Painfully Shy, Painfully Awkward

Literotic asexstories – Painfully Shy, Painfully Awkward by Skeeter109,Skeeter109 *Timmy is clearly over the age 18. So is his mom.*

I was worried about my son. He had just turned 18 and was still terribly shy and socially awkward. He was already introverted when his father ran off 4 years ago. After that, the wheels fell off and his self-imposed isolation grew worse and worse. To the best I knew, his only friends were on-line. He had never been on a date, or ever asked a girl out. His life revolved around computer games, Dungeons and Dragons, comic books, and on-line chess.

Yeah, I was worried about him.

I was racked with indecision. Should I talk with him? Let things go on as they are? Try to find a professional for him to talk with? I just didn’t know. Like him, I have always found it difficult to talk about uncomfortable, personal feelings. Conversations involving my private life, particularly sexual issues, have never come easily to me.

After several days of going back and forth in my head, I decided the first step had to be a conversation. If I could get a better understanding of what was going on with him, we could figure out together what to do next.

I went to his bedroom and knocked on the door. “Timmy, can I come in and talk with you?”

There was a brief pause while he came to open the door. I stepped in and sat on the edge of his bed. He sat in his computer chair, facing me while his eyes were glued to the floor.

“I’ve got to tell you, sweetie, I’m worried about you. You seem so isolated, so alone. I never see you go out, hang out with friends at the mall, or go on any dates. What’s going on? Doesn’t any of that have any appeal to you?”

“I don’t want to talk about it!”

I remained quiet and continued looking at him. He was quiet for a few moments and then the words began to tumble out in bunches. “Yeah, I wanna have friends! Yeah, I wanna date girls, but I just don’t know how!”

He slowed down and began talking in a more normal tone. “Whenever I get around girls, my mind just locks up. I can never think of anything to say. I’m afraid anything I say or do is just gonna get laughed at. I couldn’t stand that. I hate my life. I know I need help, but I don’t know where to turn.”

I was racked with confusion. My mind swam with half-formed ideas. After what seemed like ages, I finally settled on what I would offer. I said, “Would you like some help from me?”

Timmy sat there and then slowly nodded his head. His eyes were still glued to the floor. I took a deep breath and said, “Okay. I’m going to try to help you with this. Kick off your shoes and socks.”

After he did so, I pulled him to his feet. I stood there for a moment, looking at him. There was still no eye contact. He looked confused and lost. “Trust me with this,” I said.

With his shoes and socks off, I reached down, grabbed the hem of his T-shirt, and helped him pull it over his head. I rested my hands on his chest and then slowly slid both hands down to his belt buckle. I undid his belt. I moved to the button on his jeans, popped it open, and eased his zipper down. I pushed his jeans passed his hips and they fell to his ankles. “Slip off your jeans and sit on the bed.”

He steadied himself with a hand on my shoulder and did as I instructed. When he was settled on the bed, I stood in front of him and began to undo the buttons of my blouse. When I reached the last button, I shrugged it off. Although he couldn’t make eye contact, he was now staring at my chest. I could see his eyes widen and he couldn’t take his eyes off my bra-clad tits. I let him look. I’ve always been a full-breasted woman but, to be honest, they had begun to sag just a bit although they still kept a nice shape. I let him stare for a few seconds and then hunched my shoulders, reached back, unhooked my bra, and let it fall. I straightened up and let him take in the sight of my bare breasts. I have large brown aureolas and thick, prominent nipples. I could feel my aureolas crinkle and my nipples harden.

I reached behind to unzip my skirt. This had the effect of lifting my breasts up and Timmy could not take his eyes off of them. I struggled with the zipper and then stepped forward and turned my back to him. “Help me with my zipper, please.”

He fumbled for the tab and I could hear and feel the zipper come down. My skirt fell. I stepped out and turned to face him. I had put on a few pounds over the years and had developed small love-handles and a little buddha belly. It was nothing extreme, but I felt self-conscious and awkward. I stood there for a moment, drew in a deep breath, slipped my thumbs under the waistband of my panties, and peeled them down.

I stood back up and let him look. My bush was light brown and wispy, just covering the mound over my pussy. There is no need for me to trim it, so I don’t. Standing there, he could see the the beginning of the slit at the very top on my pussy. While he was staring at me, I looked at his lap. His cock was erect and poking through the opening in his boxers. It was visibly throbbing and looked painfully purple. It was about seven inches and proportionate in girth. I could see a bubble of pre-cum leaking out.

I caressed his cheek and sat down beside him. I rubbed his back for a few seconds, slid behind him, and lay back. I pulled my heels up to my ass cheeks and separated my knees to form a cradle. I could feel my pussy oozing juice. “Take your boxers off and come lie on top of me.”

He lifted his hips and slid his boxers off. He turned, crawled between my legs, and settled in with his face nestled in my neck. “Raise up your hips a little.”

I reached down between our bodies, took his cock in my fingers, and rubbed the pre-cum over the head of his dick with my thumb. I brought his dick to my opening. As soon as his cock touched the entrance of my pussy, his body went rigid and his breathing got ragged. His dick began to jerk in my fingers and I felt ropes of cum splash the outside of my pussy. “Mom! I can’t help… I… OHH!… AHH!… UNH! … UNH!… unh.”

His body went limp in my arms. “I’m sorry! I’m sorry! I’m so, so sorry.”

I didn’t know what to say. I lay there with him on top of me. I kissed the top of his head and rubbed his back. We were still for a few moments and I could feel the spunk trickling down the crack of my ass. I screwed up my courage and decided to say something. “Sweetie, I know its hard for you to believe right now, but it’s all okay. You got excited, is all. I know you’re embarrassed, but everything will work out. You’ll see.”

We lay there for a few more moments. both afraid to say anything. “I have to clean up, honey. You made a mess on me. Please hand me some tissue.”

He sat up, grabbed a wad of tissue from the bedstead, and passed it to me. He slumped there with his elbows on his knees, staring at the floor. I took the kleenex and cleaned myself as best I could.

I lay there for a moment with him sitting beside me. I took a deep breath and stood up. “I’m going to take a shower. You need one, too. Come on with me.”

I took his hand and led him to to his bathroom. I leaned down, turned on the water, and adjusted the temperature. Still holding his hand, I stepped into the shower. He followed behind. His back was to the shower head. I turned to face him. He was still staring at the floor. I hugged him around the waist, pressing my body full against his. I reached behind him and soaped up a shower scrubby.

I began to wash the front of my body, under my breasts, and between my legs and ass. I rinsed the scrubby, re-soaped it, and began to wash his chest. My hands trailed down to his cock and I gently washed his genitals, He began to swell and thicken. I had him turn around so I could wash his back. When I reached his ass, I washed that, too. My finger slid over his butt hole and I massaged it.

When I was through, I dropped the scrubby, reached around, and found his dick. It was hard now and I began to masturbate him. My tits were pressing into his back and my bush was brushing the back of his thighs. After a few strokes I stopped and turned around. I bent at the waist and braced a hand on the back wall of the shower. I separated my feet. “Step in close behind me.”

When the front of his thighs were touching the back of mine, I reached back with my free hand, pulled him forward, and once again placed his cock at the entrance to my pussy. His hands were resting on the small of my back. “Press in a little.”

He eased forward and I guided him in. I gasped as his cock head spread my pussy lips and began to enter me. Timmy froze. “Mom? Are you all right?”

I gathered myself and huffed out, “I’m okay, sweetie. Please don’t stop.”

I could feel the walls of my pussy stretch to accommodate his girth. He slid in slowly. He moaned as his dick made its way up my pussy, pressing in and filling me. I felt his hips touch my ass. I groaned, “Unhh!” I caught my breath and adjusted to his size. “Now, pull half-way out and push back in.”

I didn’t have to repeat myself. He began pulling back and pushing in without any further encouragement. Every time he pushed in, the air rushed out of my lungs. I was grunting with each thrust. “Guh….. unh…. unh…. ooph…. ooh… unh… unh… ahh.. unh.. unh.. unh. unh. hunh. unh.”

His thrusts were becoming more and more urgent. My tits were swinging wildly under me. His hands were now on my hips, pulling me back as he shoved himself in. His breathing got ragged and he started to pant. There was one last push and he held me there with my ass pulled tightly back against his hips, fully impaled. “MOM? MOM!”

“It’s all right, sweetie! Let it go! Let it all come into me!”

“AAHHH!… AHHH!… Ahhh!… ahh.”

I felt his cock pulsing and knew he was filling my belly with spunk.

We both rested for a few seconds, catching our breath, and then I slowly stood up and his softening dick plopped out of me. We switched places and I rinsed off the cum that was now dripping down my thighs. Timmy hugged me from behind, his dick dangling in the crack of my ass while I cleaned myself.

We stepped out of the shower, helped each other dry off, and I led him back to his bedroom. We crawled into bed and settled in. I was lying on my back and Timmy was on his side with his head resting in the crook of my shoulder and his cheek resting on the top of my breast. “Mom?”

“Yes, sweetie?”

“Thanks.”

A quick smile crossed my lips. “You’re welcome. Now let’s get some sleep.”

I laid there for a while, but no hint of sleep came. “Sweetie? Are you still awake?”

“Yeah.”

“I can’t sleep. I’m too… tense. I have some… feelings I need to take care of. Would it be okay if I took care of those feelings while you lay here with me?”

There was a brief silence. “Sure, Mom.”

I lay still for a moment, screwed up my resolve, and let my hand drift down my tummy. I encountered Timmy’s hand as I was moving down. I hugged him tight and squeezed his hand.”Thank you.”

My hand continued it’s journey until it brushed my pussy hair. I played with my hair a bit, pulling it and caressing the mound where it grew. The caresses gradually became a massage. Timmy lay there quietly and I could hear him breathing. There was a pale moonlight coming in through the window and I knew he was looking at what I was doing with my hand.

My fingers slipped down further and reached my pussy lips. They were engorged and slick with juice. I slid my middle finger down to the slit and I coated it with the lubrication I found there. I ran my finger up to my clit. I wanted easier access, so I splayed my legs apart. Timmy laid his top leg across mine. I started with long, slow strokes along the side of my clit. My ass cheeks began to tighten and relax rhythmically, making my hips hunch up and down. My finger slid back down to my pussy. I pushed my middle finger inside three… four… five times, my hips rising to meet each finger thrust.

I ran my finger back up to my clit and began rubbing in circles. My hips began pumping more frantically and my breathing became ragged. I pulled Timmy close. “Suck my nipple!”

Timmy latched on and began sucking. He placed his hand on my wrist so he could feel my frenzied hand movement. My toes curled back and my back arched. I hung there, frantically rubbing my clit. A sweat broke out on my forehead, the dam burst, and I began grunting out my orgasm. “I’m!… I’m!… OHH!… UNHH!… UNHH!… Ahh!… Ahh!… Ah.”

After the initial wave of spasms passed, I lay there with my finger pressed against my clit. An occasional shiver ran through me. I caressed Timmy’s hair and he released my nipple. I lay there for a few moments, luxuriating in the afterglow of my orgasm. I kissed the top of Timmy’s head. “That was so good, sweetie. Being here with you made it special. Let’s try to get some sleep now.”

I woke up just as the sky was beginning to lighten. We were both lying on our sides and Timmy was fast asleep. I was pulled up close behind him with my arm draped over his waist, my hand resting on his erect cock. I pulled my had to my mouth, licked it, and began to slowly and gently masturbate him as he woke up.