Sorry for the long wait. I had some IRL stuff that popped up and I didn't have a lot of getDare time for a couple of weeks. I should be back on schedule now.
Chapter 33
I said, "Yes," and rolled over to the edge of the bed. I had bought condoms months ago at the start of the school year but I hadn't had the opportunity to use one. Well, I did masturbate in one to see what it felt like but I digress. I opened top drawer on the night stand next to my bed and pulled out a tin that used to be full of candy but now contained ribbons of Trojan Her Pleasure Sensations condoms with Armor spermicidal lubricant. I opened the tin and ripped one condom from the end of a ribbon. Then I closed the tin and put it back in the night stand.
As I ripped open the pouch, Lindsay asked, "Can I put it on?"
"Of course," I answered, handing her the rubbery ring and tossing the empty paper pouch to the floor.
I got up on my knees on the bed and faced her. Lindsay stroked my dick twice and then placed the ring on the tip and started pushing at the edges to roll it down my penis. Lindsay was struggling to roll it on and it was very constricting on my dick. I realized at that time that condoms weren't supposed to be this tight and I decided I would buy Magnums next time.
"Sorry, I didn't know I had a big dick when I bought these," I said.
Lindsay laughed. Eventually, she got the condom to roll all the way down my penis. Then she laid back down on her back. I grabbed her panties by the sides and she lifted her hips so I could remove them. Then I laid down on my side next to her and placed a hand on the front of her pelvis, feeling her closely trimmed pubic hair shaved into a triangle.
Lindsay looked me in the eyes, "Pat, I'm a virgin."
"I know. I am too."
"Yeah, I know. I'm just saying to go slow and be gentle."
"I will."
I slid my hand down and used my middle finger to part her labia. She was already soaking wet. As my finger rubbed against her clit, she threw her head back and arched her back up off the bed. I ran my finger up and down the length of her slit and she started to moan, "uhn . . . uhn." Then I pressed the tip of my finger into her vagina. She was so wet and warm and soft. She shivered and let out an "ohhhh." I wanted my dick inside her.
I removed my hand from her and climbed on top of her. I looked into her eyes and used my right hand to guide my penis. I parted her labia with the tip of my penis and began sliding it up and down the length of her slit. She closed her eyes and began to pant, "ah ah ah." She quivered each time the tip of my dick touched her clit. I could feel that she was getting wetter with the back of my hand. Her juices began to run into my sheets.
Then I slid the tip of my dick into her vagina. Once I had the tip lined up, I placed both hands on the bed and began to push. I tried to push gently but she was so tight and I was so hard that I wasn't making any progress. Slowly, I pushed a little bit harder and then a little harder still. Lindsay's noises went like, "Ahhhhh, ah . . . ah . . . ow . . . ah! Ow . . . ow! Pat, stop."
I stopped pushing. Not even the entire head of my dick was inside Lindsay yet, less than an inch. Lindsay said to me, "I'm sorry Pat, you're too big. It hurts. I'm not ready for this yet. I'm sorry."
I pulled my dick out of her. "It's okay Lindsay," I told her, "I don't want you to do something that doesn't feel right."
"Um, could you go back to fingering me with the tip of your dick?" Lindsay asked bashfully.
I smiled at her, "Okay."
She reached down with both hands to the base of my dick and rolled the condom back up the length of my penis. "You won't be needing this."
I grabbed the now bare shaft of my dick. It was simultaneously more sensitive and comfortable to be free of that constricting latex. I went back to work, up and down Lindsay's slit, with the bare tip of my cock.
Lindsay's head fell back against the pillow. She closed her eyes. "Uhnnn, oh yeahhh. That feels better. Uhhh. I love your dick."
I played with different rhythms and strokes, trying to find what made Lindsay squirm the most. I tried long, short, and circular strokes at fast and slow speeds. I found that making small circles with the tip of my dick on Lindsay's clit worked the best. I started out slow and very slowly built speed. Lindsay's hips were gyrating. Her arms were moving about, first out to the side to grab hold of the sheets, then to the sides of her head to run her fingers through and grab hold of her hair, then to my chest or my side, then some combination of the three, and so on.
The tiny circles reached a fever pitch. Lindsay's juices soaked her entire crotch at this point. Her right hand grabbed my left wrist tightly; her left hand grabbed a fist full of sheets; and her entire body quaked fiercely. She gasped, "Uh uh uh, Gahhhhhhhhhd."
Then she collapsed on the bed, motionless except for her deep breaths. I rolled off of her and laid on the bed next to her. She turned her head, looking me in the eyes, and said, "Oh my god, what was that?" She stopped to breathe heavily and then continued, "You are amazing. Thank you for that."