"The Pass," Seventh Installment of "The Date" series.
Four months later after the disastrous date with Jill at the CW bar and their stupid butt contest, which I was a unwitting contestant, there came a knock on my apartment door. It was after ten on Friday night. I was dozing in front of the TV wearing just my lounge pants. I sat up straight, not sure if I’d dreamt the sound. Then it came again. I got up hesitantly to look through the peep hole. Huh, I thought. It was Jenn, the one who precipitated the breakup at the bar by putting me in a miserable mood. I wondered what she wanted with me. I debated whether I should let her in or not.
I’d had only one date in the last four months, not counting the wedding I attended for a co-worker. As promised, the bride had introduced me to her maid of honor, and talking between official wedding reception duties, wrangled a date with her. It turned out that she had a lot of emotional baggage, breaking up with her boyfriend back from the war with bad PTSD problems. I decided after that first date that I was a poor psychologist, and anything that happened between us physically would make me feel profoundly guilty, and I told her as much. And anything Jenn had to say to me must involve Jill, otherwise, with a boyfriend, she had no need to be here. But after four months, I couldn’t imagine what she wanted. Finally, I opened the door a crack to find out.
“Hi, Ted. Uh, you got a few minutes?”
I eyed her suspiciously. “What’s this about?”
“Can I at least come in?” She seemed put out that I wouldn’t open the door with a warm smile planted on my face. I relented and waved her in, asking if I could get her something to drink. I grabbed a beer from the fridge and poured her a glass, then decided I needed one too. She followed me to the couch in front of the TV. “I’m, uh, concerned that I caused you and Jill to break up.”
Truthfully, she had put a damper on the evening, which had in turn pulled the fun out of the butt contest that I might, I say might, have otherwise enjoyed. “No, don’t blame yourself,” I responded. “I guess I’d had enough of her shenanigans. That butt contest was way over the top.”
“I agree,” she said. “But she’s gotten even worse.”
“How so?” I couldn’t imagine what else she could dream up that we already hadn’t done.
“My first clue was her secrecy. She has never been bashful about telling me all about her sexual exploits. But on this one, she clammed up, denying she was doing anything. So one afternoon, I followed her to a house. I spied on them through the basement windows. She was, um, submitting to domination and sadomasochistic sex play. I watched as two guys would bind her, spank and whip her, pour hot wax all over her, masturbate her with sex toys, have sex with her all the while filming it of course. I found the videos on the internet for sale.”
“Wow,” I said, disheartened.
“Yeah, wow.”
I drew a deep breath and said, “So you think my leaving that night and not communicating with her has pushed her over the deep end?”
“I don’t know.” She looked away, and then took my hand. “But I’m terribly worried about her.”
“Yeah, I guess I am too. What do you propose we do?”
“I guess talk with her. Try to talk some sense into her, that what she’s doing is dangerous.”
I thought about it for a minute, releasing my hand from hers. I was getting a boner, not a good thing with what I was wearing, and the topic at hand. “I guess it wouldn’t hurt to talk things out with her.”
“Oh, thank you, Ted.” She leaned in and kissed me on the lips. Oddly, she lingered for another, longer kiss. “Sorry,” she said, breaking away. I said it was all good. “You know, I often think about how I met you, you know, naked in a cage, and what I did with you, taking turns with Sally jacking you off.” I took her hand and kissed it. Jenn was a brunette with short, layered hair, nice sized tits, not too large, and a nice figure. She was wearing a tight stretch top and the proverbial yoga pants. I wondered why she was bringing that up, and kissing me earlier.
“That’s always been part of the problem,” I said, not releasing her hand. “Whatever Jill wanted to do, I kinda enjoyed it, because it was her ideas, not mine.”
Jenn said, “I know every detail of what you and Jill did together. She liked to talk endlessly about her sex life. She always said you were a good lover, that you could always make her have multiple orgasms.” My cock was at full attention now. She looked at my crotch and smiled. “How long has it been for you, Ted. Hmm?”
Why lie? “Four months and counting.”
She leaned in for a kiss and she parted her lips for me. She reached for my crotch and felt my hard-on, and rubbed me through my sleep wear. “Mmmmm,” she moaned softly into my mouth. She reached under the elastic waistband and grabbed my cock, slowly jacking it. “Feel good?”
It was my turn to moan. “What are we doing?” I whispered between kisses.
“I want you. Tonight. Now.” Her head slipped south and I leaned back. She pulled my pants down and I kicked them off. She took my rigid cock in her mouth and began sucking me off. Her fingers played with my balls. I moaned loudly. It didn’t take long.
“I’m gonna come,” I moaned minutes later. She withdrew my cock from her mouth and lightly jacked me.
“Come for me, baby. Let me see you spurt for the second time.” My cum shot up in the air and landed on my stomach. “Do it, baby, spurt it all out. Oh yeah, oh, good boy.” Pump after pump of my cum drenched my stomach. I hadn’t beat off in weeks.
She got up to get a wash cloth and returned to wipe up my mess. I got on my knees as my cock shrank and buried my face between her legs, trying to sniff her pussy through her yoga pants. I pulled them down to reveal a shaved and engorged pussy. I parted her lips and licked her clit. Now it was her turn to moan. “Jill said you do this sooo good. Make me come, Ted.” I licked and sucked her good. I reached up and felt her tits, still covered. She undid her bra strap, and I slipped my hands under the stretch material to feel up and reveal her tits. She took her top off. God she was beautiful. I pinched her hard nipples. She moaned and bucked her hips to my talented tongue. “Now, I’m coming, Ohhhhh,” she moaned. She squirt her pussy juice into my mouth as she achieved her orgasm. Still I licked her, but she pushed me away. “Enough for the moment, sweetheart. Got to save some for the main act.” She stood, and I followed her to the bedroom, admiring her sweet ass.
She lay down on her back and I kissed her, playing with her right tit and nipple. “You’re beautiful,” I said.
“If I didn’t know better, I’d say you were trying to get in my pants.” She giggled as she pushed my hand away from her breast. I slid it down her firm belly to her moist cleft. I fingered her and she moaned happily.
“Seems you were the one to get in my pants first,” I commented. I alternately stuck my finger into her love hole - and fucked her with it - and slowly rubbed her clit.
“I wanted to find out if you were as good as advertised,” she teased.
“And?”
“Jury’s still out.” She found my cock and massaged it until I was hard again. “I like your cock. Nicely shaped, nice dick head. Long, but not as big as some. It’s nice. Let’s see it in action.” I rolled on top of her and she guided me into her wet cunt. “Ahhhh,” she purred.
I buried it in her and was still. “I saw a program, about how they make dildoes.”
Jenn giggled. “Oh yeah?
“Yeah. They cast a real live hard-on, with a latex mold. The guy has to keep his cock hard with it stuck in this goo for five long minutes.”
“So how’s he do that?”
“He had some help from a naked buxom blond.” We both remained stock still, my cock throbbing in her tight furnace of love. I checked my watch. “Four minutes to go.”
She giggled. “I’d like a cast of your cock, to masturbate by.”
I raised up and frowned at her. “Why do that? You can have me any time you want.”
She brushed the hair from my forehead. “Thank you for that. So, did they make a cast of her sex organ?”
“Oh yeah. When they were done, she takes this dildo and sticks in it her replica pussy.” Jenn laughed out loud. “Okay, it’s been at least five minutes. I’m still hard, I think.”
“Yes, you are. Fuck me good now. I mean it. Long and hard, just like your cock.” I moved my hips and she bucked me hard. I slammed my boner home and she met my thrust. I slid my hands under her butt and squeezed those delicious globes as I pounded her pussy. Having just come, she was in for a ride. After a fashion, I slid a pillow under her ass, my trick for getting dicky to rub her G-spot. She came shortly after, scratching my back in ecstasy. I kept after her, pounding away and she came again, more strongly. “Fuuuuuck! Oh Goooooooood damn, shit.” I felt her uncontrollable contractions on my cock. It felt good to make her come.
I withdrew and rolled her over. She was weak and sweaty from her orgasms, but I got her up on her hands and knees and entered her from behind. I grabbed her luscious hips and slammed her for long minutes. I felt her ass up and lightly spanked her, wanting to gauge her reaction. She moaned and bucked her hips, so I hit her harder, marring the fine skin of her gorgeous ass. She collapsed to the pillow under her hips and I continued my assault on her pussy. I reached beneath her and grabbed her titties, and painfully squeezed them. I couldn’t get enough of her naked body. I rolled her over and she sat up, and sat down facing me. She guided me into her abused pussy. I played with her tits as she rode my cock, straddling my hips. She leaned back, placing her hands on my knees, sticking her breasts up and out for all to enjoy. She bucked madly and came again, soaking my cock and my ass crack with her pussy juice. Panting heavily, she collapsed onto my chest.
“How do you do it?” she gasped. “Last so long?”
“Your mistake was jacking me off,” I grinned.
“My pussy is so soar, I won’t be able to have sex for weeks. We’ve been going at it for 50 minutes.”
“And counting,” I said, my cock still buried in her cunt. She rolled me over on top of her. “Pull it out. I can’t do it anymore.”
I withdrew and turned her over. I grabbed the bottle of K jelly, spread her butt cheeks and quirt the lubrication on her butt crack. ‘No, please don’t do me in the ass,” she pleaded, weak and tired.
“I’m afraid it’s the penalty of not keeping up with my cock,” I murmured in her ear. I put my penis to her butt hole and pressed. She resisted but was no match for my raging hard-on. I was in heat, and needed desperately to possess all of her.
“Ohhhhh,” she wailed, but offered weak resistance as my cock advanced into her forbidden passage. I rested when I was in to the hilt.
“Like the feel of that?” I asked, laying on top of her, stifling all resistance from her.
“It’s so dirty, and I feel panicked. Please pull it out.”
“This your first time?”
“Yes.”
“Just relax, and enjoy.” I withdrew and shoved it back in, over and over. I felt her resistance subside as her anus grew familiar to the penile invasion. I fucked her ass for five minutes before withdrawing. I kissed her ass and licked her anus. “There, all done. Good girl.” I swatted her ass and she yelped. She rolled over and kissed me long and hard . I sat on her, my cock sticking obscenely up in the air. “Jack off for me while I watch.” I pulled the rubber off and tossed it aside. I stroked my cock while I stared at her amazing tits. She massaged her boobs, teasing me.
“You like my tits? Yeah? That’s it, rub your cock, like all you guys do behind bathroom doors. Let me see you do your deepest, darkest secret.” Her voice was husky, sexy. “You’re leaking pre-cum, you horny devil. I want to see you spurt your cum out again. It’s what you dirty little boys do while looking at pictures of naked women, isn’t it?Why don’t you beg me to watch you do yourself.” And I did. She got me going with her dirty talk, and it didn’t take long before I was coming. “Are you going to come now?” she asked sweetly. “Let me see you do it. You’re my boy toy slut, aren’t you? I can make you do anything, because you’re a slut.”
“Oh, god,” I moaned as I felt it rising. Then I spurt. Globs of thick creamy cum boiled out of my abused cock and slowly flowed down my fingers wrapped around my shaft. She watched closely as my cum advanced to her belly.
“Naughty boy, jacking off and squirting cum on to my belly.”
“Damn, that felt good.” I leaned down and kissed her passionately. “Thank you for this, having sex with me. You now own me. I’ll do anything you want, any time. Stay the night, please?”
“Only if you fuck me in the morning,” she giggled.
“Well, gee, I don’t know, I got things to do ….”
“Oh, Is that so?!” she said playfully. She pushed me off and sat up on the bed. “Lie face down across me.” I did as she asked. She spanked my butt, hard. “Now beg me to forgive you.”
“I’m sorry, I was joking. Ouch! I’m begging you to stop spanking me. I’ll be respectful and good to you from now on, I promise.” More slaps assaulted my stinging ass. “Please, now stop!” I wailed. She did, and rubbed my sore bottom.
“You do have a nice ass. Cheeky. Full, nicely shaped, not boney or saggy like a lot of guy’s butts are.” She spread my butt cheeks and fingered my hole. “You seem all healed up. I see the scar from your stitches.” She spit on my ass crack and worked her middle finger up my anus. She fucked me with it. “I can feel your cum gland.” She giggled. With her other hand, she felt my balls. “I can feel the sperm tubes in your nut sack too. And your cum is so creamy white, I love it. I love watching you come.” She withdrew her finger and spanked me some more, then announced she was going to take a shower. I joined her, and luxuriated in washing her naked body. She washed me, too, and slapped my cock as it grew hard again.
In the morning, I got up as quietly as possible so as to not wake sleeping beauty. I walked naked to the bathroom. “Nice butt,” she said sleepily. She’d been sleeping on her stomach, but her head was turned toward me. I stood still, letting her admire my ass. “Okay, you can proceed. Hurry, I need to pee.”
I was brushing my teeth after peeing but she couldn’t wait. She rushed in naked and sat on the toilet and peed while I watched her, slowly brushing my teeth. She wiped and stood, leaned over the sink and brushed her teeth with spare toothbrushes I kept around for just such emergencies. That finished, she kissed me hard on the mouth, feeling my balls up as she did. “Come back to bed,” she ordered. “I’m not done with you yet.”
She had me get on the bed doggy style. She lubed up her fingers and my ass with the jelly and stuck her finger in my anus and fucked me. She got me hard and stroked my cock also. “Do you always fuck your ass when you jack off alone?” she asked, curious.
“Most times, if I do it in the shower.”
“Do you come easier with me fucking your ass?”
“I think I come easier with you just in the same room. Oh, I feel it rising, you make me do it.”
Jenn giggled. “I turn you on that much?”
“Oh fuck, you have no idea, oh, now, I’m gonna come.” Jenn kept her finger up my ass as I spurt.
“I can feel you pulse. Hmm, not too much cum this time. I’m disappointed,” she teased. With her finger in me, I couldn’t pump it out well, so it just flowed out and dribbled to the washcloth she’d placed on the sheets. I squeezed the rest of my cum out running my fingers from the base of my cock to the tip. Jenn scooped it up with her tongue and swallowed it.
“Now, mister, lie down.” I did as she asked. She kneeled over my chest and lowered her sex onto my face. “Lick me, slut boy. Make me come with your tongue.”
“Can I fuck you afterwards?” I licked her delicious pussy lips.
“Ted, I’m sore. I think I’ll have calluses in my vagina from you pounding me last night. I’m afraid that’s all the fucking I can give you for a while.”
“So you’re saying we will fuck again sometime?”
“We’ll see.” I went to town on her clit and she humped my face. I held her hips as she rocked back and forth. She leaned back again, her hands on my thighs. “God you make me hot. I’m going to come.” I sucked on her clit and worked my tongue over it and she came. She squirt her female emissions into my mouth. “Shit, ohhhhhh, ohhhhhh, fuck, fuck.” I licked her more and she came a second time. She rolled off me and placed her head on my shoulder. “I love the way you do oral sex on me.” We lay there and dozed off, naked and spent.
Later that morning, she dressed and headed out. I was still just in the same bottoms I wore last night. At the door, I asked, “I have to know. Jill mentioned you had a boyfriend.”
“We’re having, um, problems, Ted. Let’s just leave it with that.”
“When can I see you again?” I must have sounded desperate.
“Don’t be so needy. Look, you promised to talk with Jill. We don’t know how that will go. Will you two kiss and make up? Or will she throw you out of her life. Let’s wait and see how it goes with her. Then we can talk about us fucking some more.” She patted my crotch and peeked down inside the elastic at my growing cock. “Love your cock. Bye now.” She kissed me and was off. I watched her sachet down the hallway. What an ass. It rivaled Jill’s on the cuteness scale.
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