Part One can be found here.
The dinner with Diana had gone extraordinarily well. We sat and talked for hours, learning about one another, laughing, telling stories. I told her about my tortuous years in high school and how they had affected my confidence. I didn’t realize until I got home that I had just gone on my first real date, and it was actually fun. Once I found my tongue, there were no awkward silences, I didn’t feel like a nerdy kid. I felt like myself, like a man on a date with a woman. Diana did that to me. She was genuinely interested in what I had to say, she laughed at my jokes, she set me at ease, brought out the best in me and gave me confidence.
When we parted ways, I grabbed her hand and kissed her on the cheek. Even though it came so naturally to me, my heart fluttered wildly in my chest, like a small bird trying to break free from the cage of my ribs. My heart didn’t stop thundering for days. I lay in bed staring into the darkness, replaying every moment, each word spoken, each touch of her fingers on mine, the way her eyes crinkled when she laughed, the hard line of her jaw against her long elegant neck, how she tapped her fingers on the table to emphasize a point.
She had shared with me her wealth of knowledge, a crash course into female sexuality, but what kept my heart drumming over the next week was the promise of more. We had set another date for the following Saturday. I was going to meet her at her home where we would have dinner and sex. Sex. Real sex. I was going to have sex. The words sounded foreign to me, they rolled around in my mouth like marbles, taking up all the room, leaving no room for other words. It was hard to think about anything else. She dominated my thoughts, but Diana warned me not to let any of this get in the way of my school work, saying that if my grades began to slip, she would break it off immediately. I knew she was right, but I also knew it would be hard to focus. What they say about a man’s smaller head is true, sometimes it just takes over.
I was nearly wrecked by the time Saturday finally arrived. I hadn’t slept well Friday night, tossing and turning with the covers jumbled up around me. I even woke up one point and jerked off, a sloppy night time quickie to ease my aching hard on, and was finally able to drift off afterwards. I felt strange getting dressed the next morning, knowing that the clothes I put on would be taken off, discarded lumps on her bedroom floor. Still, I changed three times, tossing sweaters and button up shirts on the floor until I finally found something that felt right, jeans and a plain green sweater. Nothing too fancy, but not the attire of a sloppy college student either.
The walk to her house helped to clear my head. The ancient oak trees guided me along, their drooping branches like her hands on my arm at the restaurant, ushering me forward. The streetlights flicked on one by one as I made my way up her street, mimicking the glow of the romantic candlelit scene of our first meeting, putting me in the right mindset for the evening. The night was cool and the breeze kept me from getting sweaty. I felt good. I was ready.
She opened the door wearing a long black dress, simple and loose, but the fabric clung to her curves as she moved, the hint of a hip showing here, the swell of a breast there. It made her pale skin glow, white against dark, like a starlet in an old movie. Her red lips popped against her face, a tulip rising out of a late spring snowfall. I didn’t know exactly how old she was, much older than me, but she was self-assured in a way that girls my own age were not. Her beauty was much deeper than her appearance; she exuded a confidence that made her glow.
I followed her into the house, watching her glide and sway. I found that I couldn’t keep from looking at her, she was a magnet that my eyes couldn’t resist. I barely noticed her house, a perfect reflection of her style, simple and elegant with muted grays and whites accentuated with splashes of color here and there, clean lines, and understated furniture.
She showed me into the kitchen where she had laid out a cheese board, bread, a tossed salad, and some other finger foods that I didn’t recognize. I felt suddenly out of place in front of the fancy food, thinking a pizza would have sufficed. The nerves hit me all at once, and I didn’t know what to say or do. Diana came to the rescue once again.
She kissed me. She wrapped her arms around my shoulders and pressed her body into mine, and her lips touched mine, soft and wet, alien skin against my own. I didn’t know what to do, so I followed her, parting my lips with hers, reaching my tongue out to meet hers, tentatively at first and then boldly as I found a rhythm. My cock hardened and pressed against the zipper of my jeans. I was embarrassed at first, not knowing if it was appropriate, until she reached her hand down between us and grabbed it through the fabric of my pants. I was startled, thinking I was the one who was supposed to be touching her, learning how to please her.
“There’s something I’d really like to get out of the way,” she mumbled into my mouth before she sunk to her knees in front of me.
She unzipped my fly and pulled my jeans and boxers down to my ankles in one swift motion. My face blushed hot, knowing that she knew it was the first time a woman had seen my cock, and she was eye level with it. She wrapped her lips around it and I jerked, an awkward groan escaping my mouth, the warm wetness of her mouth felt incredible on my sensitive skin. She swirled her tongue around the tip and then took it deeper, sucking harder as she pulled back off of it. She looked up at me as I watched her red lips engulf me, and that’s all it took, ten seconds and I was done. I filled her mouth and, for the first time, felt what it was like to come at someone else’s touch. I grunted, a rather ugly sound I thought, as she swallowed. Even with a mouthful of cock, she was able to smile up at me, and I was ready to do it all over again.
“I’m sorry I was so quick. I di-”
She cut me off, “No need to be sorry, Thomas! I expected nothing different. I just wanted to see what we were working with down there, and it’s quite nice. I’m sure you’ll be ready for more very soon. Now, let’s eat!” her eyes glinted as she wiped the corners of her mouth with her fingers.
Once again, the conversation flowed easily as we ate. She asked me how my first blowjob felt, making me describe the feelings in detail. She explained to me how some women wanted a hand on the back of their heads and for some women, that was a huge turn-off, noting the importance of asking first, getting an idea of what’s okay and what’s not. She told me to be vocal about what feels good. I blushed and almost choked on a piece of Gouda, wondering how she was so open to talking about sex like this.
“Talking about sex is important, Thomas, and it’s hot! How else are you going to know what your partner likes? How will they know what you want if you don’t tell them?”
Her logic was sound, but I just couldn’t imagine myself opening up like that.
“Let’s come back to this later.” she said, gesturing towards the half eaten food. “I think it’s time,” she smiled at me wickedly and grabbed my hand, squeezing it reassuringly as she led me through the door of her bedroom.
“Take my clothes off,” she said softly, her wicked smile still graced the corners of her mouth.
My hands felt heavy as I lifted them to reach towards her. I felt strange, so I kissed her, stalling for a moment to gather myself. I grabbed her around the waist and pressed my mouth to hers, just as she’d kissed me in the kitchen. She moaned into my mouth, pushing her body into mine. I moved my hands down over her hips and slowly lifted the hem of her dress. She raised her arms and I pulled it over her head, revealing only a pair of black lace panties. Her bare breasts were like two tear drops, the soft pale skin almost translucent. I pulled her panties down over her ass, and she laid down on the bed and opened her legs.
“How would you like me to touch you?” I asked timidly, remembering her advice from last Friday.
“Come over here and explore for a bit. I’ll tell you where the good spots are.”
I leaned down in front of her, an eager pupil, and slowly reached my hand towards her, and gently touched the outside of her lips with my fingertip. They were softer than I’d imagined, shaved smooth but for a small patch on her mound.
“Yes, rub me there. Softly. Tease me.” Diana spread her legs wider and pushed her hips into my hand.
I continued to tickle her, moving my fingers up to pull on that little patch of hair. As close as my face was to her, I could see that she was already damp between her folds. I could smell her, an intoxicating mixture of soap and skin and musk. I wasn’t sure what to do next, and I hesitated, looking at the blooming pink flower before me, studying its dips and folds.
“Go ahead, Thomas. Touch me. It’s okay!” she coaxed as she raised her hips towards me, her voice was husky.
With one finger, I swiped from the bottom to the top, where her patch of hair grew.
“Mmm, yes, do that again.”
I did, feeling her wetness coat my finger.
“You’re so wet!” I marveled.
“Mmhmm,” she moaned, and her head fell to the side, her toes squinched the bedsheets. “Spread it around, find my clit.”
I knew where it was from anatomy books and porn videos, but I didn’t know how to go about touching it. Some of the girls on the videos would rub it slowly in circles, some would rub it hard and fast, their faces contorting with effort. I started slowly, rubbing in circles with my fingertips.
“Use the pads of your fingers, that’s it. Now put a finger inside me.”
I couldn’t find her opening at first, it was hidden between layers of slick skin. She grabbed my hand and guided me there, pushing my finger deep inside. My cock leapt to attention at the realization that I had my finger inside a woman. I could feel the damp flesh close around me, her muscles quivered and pulsed.
“Does it hurt?” I didn’t know what to do once inside.
“No, sweetie. You can move it about, wiggle it, push it deeper, fuck me with your hand.”
I moved my finger around, feeling the texture of her flesh change. She bucked and moaned, it seemed like she liked that.
“That was my G-spot. Did you feel that?”
“I think so. I don’t know, you moved, and I lost it.”
“Find it again, and rub it harder.”
I moved my finger around until I felt the same spot, a little rough and bumpy, like where the roof of your mouth meets your front teeth. I pressed my finger upwards to rub it harder and she squealed. I must have looked like such a goof, grinning down at her with wide astonished eyes. She smiled up at me and humped herself on my finger.
“Another. Put another finger in!” She was breathless, her hands went to her breasts and squeezed.
With two fingers inside, I felt like I was going to break her in half, but she was moaning and meeting the thrusts of my hand with her hips, so I didn’t stop. I could feel her pussy tighten around me, like she was trying to hold me inside her. My cock was so hard, I reached down to stroke it through my jeans with my other hand.
“No, use your other hand to rub my clit again. Oh, this feels so good. I’m going to come for you!”
Leaving my aching cock alone, I moved my other hand to her clit and began to rub in circles again. Her breathing began to quicken, and she started grunting and moaning in time to our thrusting, gradually rising in pitch the closer she got to coming. She squealed when she finally orgasmed, clamping her thighs together over my hands, holding me in place while she convulsed. I could feel her muscles rippling around my finger as I watched her, eagerly drinking up her facial expressions, her noises a song I’d been waiting to hear for a long time.
She finally calmed, her breathing slowed, and she reached her arms out, beckoning me towards her. She pulled me in awkwardly between her thighs, her juices smearing on the front of my jeans. I didn’t know what to do with my wet hands, so I held them up off the bed, and she laughed when she saw.
“Oh, Thomas, that was fantastic. Don’t worry about making a mess! We’re only just getting started!” She grinned at me mischievously and reached down between us to grab my hard cock, pressing against her naked pussy, eagerly awaiting what was yet to come.
To be continued!