I was just over 19 when my mom died of cancer. She was just 38 and it was a long slow and horrible process to watch her die and I had a hard time with it. I was attending a small community college and was working a part-time job but didn’t earn enough to pay rent so my mom’s best friend Charlene, whom I had always called my Aunt, offered to let me move in to her spare room. She was the same age as my mom and because of her closeness to my mom and also because her husband had died two years earlier, she knew what I was going through. At first she let me have my space and didn’t get on my case if I came home and just drank myself into oblivion. It was one of these nights that it happened though.
I got home early – about 4PM on a Friday before Charlene got off work and the quietness of the house was too much to handle. I went down to the liquor store and bought a fifth of vodka and went back to the house and began to drink alone. It was about 7 when Charlene got home and I was already plastered. I was sitting alone in the dark sobbing and she could tell I was hurting more than I let on when I wasn’t sober. I had taken my shirt and pants off because it was hot and was wearing a pair of silk boxers. I had gotten up to pee a few minutes before she arrived and had been too drunk to button the boxers back up. I don’t remember much except that I know my member was poking out and she discretely put a blanket over my lap and sat down to talk to me. I let it all out. I cried for over an hour and told her how I missed my mom and how lonely I was inside and she just listened to me and held me with my head on her shoulder. I passed out several times and finally she led me to her bedroom to sleep it off in her bed because mine was upstairs and I was in no condition to go up a flight of stairs. I crashed on her bed.
I woke up at about 1AM and my head was spinning. I walked into the bathroom to find some aspirin and came back to bed. I hadn’t realized it when I got up but Charlene was lying in the bed beside me. She was evidently having a hard time herself because there was an empty bottle of wine on the bedside table, one that I had attempted to open in my drunkeness and couldn’t. She must have drank the whole think. My head was still spinning and I knew that I should try and make it to my own room but I didn’t make it past the door before I felt like I was going to pass out again so I just laid down beside Charlene in her bed. I looked over at her, she was on her side with her back to me and the bright moon outside cast a line of light on her sillohuette. She was very crevaceous with a trim waistline and wide hips. I could see her move slightly with every breath. This was a close as I had ever been to a woman and the sight of her was making me hard as a rock.
It started out very innocently, I just wanted to give her a thank you hug. She was wearing one of her husband’s old t-shirts that went down to her knees and a pair of cut off sweat pants. I hugged her but kept on holding on for a few minutes. It just felt good to hold something and I needed to be held back. My right arm was around her and I didn’t notice it at first but the palm of my hand was resting on the top of her left breast. She shifted a little in her sleep and I realized my fingers were only inches away from her nipple. I slowly reached out with my finger, not daring to touch her completely, holding the tip of my finger just above her soft nipple, then I touched it through her shirt, rubbing softly until it began to stand erect between by finger tips. She stirred again beneath my touch and I thought she was going to wake up but she didn’t. I began to gently caress her arm with tender gentle strokes and every so often I would stroke her breasts and nipples. I carressed the length of her arm down along her side to her hand which rested on her hip, where I began to carress as well.
At first, I just stroked the top of her hip along her leg but then I slowly found myself moving to her thighs. I carefully moved my hand underneath her shirt where I stroked her soft belly to the edge of the waistline of her cutoffs. She still hadn’t moved and I became a little bolder and let my hand wander down her thighs, touching her ever so slightly. I wandered over her soft mound once or twice but was hesitant to touch it too much for fear of waking her up. I moved back up to her belly under her shirt from her belly button up to her arms, which blocked my path to her large plump breasts. I continued to stroke her belly down to her waistline and I buried my nose in her hair. It smelled pretty and before I knew it I had slipped my hand under her waistband and was now playing with the lace of her panies.
My mouth was dry and I was afraid the beating of my heart would wake her up. Slowly, I caressed her thighs and could feel her soft mound of pubic hair beneath her panties. My hand meandered back up to the waist band of her panties and then underneath them, probing in the dark. He pubic hair was coarse and bristly to my touch and I stroked it gently with just my index finger, back and forth at first then my fingers began to search deeper into her fold and my middle finger slipped into a sudden wetness between the folds in her skin. The tip of my finger felt for the very first time her soft inner flesh when she rolled over on her back. Her movement startled me and I began to remove my hand but she stopped me, gently kissing my forehead she whispered “It’s OK. I’ve been awake since you got up to pee.” Her hand guided mine back down to her soft pussy as she taught me how to touch her. She looked me in the eyes, and kissed me on the lips, gently and softly. I could taste the wine on her tongue as she gently probed inside my mouth.
My cock was so hard it hurt and she guided my hand to her clit and told me what it was. She still had on all her clothes but as I fingered her soft juicy pussy, she pushed her shorts off her hips and then I let her slide them all the way off. Next I helped her pull the t-shirt off her head and she let me look at her in the moonlight. She carressed my chest softly and played with my nipple and guided my had back to her pussy. With my other hand I began to fondle her breasts again, rolling her nipples between my fingertips. She was stroking my hair and kissing me softly and then her hand moved slowly, back and forth over my chest, down to my belly button and finally to my waist band. She rubbed my cock over my boxers then slipped her hand inside. Her soft touch caressed my hard cock and I not being able to take it anymore, I exploded all over her hand. Embarrassed I apologized to her.
“It’s your first time, isn’t it?” She said.
“Yes – I’m so sorry!” I relplied sheepishly.
“Oh baby doll, there is nothing to be sorry about! It’s OK. Keep on going.”
She held me tight against her and I kissed her cheek and then her lips and down her neck to her breasts which I cupped and fondled as she moaned. I let my other hand go back to her pussy and began to fuck her with my fingers. She arched her back against my touch and I began to kiss down towards her stomach and around her belly button. Soon, I began to lick down towards her pussy and I wanted desperately to see what she tasted like.
I kissed her pubic hair and I could smell her sweet musky womaness emmanating from the folds of ther pussy. I began to kiss her thighs, still fingering her and worked my way back up to her clit. I could taste her juice as I fingered her and now began to work on her clit with my tongue. She was now writhing and squirming beneath me, every time my fingers probed her wetness she tried to pull them in farther. I was getting hard again and then she began to moan
“Yes – oh baby, oh baby – keep going.”
Then her whole body shuddered and I felt her pussy grab my fingers as she spasmed involuntarily to her orgasm. She was breathing heavy and she reached over and gently began to coax my cock back to full length.
“I want you inside me” she moaned into my ear, gently guiding my to her.
She pulled both legs up in the air and opened her pussy for me, I could see it glistening in the moonlight and I was able to find it easily. Her calves were resting on my shoulders and I placed the head of my cock gently in her opening and began to stroke. She was warm and tight, but I fit in perfectly and soon, I was fucking her with all the length of my cock. I was stroking deeply when she arched her back to me again and began to play with her clit and I felt her spasm with another powerful orgasm. I could feel mine coming to and I told her “I’m going to come again, I’m going to come again!”
“Do it inside me baby, inside me!” and with that I could stroked her as fast and has hard as I could until I exploded deep inside her warm pussy. “Oh yes baby yes!” She cried out.
Totally spent, I laid on the bed beside her and stroked her hair and kissed her cheek. She took me in her arms and kissed me again.
“I love you Charlene – I really do.” I whispered to her. Our naked bodies still pressed tightly together.
“I love you too baby.” She said back to me.
From then on, I never bothered sleeping in the upstairs room again. That was seven years ago. Since then, we repeated this same scenario often, and though I have missed my mother from time to time, the hurt is gone now and I have Charlene to thank for that everyday.