In Memorium...Aunt Jane

This story fits in the 'Loving Wives', 'Cross-dressing', 'Interracial Love', 'Erotic Couplings', 'Gay Male', 'Mature', and 'Romance' Categories and possibly others as well.

My name is John Murphy and the most influential person in my whole life was my aunt Jane. Actually she was not related to me. She was my mother's best friend. My father was a Naval Officer; he was a Naval Academy graduate. His best friend and roommate from the Academy was Charles Black. Charlie's wife was Aunt Jane. She and my mother were very, very, good friends. Aunt Jane was born and raised on her family estate and working farm just outside of Annapolis, Maryland. Her Grandfather had founded what was now the largest privately owned Bank in the Maryland.

Whenever possible our families got together. One of the best times I can remember was when Charlie and my father were both assigned to the Post-Graduate School at the Academy in the late 1930's. We lived on the Estate in the huge old mansion. It was wonderful. Aunt Jane had inherited the estate and farm and had the house renovated and modernized. There were several apartments and suites in the huge house.

My mother was a coalminer's daughter from West Virginia and Dad was from a poor family in Virginia, they had never lived as luxuriously as we did on the farm. Mom was about 6 or 8 years older than Aunt Jane but they loved each other and got along famously. They were as close as any sisters could be. They were both beautiful women. Mom was taller at 5' 6", while Aunt Jane was a tiny 5 footer. They were both fashion conscious and dressed very well.

I was Aunt Jane's favorite, she adored me. She was unable to have children and lavished her attentions on me. The families lived together for two years until the men were reassigned. We moved to California and then to Washington, D.C.. Washington was only a few miles from Annapolis so we spent a lot of time there when we could. We all had rooms at Aunt Jane's house.

Dad's next assignment was to Bremerton, Washington. Then we went to Long Beach., California, then to Boston, Mass and then back to Vallejo, California. When WWII started we were in Washington, D.C. again. Dad was soon ordered to sea as captain of a Destroyer, and Aunt Jane insisted Mom, my brother, sister, and I stay with her while he was gone. Charlie Black was at sea too and we felt right at home.

Mom followed the ship from place to place. Mom would receive a message that Dad was going to be in port for a week in Boston, Portland, Maine or Baltimore and she would grab my sister and be gone. My brother was in the Naval Academy, and I stayed with Aunt Jane. This was during the battle for the North Atlantic and Dad was now commanding a division of three destroyers. He sunk a German sub while escorting merchant Convoys across the ocean to Europe. When D-Day arrived he commanded a Squadron of 12 destroyers.

As the war wound down I was placed in a Military School in Laurel, Maryland. I spent some weekends and all vacations with Aunt Jane. The summer of my 18th year was spent with Aunt Jane. She was lonely because her husband, Charlie, had been killed in the war.

One evening Aunt Jane asked me to sleep in bed with her because she was lonesome. Now, I had slept in Aunt Jane's bed many times as a child but I was now a horny teen ager. My hormones were churning full blast.

Aunt Jane wore a lovely nightgown to bed and I couldn't hide my erection in my pajamas. She smiled at me, "My goodness, do I cause that? Let me see it. "WOW! Look at you, you are really a man now." She pulled me into her arms and held me tight. I didn't know what to do, it felt so darned good in her arms, her perfume was intoxicating, but I knew the slippery stuff was leaking from my cock. I didn't want to make a mess in her bed so I told her about it. She had to look again, her little hand grasped my cock and stroked it gently. She looked up and smiled, "Will you let me take care of that for you, Honey." I gulped and nodded, then watched as she lowered her mouth over my penis. Her soft, lip-stick coated lips kissed the head of my cock and then slipped over the tip to engulf the whole top half. Her bright green eyes were locked on mine while she sucked as she lifted and dropped her head again and again, while her tongue swirled around.

It was only a few seconds before I felt my cock explode, pumping Aunt Jane's mouth full of my white gooey stuff.

She held my face gently and pressed her lips to mine, her lips opened and she pushed some goo into my mouth. Jane pulled back, a small smile crinkled the corners of her mouth. "I love you my sweet baby boy. We are now lovers and I have much to teach you so that we can please each other. I love you above all others, and even though you are young, you are forever my man. You are not yet fully developed physically but that doesn't matter. If you find me with another man or woman, you need only to beckon to me with your finger and I will always leave them for you, no matter who they are. You are my god given mate forever. I love you."

I stammered something back, pledging my undying love for her. We cuddled together on her big bed, she took my hand and moved it over her body to rest on her breast. "These are my breasts and nipples. They are called a number of names, breasts, boobs, knockers and other names. They are sensitive and I love for you to caress and play with them. My nipples are very sensitive and I love to have them sucked on. Go ahead and nurse at one, you will love the way they feel. Mmmm, Yes Dear, that is very good. That is great when you suck and lick one and play with the other with your hand. You are making me wet."

I looked up, "Wet?"

"Yes Dear, wet with my body's natural lubricants it produces when I am sexually aroused. Oh! Honey you are a fast learner. Move your hand down here and feel how wet I am. This area is called my 'pussy', it is the new home for your cock. Move down between my legs. Good. I have a grip on your beautiful cock and you just move to follow where I lead you.

"Now, see how I open my legs to show you the hole inside. I want you to move closer and put the head of your cock into my hole. Ummmungh! You loved the way that feels don't you. Yes Dear, move your cock in and out to see what feels best to you. Ahhhah! Yesss, my sweet love, you are a fast learner. Change how fast you go. Oh! I think you are just fucking me as fast and hard as you can. Fuck me! Fuck me hard. Yes, just like that! Oh God, you feel better than I had dared dream. Ahhh, yesss, I feel you cumming inside me, I love to feel that. Hold me tight and don't move."

She gently kissed my lips, her tongue slipping inside to softly explore my mouth. She kissed my eyes and whispered little things about how much she loved and worshiped me. It was very erotic and heady stuff for an 18 year old, head over heels in love with a beautiful mature woman. I was totally in her spell and it was exactly where I wanted to be. At this time my adolescent growth spurt had not yet happened and I was about 5" 6" and weighed 110 pounds. I was slim and trim from running and swimming.

Aunt Jane had me stand in front of her in all my glory, she smiled, "Perfect, you are just perfect for some games I love to play. Your beard is very light. Your face hasn't lost its smoothness. You are quite lovely. Now turn around for me. Oh! Dear! Your cock just drives me crazy, you are fully grown there, come let me show you some other ways to enjoy each other." She told me to crawl down between her legs so she could teach me about pussies.

She spread her legs and gave me a lesson on the names of all the parts, she made me touch and lick each part. My cock was fully erect and she giggled, "I know what he wants, but until you lick me out good and get me really hot you are not going to get it." I tried to remember everything she taught me and buried my face in her pussy. I sucked in the thin delicate lips and played with them in my mouth, sucking, licking and lapping them until Jane moaned and pulled my face deeper and I licked around the entrance to her hole, running my tongue as deep as it would go into her juicy hot tunnel. I loved the taste of her fluids, pungent but sweet. Her juices were flowing a little more freely now and I learned that sucking on her clit increased the flow.

Aunt Jane pulled my head up and she stared at me, "GOD! You are so damned good, now I need you to fuck me hard. RIGHT NOW!" She rolled me on my back and straddled my slim body. Jane sat erect and pulled her gown over her head and tossed it. She raised herself over my cock and settled downward on my cock. Her hand held me up and guided him inside her wet hot pussy. I liked it. She slowly started to raise up and down over him. The feeling was extreme, I knew I would cum in a second. Auntie was watching me and knew I was going to cum. She leaned away and got something from her bed stand, I couldn't see what she had. She lifted off of me and smiled, "I have a gadget here that will let us have fun longer, it is a cock ring. It goes around the base of your cock and balls and keeps you hard longer and you can fuck longer. You will love it. Now, John, you be still while I adjust it for your size. There! That looks right, how does it feel?"

"Oh, Aunt Jane, it feels good. I like it."

"Good sweetie, now that we are lovers you may call me just Jane, or any pet name you like. Now let me get on top of you again, do you like that?"

"Yes, Sweet Jane, I sure do like it."

Jane mounted me again and my cock felt bigger and harder than ever. She smiled lovingly as she bounced up and down on my cock. She held her breasts to keep them from bouncing too much. Jane leaned forward and stopped moving to let me suck a hard rubbery nipple. I sucked it right in and part of the breast too! I felt her shiver and asked what was wrong, "Nothing, dear, sweet, boy. You just made me cum, a good one too! I love it, I wasn't expecting it, that is the best kind. Are you ready Honey?"

"No Jane, I am fine, I just want to please you."

Jane stopped her movements and placed a little hand on each side of my face, "Oh, sweet boy, love of my life, you please me more than I can believe. Love with you takes me to new heights, way beyond anything I have had before. Now I need to make you cum. Do you want the cock ring off?"

"No, you put it on me, you say when it comes off."

Jane twisted around and lowered her pussy over my face, it was drooling a little and I slurped the fluids in. She shivered again and grabbed my cock and licked around the head before she sucked it in to the hilt. Wow! How could she do that? I didn't know, but I did know I loved it. Her head bobbed on my cock and I knew that this was going to be special. She ran her parted lips and tongue along the length of my cock, then at the base she licked on my scrotum, sucking each ball gently. Then she licked down and speared her pointed tongue into my asshole. She repeated this several times and the pressure in my balls was unbelievable. Jane twisted around again and I looked in her eyes as she loved my cock, she worshiped my cock, kissing and mewing deep in her throat as she kissed and licked, then started over again. Suddenly I knew I was about to cum, I stiffened and said "I'm cumming, I saw her enclose the head of my cock in her mouth, she smiled as I shot a massive load of cum into her beautiful mouth. Her eyes twinkled and the corners of her sweet lips curved up as her mouth filled with my seed. When I was through, she slithered up my body and pressed her lips to mine in a sweet gentle kiss.

I expected to have the cum in my mouth, but no, she slowly let it dribble from her mouth into her cupped hand. She smiled at me, "This is all mine, Lover, it is my daily facial. It keeps my skin soft and supple. I like to sleep with it on my face." She explained as she rubbed it gently into the skin of her face and upper chest. She stood and picked up her gown and put it on, she giggled and got another gown from her dresser. "Here, put this on to sleep in, it is very comfortable and it will make you dream of me tonight."

It was a lovely gown, long, with white silk and pink lace. I looked at her. She smiled gently, "I promise you will love it and I will love to snuggle and cuddle with you all night long in your sweet gown." How could I refuse anything that would please this wonderful goddess? I slipped it over my head. Wow! What a sensation as the silk gown slipped down over my body. I felt an erection growing again. I liked it. Janie giggled, "I know someone that likes how it feels. Come to me, sweetie, we will sleep for a while." Feeling our gowns glide over the other gown was as erotic as putting it on.

I loved feeling our bodies pressed together during the night. I think I had a hard-on all night. I wakened to warm sweet lips pressing against mine. I loved it. "Get up lazybones, we have things to do today." I got up, peed and brushed my teeth. I looked in the mirror at my face, I didn't need to shave. I smiled at how I looked in the gown, the shimmery material fit my hips nicely but the lace bodice looked funny being completely flat.

Back in our bedroom Jane smiled at me, "How did the gown feel Sweetie?"

I rubbed my hands up and down my flanks and then my flat belly. "I like the way it feels. It is very...sexy I guess."

"Do you like feeling 'sexy'?"

"You know I do, I think everything connected to you is sexy."

"Thank you, dear boy. Come with me, I have some things to show you." She took my hand and led me through her dressing room and into her closet. There was a door at the back of her walk-in closet. A wide hallway was ahead of us, a large window was on the right side. She stopped at the window. I looked into the master bed room. Her bed was not three feet in front of us. I looked at her, she smiled, "Charlie loved to watch me with other men. We had an open marriage, I have always had other lovers, I need more sex than one lover can give me." She pulled my face around and gently kissed my lips. "I think you are able to do it though. I haven't felt the need for more than you, my love."

I didn't know what to think or feel. Her warm lips erased everything but thoughts of her soft body, how she feels, how she tastes, and how she sends me to heaven. I accepted whatever she said as being right for us. Nothing could cause my deep love to waver a speck. I noticed several chairs opposite the two way mirror into her room. I looked at her. "He enjoyed bringing a friend or two from time to time. Always with my permission of course."

"Can I bring someone to watch?"

"Yes Dear. That is your decision; YOU do not need my permission, because I belong to you. Charlie belonged to me." She took my hand and led me to another door at the end of the hall. She opened the door and switched on a light. It was another ladies dressing room. There was a well lit make-up table. Rows of wigs. Rack after rack of women's clothes of every description. Shelf after shelf of every kind of ladies shoes, hats, and handbags. She stopped, looked up at me. "Charlie loved to play 'dress up' with me. Would you like to try it? I think most of his things will fit you, my love. Most of it has never been worn, he was too timid to go out in his things as a woman. He was probably right, he could fool no one into thinking he was a girl. You will not go out unless you are a perfect girl. What do you think?"

I looked at her and saw the hope in her eyes; I saw love, hope, and desire. I gave the only possible answer, "I would love to try it, if you think it would please us."

"Sweetie, I think you will love it, I promise that in any of our games I will never do one thing to hurt or embarrass you in any way. Charlie loved to be humiliated and hurt. I do not enjoy doing or watching that. In anything we ever do my love, you are in command. All you need to do is say 'stop'. Everything will stop until you are happy. OK?"

Jane led me out the back of the dressing room and I found myself in my own bedroom closet. She laughed at the expression on my face. Sweet baby boy, please take off the gown and give it to me. Then shave your face and your legs and I'll meet you in Charlie's dressing room in a little while.

I did as I was told and put on a light bath robe and joined her in the dressing room. She looked up from a small pile of clothes on the counter. She walked to me and took my hand. "Come with me Sweetie, I know you cannot try on girl's clothes with a hard-on. Let's jump in bed and get rid of the problem." Jane pulled her gown over her head and grabbed my hand and pulled me on the bed. We reclined on the bed and kissed and caressed each other. I ran my hands over her sweet body, gently touching, softly rubbing, and then tenderly kissing all of her sensitive places. I slipped my hand from her neck, over her breasts, down her slightly curved belly, then cupped her mound, slipping a finger inside her. She was only a little moist, not wet. I put two fingers in her and went a little deeper.

Jane whispered, "Mmmm, that is good, Honey, I love to feel your fingers in my pussy. Play with my clitty too, Sugar. That's right. You are so sweet and gentle when you do that, I love your loving, I think I am wet enough now Lover, put that wonderful cock inside me. OH YES! Easy, now you are all the way in. Damn but you feel good." She started moving against my thrusts and our pelvic areas thumped together time after time. Suddenly she held my hips. I looked at her, she grinned, "I want you behind me, then you can fuck as hard and fast as you want."

She got up on all fours and I moved behind her, my cock slipped in easily. It was good. I started slowly, the feeling was a little different, I liked it. I went a little faster, that was better. Then I got into my rhythm. WOW! That was even better. I was thrusting as deep as possible, pausing at the bottom of the thrust and giving short hard rooting thrusts to get deeper. Jane was grunting with each thrust and began moving her hips up and down a little bit, changing the angle of penetration each time I thrust up inside her. Delightful! I was going to shoot my load soon. We were slapping loudly when we bumped together on each wonderful thrust. I held her hips and yanked her back into me as I thrust forward thumping her hard. I felt the pressure build to a point when there was no stopping, Jane was screaming and so was I. I came so hard I could just gently pump in and out, my head thrown back, then forward and spewing my issue deep inside her. I collapsed beside her and she snuggled into my side softly whimpering. I caught my breath, "Did I hurt you Jane? Are you all right?"

"OH! My sweet baby boy, you are so damned good, so much better than men much older than you are, this is really only about your sixth time and you take me where I have seldom been. I can't wait until you really get going. I can't remember when I have been so thoroughly and completely fucked. I just wanted to get you off so you didn't have a constant hard-on. Now we need to rest for a while."

I dozed off for a while and woke to find Jane beside me. She was staring at me. She softly kissed my lips. She. whispered, "John, Darling, you are my true love forever and ever." She placed a little finger against my lips, "No Dear, you don't have to say a word, I know you love me too. Let's go play 'dress up'."

She led me to the hidden dressing room again. She smiled, "I don't think we will be going out today so we will just experiment a little bit to see how you look. OK?" I nodded and she handed me what appeared to be a fancy jockstrap with a flat lace panel instead of a cup. I stepped into it and Jane told me to pull it up until it was just below my cock. She directed me to spread my legs a little, she reached between my legs and pressed both of my balls upward against my pelvis, I felt one, then the other slip up into a hole in the bone. She pulled my cock and the scrotum up over my balls. She said, "Sweetie, pull the gaff up tight between your legs to hold everything in place. Oh! Beautiful, you look positively girlish down there now! Here, slip on these panties."