Becoming More Feminine

As I sat there looking into the mirror reminiscing of my younger years when I had a full head of hair, I now see a man with a receding hairline. My wife Amy who said she would love me no matter how I looked, started expressing that something was missing in her life.

I met Amy in college she was a gorgeous brunette with perky tits and a curvaceous body that most women were envious of. She admitted that she did had some lesbian experiences with her old college roommate Jen, because of this she was attracted to guys with softer features as she took the more dominant role in the bedroom.

Since I had long wavy/curly hair, big lips, wider hips, and at 160lbs I was just the man she could see herself with. In the bedroom she always like to be in control, always on top and would often make me go down on her, but as of lately I noticed our sex life diminished to maybe twice a month and often didn't go for that long.

One day she surprised me with some hair regrowth pills that Jen told her worked great for her husband Jason. I thanked her so much hoping that I could get some of my hair back and create some of that physical attraction that she missed.

The first week of taking these pills I didn't notice much change to my hairline, one promising effect was that I wasn't getting handfuls of hair when I showered. Another side effect was I notice my skin seemed to be very soft and any acne that I had was clearing up. Fast forward a few weeks and I started to notice that my hair was growing back and seemed to be thicker than before I started losing it, Amy sure seemed to notice because she started to become very horny and frisky.

One night she was riding my cock telling me how she was going to make me her lesbian bitch lover and that my cock belonged to her. She grabbed my tits and started twisting them, I never notice before how sensitive they were it was like a mixture of pleasure and pain.

I was on the verge of cumming when she said, "No you're not cumming in me bitch."

She got off of me and started giving me a handjob, I must admit that I was disappointed I didn't get to cum in her but she like to be in control. As she was stroking my cock she said, "You bitch, I'm going to tell all of my girlfriends that you're my boi toy."

I was surprised when she started rubbing her finger around my asshole. At first I was hesitant having her do that but then I got used to it, as she was rubbing my asshole she stopped giving me a handjob and started rubbing my tits again. She has played with my tits before but I don't remember them being so sensitive. Since I was so preoccupied with the feeling on my tits I didn't seem to notice the pressure she was putting on my ass until her finger went all the way in. I grabbed the sheets and tried to get away but she kept pushing deeper and deeper until she couldn't go any further. I told her I don't know if I like this but she told me, "Shut up slut, you belong to me."

As I laid there while she fingered my ass and played with my tits I started to notice that my dick which was soft at this point started leaking cum. I didn't know what was happening to me but the more she fingered my ass the more it felt like I was going to cum. I blacked out for a second but the next thing I knew I was cumming without even touching my dick. It was the most intense orgasm that I that ever had

I begged her to stop at this point but she kept going, next thing I knew I had another orgasm and two more in succession after that. I had no idea she was this freaky but in a strange way I absolutely loved it, Amy said she was sorry for not stopping but she got carried away in the moment. I said, "It's ok I kinda like it."

She raised an eyebrow and said, "Really?"

We finally went to bed with her crawled up next to me with me being the little spoon with her arm draped over my hips.

The next morning my tits still hurt and it looked like they were kinda swollen. As we sat at the kitchen table talking and drinking coffee she notice that I was rubbing my tits and seemed in discomfort. She asked, "What's wrong?"

I told her, "You were kinda rough with me last night, my tits hurt and are swollen."

She again apologize but said, "You'll have to get over it because we're going out to lunch today with Jen and Jason."

I told her I don't know if I'll be able to go because of how sensitive they were, she said, "Wait here I think I have a solution."

When she came back she was holding her bright pink Victoria's Secret sports bra, I said, "Who's that for."

She smiled and said, "Try it on."

I protested at first but she convince me to put it on. I must admit it definitely helped with any discomfort in my tits but the odd thing it almost looked like I had an a-cup because of how swollen they were. I decided to leave the bra on and finished getting ready. When we met Jen and Jason they commented on how nice my hair and skin looked, I thanked Jen for telling Amy about the hair regrowth pills. Jen looked at me with a dumbfounded look on her face, "Pills?"

I said, "Yeah the ones you suggested for..."

Amy interrupted and said, "What does everyone want to eat."

We all ordered and talked some more about life and what everyone was up to, the whole time I was thinking can anyone see that I'm wearing a sports bra.

As the next few weeks passed I noticed hair regrowth pills were working great, but I was getting concerned about the side effects of these pills. My tits had become permanently swollen and I found myself wearing my wife's bras because my shirts would irritate my tits which by now definitely looked like I had an a-cup maybe a b-cup, I also noticed that my hips had started to gain weight (I looked like a girl from behind), and my dick seemed to have gotten smaller.

I told Amy I was thinking of stopping them but she said, "I really like the way I look, could you please for me continue taking them."

To keep her happy I reluctantly kept taking the pills but a new problem arose with my hips the size they were, all of my pants and underwear kept sliding down because they weren't conforming to my body. Amy again came through she took a pair of her pants and held them up to me and said, "Try them on."

I slipped my legs through the holes but they got caught up on my boxers. She said, "You'll have to wear some of my panties to get them to fit, girls jeans don't have room for boxers."

She threw a teal v-string at me and said, "Put it on."

I said, "Why a v-string?"

She said, "You don't want people to see your panties lines do you?"

When I slid the v-string up my legs I felt so submissive and horning at the same time. The string separating my butt cheeks and since my dick was so small it gave the illusion of a smoother front. This must have made her horny because I had no idea what was going to happen next.

She grabbed me and threw me on to the bed separating me legs with her hips and grinding her hips into my waist. She grabbed a handful my hair and squeezed my boobs while kissing me, she seemed like a different person. She said, "Wait here, I want to try something."

She went to the closet and started rummaging around some of her boxes left over from college. When she came back out I was surprised to see her wearing an 8inch strap-on, I said, "Where did you get that?"

She said, "It was left over from her college lesbian experiences with Jen."

As she came back to me on the edge of the bed she started lifting and separate my legs she spread some lube on my ass and started stroking her cock with it. I said, "Amy I don't know about this."

She responded, "I need this slut you're going to know who wears the pants and who wears the panties in this relationship."

She then started to push her cock in my ass I think she could tell I was hesitant so she went very slow letting me get use it. I was thinking this was so painful but my small clit seemed to be enjoying it as it was leaking pre-cum. Once she got the head in and noticed that I wasn't in any discomfort she asked, "How does it feel?"

I said "Ok, kinda pleasurable."

She said, "Good."

Then with one long hard thrust went balls deep in my ass. I almost blacked out from the pain and screamed stop stop, but she kept bottoming out in my ass. I don't know what got into her but she kept going and going while I begged her to stop, eventually the pain started to subside and I got that familiar feeling of when I cummed hands free.

Eventually her cock started to feel good, so good that I grabbed her hips and helped her thrust her 8inch cock into my pussy. She responded, "I always knew you were a bitch, you like my cock in your pussy don't you?"

I didn't even have to respond my clit sprayed all over my stomach and chest, she started laughing and telling me, "You are such a dirty whore."

Then she scooped up some cum in her finger and made me swallow it. It was kinda salty but in the heat of the moment it was the hottest thing ever. She pulled her dick out of me and said, "Get ready we're going to dinner with Jen and Jason."

I sat there wondering what just happened my legs were pretty weak and my ass felt so exposed and open, I manged to compose myself and started getting ready. I put on my matching Victoria Secret teal bra and v-string, a pair of her jeans which sat extremely low on my hips, and one of the most gender neutral shirts she had which was also very low cut in the front. I was worried if I bent over people would see my bra and cleavage.

When we arrived at the restaurant we didn't see Jen and Jason yet so I went to use the bathroom just before I was about to go into the men's room a hand tapped my shoulder and said, "Excuse me miss you're about to go into the men's room."

I turned around to realize it was Jason he said, "Wow from behind I thought you were a woman."

He seemed give me a once over and stared at my chest for longer than usual, I said, "It's this dam hair regrowth pills they are doing some weird things to my body. Did they do that to you?"

Jason said, "I never took any hair regrowth pills."

I was thinking I could sworn Amy said you took these. I showed him the package and asked him just to be sure He said, "Nope never used those."

I'll have to ask Amy about this later I thought. Dinner went great Amy sat next to Jen the whole time and seemed to be flirting with her which I was ok with since I knew their history. I notice there was a few time she would whisper something into Jen's ear and she would kinda look in my direction with a surprising look.

When it was time to go Amy informed me that Jen and Jason were going to come over for a few drinks and she and Jen were going to get some alcohol, I said, "We have beer back home."

Amy said, "Well Jen and I want wine."

I said, "Ok so Jason and I should just meet you at the house?"

Amy responded yes but didn't really seem to acknowledge what I was saying more like a yes to get me to shut up. Jen looked back at me and said, "Yeah we won't be long."

She wink at me and started walking away with Amy laughing, giggling, and holding hands.

When I got back home I gave Jason a beer and we talked for a while before we both needed another beer. I went into the kitchen and was bending over to grab another beer when he said, "Nice panties."

I immediately reached my hand back and felt my lower back, I had the biggest whale tail ever and there's no mistaking that they were panties when it had "Victoria's Secret" written across the waistband. Jason asked, "Do you always wear panties?"

I said, "No, it's these dam pills I'm gaining weight in my hips and my boxers don't fit only panties will fit."

Jason said, "Do they do the same thing to your chest because you have a pretty nice pair of tits."

I didn't even realize that they were that noticeable that's when realized that Jason was checking me out and he seemed to have a boner in his pants. I said, "Jason do you have a boner?"

He kinda blushed and said, "Yes, but you have one of the nicest bodies I ever seen. I mean Jen is hot but not as curvy as you."

I said, "Thanks but it not like we're going to sleep together so get your mind somewhere else."

We kept talking wondering why the girls were taking so long, eventually summing it up to a girl thing. Talking some more Jason said, "Hey Jen told me something that you and Amy tried anal is that true?"

My face got bright red and he said, "How did it feel because I have been trying to get Jen to try anal for a long time but she doesn't want to."

I still hadn't said anything and Jason said, "What?"

Still trying to think of what to say Jason said, "Wait did she stick something up your ass?"

I was still speechless when Jason said, "Was it a dildo?"

I bursted out, "How did you know it only happened before dinner just now."

Jason said, "I didn't know thaaat, Jen told me weeks ago you guys tried. I thought you fucked Amy in the ass."

There was another long pause then Jason said, "Did you enjoy it?"

I hesitate again and I knew by the way Jason was looking at me I wouldn't be able to lie, so confessed that I liked it and I actually orgasmed without touch my dick. There was another long pause and Jason said, "So what's the difference if Amy does it with a dildo or I do it with my cock."

I just about choked on my beer "Because Amy is my wife, plus wouldn't that be cheating," I said.

"So you are open to it if you considerate cheating, Amy would never find out," Jason replied.

I sat there and thought about it for a moment, I mean I cummed so hard when Amy fucked me in the ass I wonder if the real thing is better. I said, "Seriously Amy can't find out."

As Jason and I made our way to the bedroom he put his hand on my hip and escorted me through the door. When Jason pulled his shirt off I noticed he had a very muscular body and what came next I didn't expect. He pulled down his pants to reveal a nine inch thick and very veiny cock. I though no wonder why Jen didn't want to try anal she would be walking funny for days.

Jason came over to me and started taking off my shirt to reveal my teal bra holding up my a-cup boobs, he look long and hard at them and started licking my cleavage while unbuttoning my pants sliding them down. As I stepped out of my pants he grabbed me by my hips and pick me up, my legs natural wrapped around his waist and I could feel his nine inch monster poking at my pussy.

As he laid me on the bed he asked, "Do you have any lube?"

Seeing as Amy fucked my ass two hours ago and it was still lube up I told him don't worry about it. With that he started French kissing me while I laid on my back with his cock poking at my pussy. He reached down and pull the string of my thong to the side and started pushing his cock into my pussy. Even though I got fucked two hours earlier Jason's cock still felt massive. Jason said, "Wow you're so tight am I your first?"

I nodded my head and he slowly started sliding his cock further and further into my pussy. I swear I could feel every vein as he kept going until he bottomed out. Jason said, "I never thought anal would feel this good, gosh you're tight."

He started pulling back out, just before he pulled all the way out he slid his cock back in. I though Amy's strapon felt good but there was something about Jason's cock and how it slid across my prostate that had me in ecstasy. Every time he trusted into my pussy my clitty leaked a little bit of cum and I was having mini orgasms. I kept my legs wrapped around his back helping him pound away at my pussy, when I started to feel the biggest orgasm that I obviously had not control over building in my life.

I told him, "Keep fucking me, fuck me like you fuck Jen."

I'm not sure if it was the dirty talk or my tight virgin pussy but he started breathing heavily and his thrust started to become faster and faster. Next thing I know my body started convulsing, I started screaming like a little girl, my clit started spraying everywhere, and my pussy started having contractions around Jason's cock. That sent him over the edge and he gave one more powerful thrust and started grunting, I felt his cock flexing and a warm feeling deep inside my pussy as Jason was cumming deep inside me. By the time Jason's cock stopped flexing my pussy felt so wet and sloppy, his cock slowly started to soften eventually fell out. Jason laid down beside me and start spooning me with his cock nestled between my well used but cheeks where we eventually fell asleep.

Part 2 possible depending on the responses.