This is a print version of story The Homely 18-Year Old Babysitter by otter3440 from xHamster.com
The Homely 18-Year Old Babysitter
I had been a single father for three years now. I had lost my beautiful wife in a tragic car accident. I had reared my 5-year old daughter single-handily. I was so traumatized by the death of my wife that I had not dated since her passing. Yet, recently, at the urging of friends, I had joined Match.com and had been on a string of dates and one-night stands. I had hired an 18-year old named Lacy to take care of my 5-year old daughter. She was very good with the c***d and I paid her handsomely for her efforts. Lacy was a very homely girl with a severe case of acne. As a result, in my dealings with her, she was very shy and made little eye contact. Yet, from the neck down she had the body of a nubile Goddess...pert, mouthful sized tits, a tiny waist line and ass cheeks the size of a couple of g****fruits. She couldn't have weighed more than 80-pounds.
I had hired Lacy that Friday night to work from 6 PM to 2 AM. I planned on taking my date out for for dinner, a movie and hopefully a fucking at her place. After dinner, my date didn't feel well so I took a rain check and dropped her off. I arrived back home and was greeted at the door by a surprised Lacy who expected me to be home much later. She had put my daughter to bed a half hour earlier and it was apparent by her puffy eyes and running mascara that she had been crying. Concerned, I took her hand and guided her to the couch where we sat down together. I asked her what was troubling her and it all spilled out with a fresh river of tears. She confessed that she was heart broken that the boys never paid her any attention because she was so ugly and that she had never even kissed a boy. I was touched by her honesty and aroused by her innocence. So, I put my arm around her and whispered in her ear whether she could keep a secret and then I turned her face towards mine for that acknowledgment. She nodded yes and then I simply pressed my lips against hers and softly kissed her lips. Soon our tongues were exploring eachother's wet mouths and I grabbed her and lifted her up on top of me. The kissing continued passionately while I slipped my hands under her summer dress to cup her tiny ass cheeks. She let out a lustful groan as I caressed them and slipped my middle finger under her cotton panties to press against her musky anus. By now I told her to pull her dress down and remove her bra to expose her magnificent, mouthful sized tits showing off her half-inch long, erect nipples. I suckled them like a newborn while my hands worked her ass crack and my throbbing cock slowly dry humped her pussy. After an hour, I pulled her off me and placed a pillow under her head and had her arch her ass in the air on all fours. I then removed her dress leaving only her cotton panties on...knowing full well that her two virginal holes would be shortly exposed for my tongue and cock. My mouth was agape. Her teen ass was less than the width of a ruler and the area around her pussy had drenched her cotton panties. In a fit of uncontrollable lust I grabbed her panties and tore them asunder to expose the majority of her ass meat, but more importantly, her miniature pussy and pea-sized anus and even smaller slit. I proceeded to cup her left ass cheek with my hands as my right pinky finger spanked her glistening asshole while I went About French kissing her ass cheek. At this point her ass involuntarily began to twitch with excitement. After 15 minutes I ended up kissing her on her perineum, the highly sensitive flap of skin separating her anus from her pussy. I made extra loud kissing sounds as I peppered it with kisses. By now my nostrils were flaring like a horse's as they were pinned against her miniature anus. I made sure to make loud sniffing noises as I took in her musky anal scent. This girl took good care of herself because her anus smelled so, so good. I then crossed over to her right cheek and dined on it with equal passion. Again, I returned to her perineum, but this time I headed north. I paused and told her she was about to receive her first anal kiss. But, I told her that I wanted it to be memorable for the both of us by having her pucker it in anticipation. I watched for the next 5-minutes with my hands clamped on her ass cheeks her tiny little rosebud flexing and puckering...awaiting my lips to meet it as it puckered outward. With perfect timing that is what occurred. I could feel it pucker outward to meet my lips. Soon, my loud topical kisses gave way to my gifted tongue. Before my tongue made a full revolution around her virginal asshole, out of her pussy shot a rope of her cum. I quickly hermetically sealed her pussy lips with my mouth to ensure that every last drop went down my throat. It seemed to never end as I would pull away for a gasp of breath, another rope of juice would coat my face. Afterwards, she collapsed, but I pulled her back up to finish my rim job. Finally, after eating her asshole out for another half hour I flipped her over to feast on her drenched pussy. She was incredibly limber and placed her legs behind her head. I then went to work teasing her little juice hole by kissing and licking her pussy everywhere but her swollen clit. She was whimpering in delight as I finally began to feather lick her clit. Maybe 20-seconds elapsed before she started squirting again. I sealed her lips with my mouth again and opened my esophagus to receive another river of her love juice down my throat. I shared the last mouthful with her with a passionate French kiss. I then got up and slow stripped in front of her until I was down to my boxers. Her eyes lit up from the outline of my sideways erection. I then dropped a throw pillow on the floor and told her to get on her knees. Just inches from her face I pulled down my boxers and out popped my 8-inch cock. She instinctively grabbed it and caressed it with marveled eyes. Finally, she pulled it down and wrapped her virginal lips around the head and several inches of my shaft. This time I let out a visceral groan. Even though she was tough to look at, I wanted to build her confidence, so I told her she had beautiful eyes and how important it was to make steady eye contact while sucking a man's cock. Soon, more and more of my cock was disappearing in her mouth until finally, with new tears welling, my entire shaft had disappeared down her throat. It was then that I returned the favor. My ass cheeks clamped together as I pinned her head against the small of my belly as I sent rope after rope of cum down her throat. She took it all. As I pulled my cock out her lips tugged on it...fighting to keep my cock meat in her mouth. When I told her it was time to fuck her lips immediately stopped resisting. I lifted her into my arms and held her steady by grabbing her ass cheeks and carried her to the master bedroom. I threw her little 80-pound frame on the bed and quickly mounted her. I pinned her ankles by her ears and without further adieu buried my cock assertively into her soaked pussy. She let out a painful gasp as I unceremoniously broke through her hymen. Soon though her gasps turned to moans of unbridled delight as she experienced the missionary, cowgirl, reverse-cowgirl, standing, spooning, pile driver, reverse-piledriver and finally doggie. It was this last position that Lacy felt a man's seed in her for the first time. Again, my ass cheeks clamped together as my cock convulsed with each rope. She responded with another squirting party. It was a minute of pure orgasmic bliss. Even afterwards for several minutes we each involuntarily met one another at a half way point as we continued to instinctively slow fuck. It was during this time that I eyed her miniature anus with the intention, even by f***e if need be, to sodomize it. I whispered in Lacy's ear not to move and I went to the kitchen to pour some olive oil in a bowl and retrieve a turkey baster and barbeque brush. When I returned, I placed them on the nightstand and pulled some rubber restraints out from under the bed and tied Lacy's wrists to the head board. She submissively accepted her fate. I then got behind her and proceeded to make out with her anus again. This had a relaxing effect on her. That's when I reached for the brush and dipped it in the oil and painted her anus with oil. It glistened in the moonlight and being a quick study, Lacy was making it pucker in anticipation. I then gently and slowly slid my pinky finger in her asshole moving it in and out. Soon it was replaced by my middle finger. Her little o-ring would clasp each finger in a death grip. I was beginning to wonder if this inexperienced, forbidden hole could even accept the purple helmet of my cock let alone an inch or two of my shaft??? I then filled the turkey baster up with oil and gently slid about three inches of it in her ass and then squeezed the bulb releasing a goodly amount of oil into her tight asshole. I then opened the nightstand drawer and pulled out my late wife's egg shaped vibrator, oiled it up and turned it on and inserted it in her pussy. She responded by involuntarily convulsing her ass cheeks again. I quickly oiled up my tumescent cock and pressed it against the spongy exterior of her anus. I whispered in her ear to relax every muscle in her body, which she did. I then pulled my cock away for a brief second to kiss her anus one last time before pressing the head of my cock against that miniature slit and after countless attempts was finally able to break her forbidden seal. She gasped. I told her to relax again and sure enough I was able to slide an inch of my shaft meat in as well. I let out a guttural moan as I could feel the vibrator on the high setting massage the under belly of my cock. Plus, the psychology of sodomizing her virginal, 18-year old ass made that moan so much more primitive. I slow fucked her asshole with just an inch or two of my cock inside her while giving her a much deserved back massage. Soon she was cooing with delight. I took that as a queue to slowly but surly bury my cock in her ass until finally my 8-inch shaft was buried to the hilt. I marveled that this tiny, immature ass could take my adult cock. My ample love sword was simply to large for such an underdeveloped scabbard. Yet, her elastic hole swallowed every last bit of my shaft. I slowly sodomized her for the next half hour while whispering all the raunchy, kinky things I planned on doing to her in the future. Those thoughts however translated into more f***eful thrusts and soon I was fucking her asshole as hard as I fucked her pussy earlier. When I felt my ass cheeks tingle I would pull out to avoid cumming and become hypnotized by her silver dollar sized gape. Then I'd plunge my cock back in for even more aggressive thrusts. Finally, after an hour I filled up my third hole of the night with a creamy, viscous load of cum released from my quivering cock. When I finally pulled out, she started squirting again shooting my loins point blank with her cum. By this time, it was already 2:30 AM. I feared that her parents may be worried, so I quickly dressed her, gave her a long, passionate French kiss and sent her on her way with an extra $100 for her services. That year, Lacy made thousands of extra dollars. To be continued...
Story URL: http://xhamster.com/user/otter3440/posts/139105.html