From Hate to Love

I've slept with my mother-in-law. Never thought that would happen.

I met my wife ten years ago in college. After dating for a few weeks she introduced me (Tom) to her parents and we hit it off. They kept saying what a great guy I was and was pleased that I was a better choice compared to the other 'losers' she dated. Her dad, Bill, was a commercial real estate consultant, while her mother, Amanda, worked on the local air force base in personnel. Her mother was extremely beautiful and feminine. They say if you want to see what your future love would look like, look at her mother. I was pleased. Amanda was 41, five feet tall, long brown hair, and had these deep blue eyes. When she talks to someone her eyes just pour into you. Most people would glance away occasionally, but not her. Amanda would keep on staring into you. She always wore dresses, heels, makeup, perfume, nails painted, etc. Even if she was just staying home that day she would be dressed up. It was great getting along with the 'parents'. I did not mind going over there all the time; especially at night when she wore her satin pajamas and gowns. I honestly never seriously considered making a pass at her back then. I knew it wouldn't go anywhere. I fantasized about her often, but never took it beyond that.

Beth and I dated for a year, and I knew she was the one for me (and not just so I can see her mother). I did inform Beth though, that I cross-dress at times and wanted her to know about my skeleton in the closet before she married me. I expected a flat out no, but Beth said she needed to think about it. I answered all her questions about it; I wasn't going to dress around her, but needed time to do it. I gave her space and didn't want to lose her. I did love her and she was the best I ever found.

Beth asked her parents what they thought about it, and they went ballistic. I was no longer a good choice for her and they wanted nothing to do with me and demanded Beth stay away from me. They claimed I was going to hell and needed 'Jesus'. They were the typical hypocritical churchies. I was going to hell because I wore women's clothing, but they swore all the time, said God damn this, they never went to church, drank, and her dad even smoked a little budda on the weekends. Screw them. Yes, Amanda was hot as hell, but I wasn't in love with her.

Beth ultimately chose to marry me, and was disowned from her family. I admired her and was honored she chose me over her family. We got married in the local courthouse and went on with our lives, without her parents; had two kids, bought a house. My wife is beautiful, but not like Amanda. Beth is completely opposite from her in regards to her femininity. Beth never wears dresses, or does her nails, or heels. Her sexiest outfit is a long flannel gown with a strip of satin on the pocket. It was up to me, and Victoria Secret ads too keep my feminine admiration at bay.

In February of 2008, Amanda ran a red light and was hit by a dump truck. She wasn't expected to live. She had several broken bones from her left shoulder, ribs, hip, and her leg. She was placed in a medical induced coma for two months. There were several times she flat lined and the doctors told us there wasn't any hope of a recovery. Miraculously she pulled through. After extensive physical therapy she was able to talk, and move around a bit. She does have permanent injuries. She has several pins holding her left hip in place and her left arm is paralyzed. She can feel her left arm and fingers, but can't move them much. The accident made her realize what was important in her life and she immediately made amends with Beth and met her grandkids for the first time. At first, Amanda and Bill were very timid around me and didn't really talk to me much. I just stayed out of their business, and they stayed out of mine. Gradually, though a truce did form between us and we started visiting them on a semi regular basis. There was always this air between us, but as long as we just talked about the weather, and work everything was fine.

In early August of 2010, I get a frantic call from Amanda that she is broke down in Columbus, and needed a ride back home. Bill was away on a meeting in Indiana, and he wouldn't answer the phone. I was tempted to make some excuse so I could just stay home and enjoy my one day off in over a month, but I did the right thing and drove the hour to pick her up and take her home. We had a real heart to heart on the way back and she apologized for pushing Beth and I away. She really regretted missing out on the first eight years of her grandkids life and vowed to make it up. She apologized to me as well. She realized that she isn't perfect herself and what I did on my own wasn't a concern to her. I agreed.

Amanda started calling me on a regular basis and I have to say that we became good friends. She cried a lot complaining about the fights her and Bill been having and how she thinks he is having an affair. She came over often as well. She was forced to go on disability retirement and had nothing else to do during the day. I did enjoy looking at her again; although she wasn't exactly like how she used to be. She lost twenty pounds and is around 105; a little too skinny for my taste. She is 51 now, and the injury has taken its toll on her. She limps real bad and needs a cane, and she does lean to the left because of her shoulder and arm. The accident didn't change her femininity though. She still wears makeup, dresses, hose, nails, etc. every day. The only thing she can't wear anymore is high heels. She still looks deep into my eyes and will not glance away at all.

On Fridays, Amanda and I started meeting for lunch at local places. Beth was okay with it, kids were in school and Bill was out of town every Friday; no one had a problem with it. I did enjoy her company, and it was a plus to be able to see what pretty outfits she was going to wear. I didn't lust after her like I used too. I just admired her femininity.

Amanda and Bill moved to a new house down the street from us in early December of 2010. I helped Bill out a lot; especially since Amanda couldn't move her arm. I did a lot of lifting, unpacking, and putting things back together again. Amanda wanted to thank me for helping out so much and offered to take me out to lunch on Friday. A real fancy restaurant that her friend was the owner/ head chef of. Suit and tie type of place to eat. I told her I couldn't dream of affording to eat at a place like that, but she insisted she would pay for it; especially since it would be for free. It's nice to be friends with the chef.

I got all suited up and head to her house to pick her up. She looked amazing. She wore a short cut red satin dress with spaghetti straps. Her hair was all done up and her makeup defiantly enhanced her beauty. She wore pure gold hoop earrings and black stockings. She asked if I thought she looked good. I didn't lie and told her she looked beautiful. She said she was pleased, especially since it took her three hours to get ready. She asked if I could help her with clasping the back of her stockings with her garters. Bill wasn't there to help her and she couldn't do it with one arm.

"I'd be honored." was all I could reply.

"Don't get any funny ideas," she teased. Amanda turned around and I lifted up her dress just far enough to get the clasp and attach it to her stocking. I did briefly consider taking my sweet time and maybe 'accidently' brush a finger on her hose or her satin panties, but I behaved myself and got it done quickly. She sat down on the couch and slid on a pair of black high heels.

"How are you going to walk in those?" I could barely walk in heels and I don't have a hip being held in place with pins.

"You are going to have to be a gentleman and hold on to me." I was okay with that. I escorted her out to the car and it was a little awkward with her weight pulling down on me, but I was not complaining. We went to the restaurant and I had the best steak I ever had in my life. I couldn't dream of spending $80 for a twelve ounce rib-eye, so I was glad someone else was footing the bill. Her friend came out and the three of us talked about nothing for a bit, and she returned to the kitchen.

At lunch she kept praising me how good I have been, a nice man and father, and about the wasted years she spent away. She started crying towards the end as she brought up Bill and her suspicions she had about his affair. He is always gone every weekend for work related meetings, and no one answers the phone numbers he leaves. She talked to one of his coworkers and he said that they don't have out of town meetings. She complained that they haven't had sex in eight months and he told her she isn't pretty since the accident. Her crying was bringing attention to us, and it did make me feel uncomfortable. She never took her eyes away from mine and it put me on the spot. I told her I thought she was beautiful and even told her I found her way more attractive than Beth, but don't let her know. She blushed.

I drove her home and helped her get inside. It was very difficult due to her stumbling around due to her heels. I helped her sit down on the couch and thanked her for lunch and I had a great time. She wanted me to sit down next to her to chat some more. I apologized, but I was meeting a friend for an Xbox Live match before I had to get the kids off the bus. She crossed her legs and gave me a pouty lip and asked again. I glanced at her crossed legs and thought, what the hell. I tossed my jacket to the side and sat down. I started thinking of a way to rub her leg just for a second. I never felt a smooth leg encased in pantyhose before. The only experience I had with pantyhose was on me, so I was dying to feel it on someone else. I was all nervous and kept glancing all around talking about minor things trying my best to come up with some plausible way to touch her without making it look like I was touching her. She kept staring at me and it was driving me nuts. I was about to stand up and leave. I couldn't take it anymore. I didn't want to make a stupid pass that would blow all that we have gained in the last year and a half. Then the phone rang. "I wonder if that is Bill." She took my hand and I helped her up while I was still sitting next to her.

Due to her heels and an awkward grip on my hand she lost her balance and fell right on top of me with her knees to my side and her face inches away from mine.

"Are you okay?" I asked trying my best not to get an erection with her sitting on top of me.

"I'm so sorry." She stares into my eyes.

"Don't be." Amanda kept sitting on my lap just looking at me as the answering machine picked up. A pre recorded telemarketer started a spiel about lowering interest rates.

"Are you hurt?" She asked.

"No." I stare back. Her breathing has increased and I could feel her breasts pressed slightly against me.

"I should probably get up."

"Take your time, I like the view." I tried to say it in a half joke, half serious manner. She continued to stare at me. I swallowed hard. There was no hope in containing my erection and I knew she had to feel it. A few pieces of fabric were all that separated my penis and her vagina. She leaned into me and placed her lips on mine with her eyes staring into mine. I was shocked at first, but returned the pressure. Our mouths opened and our tongues met. I realized that this would be a great moment to sneak my hands on her legs. I let out a moan as my hands caressed her smooth nylon covered legs. I almost had an orgasm and thought that would have been a great way to kill the mood. I followed her legs up onto her satin panties and up onto her breasts. She leaned back and I dropped my hands figuring that she was stopping. I was devastated. She just sat there looking at me as she grabbed my left hand and guided it upon her right breast and then my right hand upon her left breast. She was a C cup and with her being skinny, it made them look huge. I rubbed my fingers across her nipples that were protruding the fabric.

"Tom," She whispered to me. She kicked off her heels and stood up. I stood up as well hoping we would make it to the bedroom. She walks away from me and yes! Towards the bedroom. I follow her in and she stops facing the bed. I wrapped my arms around her and started kissing her neck. I allow my hands to rub all over her satin dress. I had never been with a woman that was dressed this way before. I begged and pleaded with Beth to wear something feminine; a satin nightie at least, but she always refused. I was getting a lifelong dream come true. I didn't feel bad about what I was doing. Yes I admit it was wrong, and Beth's lack of femininity isn't an excuse to sleep with Amanda, but I was going to experience this at least once before I died.

I reached the zipper on the side and slide her dress off. It fell into a satin puddle on the floor. Amanda turned around and our lips met. We took our time exploring each other's mouths and I loved kissing her neck with that perfume. I got Beth perfume one year for her birthday. Never used. I would enjoy every whiff because I didn't know if this would be a one-time thing or not. I picked her up and laid her on the bed. I took off my tie, shirt, undershirt, socks, and pants.

I kissed her forehead, her eye shadow covered eyelids, to her cheeks, to her painted lips. I explored all over her neck and moved on down to her breasts. Her nipples were the perfect size compared to her breasts. I hate abnormally big nipples and abnormally little nipples. I started licking and sucking on them. Her right hand caressed the side of my face and she frequently ran her fingers through my thick black hair. I went on down lower and kissed her stomach and onto her legs. I kissed, licked, and nibbled my way all over her nylon stockings. I caressed the satin on her garters while I rubbed her smooth legs. Rubbing nylon covered legs is the best physical feeling in the world for me. I died and gone to heaven. My fingers ran along the sides of her white satin panties. And eventually found their way underneath them. She wasn't super wet, but she defiantly was excited. I was pleased to notice she doesn't shave. Beth has it all smooth and I don't care for it. In order to take her panties off, I would have to undo the garters, and I wasn't going to take that away. I pushed the crotch fabric to the side and lowered my face into her vagina.

"Oh God, Bill never did this" She gasped. Truth is I never had either. Every girl I have been with, including Beth, never wanted me to go down on them. I knew better than to go straight for her clitoris, so I took my time licking the sides of the wall and working my way into her cavity. She started twitching her legs and breathing hard. I continued tasting her, and it wasn't exactly all that I hoped for. I didn't care too much for the taste, but she was enjoying it so much, that I wouldn't stop. I licked my way up to her clitoris and she lost all control of her voice. She started moaning loud and spreading her legs and closing them around my face and back out again. I started licking circles around her clit and I slid two fingers in to her vagina, finger fucking her. I kept going at it and was bound and determined to make her cum. I went on for several minutes and in time my tongue started to go numb. She kept moaning and thrashing her legs around, but she wasn't getting anywhere. To my relief she told me to lie down.

I did as I was told. She climbed over to me and I helped her slide my underwear off. She didn't gasp in joy at my five inch penis, but she didn't stop our session either. She took my underwear and wiped her juices off my mouth. She leaned down and started with my forehead, eyes, cheeks, mouth, neck, nipples, on down towards my cock. She got on her stomach and made herself comfortable. She softly grabbed my cock with her long feminine fingers. I watched in pleasure as she slid my cock into her mouth. She didn't go all hard and vigorous due to only having one hand, but Amanda knew what she was doing. I normally get the hard Hoover vacuum job from Beth. Three minutes and Beth would have me blowing.

Amanda took her time licking and softly sucking the tip to putting my whole cock into her mouth. Amanda had a lot more endurance than I had. She sucked me for over twenty minutes with her eyes staring at me the whole time. With Amanda looking at me while seeing her tongue on the tip of my cock was almost enough to tip me over. I continually had to fight from blowing all over her face. I'm not a porn star and need several hours to reload. I want the whole thing in case we never get to do this again.

Amanda finally relented and laid down on her pillow. I climbed on top of her and we started kissing again. I thought she might be put off that I now had vagina breath, but she didn't seem to mind. Her tongue danced around mine.

"Put it in." She whispered.

"Yes ma'am." I whispered back. I reached down and moved the crotch covered satin to the side again and then slowly entered her. She took a deep breath as I got all the way in and smiled at me with those deep blue eyes. I started slowly thrusting into her as she wrapped those awesome nylons around me. We started kissing again and I loved the way her erect nipples brushed against my chest. She would constantly reach up to touch my face, shoulders, arms, and even my nipples. I varied my speed from going fast to slow, to medium, to deep and shallow. I wanted to discover what technique she liked best. I spent the next half hour trying to narrow down her favorite. She liked the slow sensual movements where I would go slow and deep. We kept kissing and continually explored each other's mouths. I knew I was doing something right when she started to breathe deep and moaning as I pushed all the way into her. She started getting louder and louder while her legs got tighter and tighter around me. She closed her eyes for the first time and whispered God several times. She moaned and I felt her vagina pulsate against my cock. I wanted to keep on going and not let this end, but with all the experience with her pantyhose, her satin, her tongue, and now her vagina constricting on my cock was too much. I grunted as I shot load after load into her. She thrusted her hips up to counter my movements and after a minute I collapsed next to her. She curled into me slowly rubbing her legs against mine. I wrapped my arm around her and pulled her close to me and gave her a couple kisses on the lips and one on the forehead. She looked me in the eyes and giggled a few times.

"I haven't had an orgasm in about fifteen years." She exclaimed as she placed her right hand into my left. That made me happy. Maybe she would like to do this more often.

"Well we could try again soon and maybe it won't take fifteen years to have your next one." I was hoping for an immediate yes, but she didn't answer. We laid there for another twenty minutes just staring at each other, with the occasional kiss. I had to go and pick up the kids so I finally got the nerve to ask her if she would like to do this more often, not every Friday, but make it a regular thing. She still didn't answer. I asked for at least just one more time, and she still wouldn't give me an answer, but Amanda did give me a long kiss.

We have gone out to eat a couple times since and still chat on the phone; and visit each other, but I still can't get a clear answer if it was just a one night stand.

I hope not.