out. Alissa then asked me to lay on the bed and she went in the closet and washroom. When she came out, she had on a similar bikini. OMG she was beautiful! She quickly jumped on me on the bed, I said, "You are all wet." She responded with, "I soaked my bikini in water so my nipples will be all wet, here feel them on yours," as she lowered herself on me and rubber her nipples on mine. Wow, they felt wonderful, she saw by my expression that I liked it. She rubbed her pussy on my cock as she did this and was cumming in minutes. She turned to me after and asked if I would like to cum. I said, "Of course." She said, "Okay, don't move, I am going to fuck you." Off she went and came back with the strap -on. She told me to get up and stand on the floor and lay on the bed. She pulled my bikini bottoms down and off, lubed up and in she went. She reached around my front and started to touch and pinch my nipples in my now damp bikini top. She then started talking to me, "Amy, imagine we are on the beach in Mexico, no one around and I want to fuck you out in the open and make my special lady cum on the beach. Imagine your wet bikini bottoms and your nipples rubbing on the towel and sand and almost coming off. I'll be pulling your hair and head back making you feel so good" then I came, she stopped and said, "Good girl, we must fuck on the beach one day, it's always been a dream of mine. My dream was that I was being fucked, but I think I have a better one now to be fucking you instead. I am getting into this and I like to make you cum this way. I had no idea you loved it so much." I just turned to her and said, "Thank you, that was amazing." She said, "I think I will book something soon for us to get away. This time we may get you some full-on cute bikini tan lines." We have been off and on more with my cock cage, but she put it on this time and said, "think about how that vacation will go. I was originally thinking of repeating our wedding in Vegas, but I know you need some time to have your gown altered. Maybe we do that next year or later and this year we do a resort and beach vacation so we can do some scuba diving as well. It's been too long since we went scuba diving. I'm going to book something this week and surprise you with the place." Then she cutely said, "I have never seen you scuba dive in a bikini. Maybe we can show off your curves now in a nice wet- suit. Do you think you can handle being my full-time girlfriend trip date?" I just smiled and said, "Of course I can, girlfriend."

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My wife is the type that could be called almost prudish in her sexual desires. I've tried to get her to loosen up, but it's been a long and tough process. She believed that sex was just a little foreplay and then intercourse. And no matter how much I tried to get her to loosen up, she always resisted.We had been married 10 years before I finally convinced her to give me the occasional blowjob. She thought it was disgusting, but finally relented when I convinced her how much I really wanted it....

2 years ago
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Johnnys Anniversary Gift final

Finally five o’clock came and he was off. John grabbed his bag and almost ran to the school parking lot. Often he enjoyed visiting with his fellow teachers in the halls on his way out. No students, noise, or interruptions. Mostly because 95% of his coworkers were women, so he loved chatting with them and taking quick glances at their cute feet. He got to his truck and turned the key. Thankfully the 23-year-old bucket of bolts started up and he drove home. As he pulled up into the driveway he...

3 years ago
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How my hot wife celebrated our anniversary with a black gangbang

My wife Lola and I were having a night out at a nice restaurant for our anniversary. The conversation came around to how our lives had lost some of its spontaneity and what we could do about it. She was looking very hot in a tight dress that showcased her beautiful tits and shapely ass. I brought out a box and gave it to her. When she opened it, there was a string of perfectly matched pearls. She looked stunned, and I helped her put them on and we kissed. The conversation then continued as to...

2 years ago
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On their first wedding anniversary a jealous man watches his wife kiss her brother who was away when they were married

Normally, I’m a very jealous man, so the events of the last couple of months leave me puzzled. Excited and angry, but also puzzled. I’ve lost girlfriends because of my jealousy. I had it under enough control to ask Wendy to marry me, even though I knew she’d had a previous lover. She told me before the first time we made love several weeks before I asked her to marry me. She wouldn’t tell me anything about him, just that she could never marry him and that it was over. My...

4 years ago
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My wifes anniversary present

My name is Mark, and I’ve been married to my wife, Anna, for five years now. I’m thirty, and she is twenty-eight. We are a happy couple, because we rarely fight, and have a solid relationship. Neither one of us have ever cheated, and our sixth wedding anniversary was coming up. I was unsure what I could get her, mostly because it was going to be really difficult, to beat the gift I got her last year. I got her a heart pendant, and it cost five-hundred bucks. She loved it, and still wears it...

3 years ago
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Fifth Anniversary

The morning did not start well.

Kevin and Susan Greyson rose on a working day. It was a sunny morning and Kevin felt great. So far so good. How had it managed to go so steeply downhill from there? Well, he would later have to admit that he had nothing and nobody else to blame but himself – and her of course! He always accepted that he had a stubborn streak, and when it bit, he could not help but dig his heels in. 
He was eating his muesli and drinking his coffee, and Susan was doing the...

4 years ago
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Fucking my friends wife on their anniversary

So, like most Saturday nights this summer, Anna came by my place tonight. But tonight was different in a most awesome way. She came over on her anniversary.As soon as I let her in, Anna left no doubt about her intentions. Without saying a word, she pressed her body up against me and kissed me on the mouth hard. I kissed her back, pushing her up against my door as my free hand wandered up the front of her shirt. She was braless and I took full advantage, savoring the soft feel of her tits in my...

2 years ago
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Anniversary Surprise Chapter 1 Celebrating Their Tenth Anniversary in Vegas

My wife, Pamela Smithe, and I, Daniel Smithe, had always been fairly open about our sexual fantasies. But I thought she was holding back on me a bit. There was nothing I could specifically point to, just a feeling I had whenever I watched her when we discussed our fantasies.Our tenth anniversary was coming up, and one night as we were laying in bed after making love, Pam asked, “Do you trust me to plan something special for us to celebrate our tenth anniversary? I really want to surprise...

Bisexual
3 years ago
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Mary Deannas Anniversary Fuck part 1

PrologueLike many husbands I have had a long time fantasy of watching my lovely wife, Mary Deanna, being fucked by a Black man. For about as long as I can remember I had dreamed of her sucking and fucking a big Black Cock while I watched her and maybe even photographed or videotaped her with her Black lover. I never expected her to actually ever let any man fuck her other than myself, but one has his dreams. In fact, I had only rarely broached the subject of sex with another man with her, as...

3 years ago
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My wifes anniversary present

My name is Mark, and I've been married to my wife, Anna, for five years now. I'm thirty, and she is twenty-eight. We are a happy couple, because we rarely fight, and have a solid relationship. Neither one of us have ever cheated, and our sixth wedding anniversary was coming up. I was unsure what I could get her, mostly because it was going to be really difficult, to beat the gift I got her last year. I got her a heart pendant, and it cost five-hundred bucks. She loved it, and still wears it...

Wife Lovers
3 years ago
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Tina and Miss Cindys Anniversary Celebration

It was coming up to the very special anniversary for Tina and Miss Cindy. It was now a year since they first met and, since then, the relationship has been one in which the now nineteen-year-old Miss Cindy controlled the now sixty-year-old Tina. Tina never minded being under the disciplinary control a woman so young compared to herself and, in fact, found the need to submit to someone just a third of her own age as something of a turn on.Tina happily carried out all the menial tasks that Miss...

Spanking
4 years ago
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The Anniversary

Nicole stared out the window, her smiling reflection staring back. The Sun had just gone behind the buildings, but had not yet set. That wouldn't be for another hour. The anticipation for the evening had been growing in her for almost a week, when she found out that the bistro would be hosting a very private party, and that she had been specifically requested to serve the party. The guests would be arriving soon.The table that had been requested was a small two-top near the centre of the small...

4 years ago
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A Strange 25th Ch 01

AUTHOR’S NOTE: ‘This is my first submission on Literotica. This will hopefully be the first of many more to come. This is the first chapter in a series and I’m hoping that after reading you will love to see what happens in the next chapter. Please rate and comment and tell me what you think.’ * The story begins with Amber Kane. She’s recently celebrated her 25th birthday though now as she sits on her hotel bed, she can’t quite remember that night. She was always a little chubby growing up...

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