First Date
I met Jill through a friend. I was relatively new to the state, having moved to the big city after college to take the job I was offered. I was living in an apartment complex, and met Tommy out in the parking lot, both of us working on our near identical Mustangs.
I was really hard up. My girlfriend of two and a half years in college broke up with me; she still had another year of school left. It had been about six months since I’d had sex. Jill was a petite young woman my age, with straight brown hair and wore glasses too big for her face, which was cute as it lent an air of librarian authority to her. We set up a date to attend the state fair the next weekend.
It was late August, the evening clear and warm, dusk upon us. We paid for our tickets and walked into the fair grounds. Jill put her right hand in my right back pocket. She could now feel my butt cheek up as I walked. This was a great sign for things to come later that Saturday night. Every moment she got, her hand was on my butt cheek. Having our fill of rides, climaxing with a helicopter ride - a rickety, vibrating old machine which I expected to fall out of the sky at any moment - we left for my apartment.
Back home, we cracked a few beers and eventually ended up lying in my bed talking and kissing. I rolled and lay on my back, and with my arm under her head, pulled her to rest her head on my chest. With a little downward pressure on the back of her head, she asked, “What can I do for you, sir?”
I replied, “You know.” She proceeded to undo my belt buckle, jeans button, and unzip my pants. I raised my butt up and she lowered my pants to my knees. She stuck her fingers an inch beneath the band of my underwear and swiped her hand three times across my flat belly, my hard-on very apparent in the soft lighting of the bedroom. Then she lowered my underwear down to where my jeans were.
“You have a very nice body,” she said, “broad shoulders, slim waist ….” She stood my cock straight up. I suspected a hand job was in the offing, a very nice act on a first date. Instead, resting her head on my stomach, she put my cock in her mouth. Whoa! This was much more than I expected. Now, I’ve had hand and blow jobs before, but they all paled in comparison to this woman’s treatment of my very erect dick.
Usually when I have sex, I last around 45 minutes. After the initial mad humping, I slow down. After the initial excitement, I luxuriate in the sex process, making myself last. But the act she was perpetrating on my penis was a whole different animal. Jill had the exact pressure, the exact suction down to a science. In two minutes of pure ecstasy, I humped and shot my load into her mouth. Then she swallowed my mess! “Oh my god, that was sooo good,” I crowed.
She snuggled up against my shoulder, and said, “I swallowed.”
I kissed her, and then frenched her. “That was awesome.” I knew better than to ask her where she learned to do that so well. It was obvious she’s been around the block a number of times more than what would be termed healthy. Conscious that my cock was flagging, I rolled over. Her hand drifted to my butt and she fondled that erotic flesh.
“You have a very nice ass,” she commented. “Cheeky.”
“Thank you.”
As she idly rubbed and probed, she asked, “You ever think about being tied up?”
My mind screamed at me, ‘Definitely not on the first date!.’ “No, not really. What do you have in mind?”
“I’ll show you.” She sat up and got off the bed. She removed my socks and jeans and underwear, then took my shirt off. I was now totally naked. “Roll over.” I did as she directed, conscious of my shriveled up cock. She started stripping her clothes off. Down to her underwear, she quickly removed her bra and panties. She had smallish tits and a nice bush between her legs. She went to her purse and dug out several lengths of rope.
“Ah, look, Jill, I don’t think-“
“Get up.” I got off the bed and she lay down spread eagle. “Now tie me up.”
“Oh. Okay then.” I took the ropes and tied her wrists and ankles to the bed frame. She moaned in anticipation. Seeing her like this made me hard again. With a boner, I lightly brushed her tits and nipples, making them hard. I licked and sucked on them. I looked at her wide open, glistening pussy. “You’re wet.” She moaned in response. I got between her legs and licked her pussy all over and then concentrated on her clit. She moaned louder, and bucked her hips. I rode her, my mouth clamped to her sex, licking away.
“I’m gonna cum,” she moaned over and over. I placed my hands under her ass and massaged her erotic flesh. She tensed, then orgasmed. She bucked wildly, releasing more of her sex juice. I lapped it up. “Fuck me now. Please fuck me.” She watched me as I knelt over her naked and glistening body, my cock hard and throbbing for her. As I rolled the condom down my shaft, I thought to myself, she was in for one hell of a ride. Once I cum, I can literally last hours before spurting again. “Do me good,” she pleaded.
I entered her steaming pussy and shoved my cock in to the hilt. I’m probably of average girth, however I am long, and I sank all the way in, bumping her cervix. I lay on top of her not moving. She shuddered, her head rolling back and forth, moaning in frustration. She waited as long as she could before bucking her hips. “Fuck me now. Hump me good.” I slowly withdrew my cock and rammed it back in hard. She gasped. I picked up the pace and she met my thrusts. “Damn, shit that’s good.” It couldn’t have been a minute later that she had another orgasm. Jill arched her back and moaned loudly. I could feel her contractions on my hard cock. Her female emissions ran down my balls as I planted myself deep as she came. We went at it madly for another quarter hour or so until I could tell she was tiring. I grabbed a pillow and jammed it under her butt. I knelt and continued to thrust my hard cock into her love hole. In and out, my cock head rubbed her “G” spot. She squealed as she came a third time, sweat pouring off her gloriously exposed naked body. Then she collapsed, exhausted. We’d been going at it for a total of about 25 minutes.
I untied her and coaxed her into turning over. I retied her to the bed. “What are you going to do?” She asked anxiously. I didn’t respond. I put the pillow under her hips so her ass was sticking somewhat up in the air. I’d already pulled the condom off and pointed my cock head to her anus. As she felt my male weapon on her pooper, she scrunched her butt and said, “No, don’t do me there.”
“I’ve had two of your holes tonight, I aim to have all three. A hat trick, so to speak. Hockey players do it with goals, I do it with holes.” She didn’t find me amusing.
“I’ve never had anal sex before,” she complained.
“You just might like it,” I said. I reached for the Vaseline jar, and lubed up her anus and my cock. I pressed at her opening. She resisted, and I spanked her butt. “Relax,” I demanded. I made progress but she kept resisting and complaining. I spanked her cute butt some more. She wimpered. Then I was past her sphincter. She went rigid in panic, but was helpless to stop me from fully burying my cock up her ass and deep into her bowels. She let out a long wailing cry. I spanked her again, enjoying abusing her butt and my domination over her body. Once buried to the hilt, I slowly withdrew, and reinserted my cock. I did this about ten times until she relaxed and accepted the ass fucking. I’d done it. I’d fucked all three of her holes.
As I felt myself start to climax, I withdrew my cock. I untied her and turned her on her back, putting a pillow under her head. I straddled her and began jacking off. “Watch me spurt my cum.”
In a daze, she watched me jack off. “Cum for me, baby,” she murmured. “I want to see your beautiful cock shoot your cum.” A few moments later, I spurt, shooting an ample amount of my seed onto her breasts. When I was finished, she took my cock and pulled me to her mouth. She squeezed the remaining cum out of my cock and it dripped into her open mouth. “I love eating your cum,” she said smiling
.
“And I love fucking you.” She smiled and stretched luxuriously. “You know what I would really like? I want to do a threesome.”
I smiled. “You have a girlfriend in mind?”
“No, silly. I mean with two guys.”
“Can I watch?”
She giggled. “No, just you and another guy.”
“And just where do you want my cock? Hmmm?”
“In my mouth. I love your hard cock. It’s so perfect. It’s cut, has a delicious cock head, and it’s long. Just right for my mouth.”
“And ass,” I said. “You know what I’d like? I’d like to see three guys do you all at once.”
She seemed to consider that and then said, “Yeah, I could do that. Three cocks servicing all my holes at once. The thought of that is making me horny all over again.”
