Chapter Text
Nine Holes - Boxed Set
Story_codes: MF, Mf(14), Mg(11), oral, anal, cons, spanking
Nine Holes - Boxed Set
Written by Bemused
Copyright (c) 2003, Bemused.
Chapter 1
I stepped out of the shower and was toweling my hair when Jessica walked in. Jessica is the fourteen-year-old daughter of Vanessa, the owner of the house in which bathroom I was standing. Jessica was dressed only in a spaghetti strap T-shirt that didn't come down far enough to cover her bellybutton and a pair of skimpy white panties. She smiled at me shyly and lowered her gaze to stare directly at my rising cock.
It was a Saturday afternoon and Jessica and I were alone in the house. I had just returned from playing golf at the nearby country club. Her mom was at the dress shop she owned and her ten-year-old sister, Allison, was staying at a friend's house this weekend.
Jessica was a good-looking young lady with short brown hair and a fairly cute face. In most families she would have been the "pretty" daughter. Compared to her mom and gorgeous younger sister, though, Jessica was the plain Jane of the family and it showed in her self-confidence. The lack of self-confidence made her look less attractive than she really was.
I had noticed the fourteen-year-old's interest in me during the week or so I had been staying with her mom. She would always find excuses to be wherever I was and would stare at me whenever we were in the same room. I was used to women and girls staring at me. It was my good looks that kept me living in beautiful homes like this and driving my nice car and wearing nice clothes.
I had an apartment above the garage at my brother's place but spent most of my time staying with female clients. I am a personal trainer and specialize in setting up and managing personal fitness plans for wealthy women. My services often include satisfying the peaking sexual urges of my clients and I was born for the job. I am in my late twenties and in extremely good shape with the kind of body women crave. But more importantly, I have a nice thick 7-inch cock and it can stay hard forever. Three orgasms in an hour and six or seven in one day are not unusual for me. Along with my natural abilities, I have developed some sexual skills that keep me in high demand among a grateful circle of wealthy women.
All the women I sleep with, and there are many, are aware of the limits of my relationships with them. Many are still willing to share their house with me or shower me with "presents" even though they know I am probably screwing other women at the same time. After all, I was usually screwing them while I was living with some other woman. I have only three rules for living with my clients. Rule number one - Never use the "L" word. Two - Never bring another woman to the woman's home (unless she wants me too). Three - Never stay more than one month at a time with any woman lest they start to get feeling domestic.
Daughters and maids didn't count as cheating in my opinion since I wasn't the one who brought them into the house. I had on several occasions been screwing the mom, daughter, and one of the hired help in the same house at the same time. Golf being my second favorite thing after sex, I tended to score my sex life the same way. To date my personal records included five different holes (orifices) in one day, seven different holes for a single house, and the record for related females (two sisters) was five holes.
Jessica was a little younger than usual for me, but she was obviously interested and I wasn't going to disappoint her. She was a nice kid and, based on how she was dressed when she walked into the bathroom, had intentions on seducing me.
Whatever she had intended to say or do to seduce me when she planned this little bathroom scene was gone. Jessica couldn't take her eyes off my cock. I knew she had not had any serious boyfriends to date since her mother frequently commented on her oldest daughter's shyness around boys her own age. Mom had even said out loud in front of Jessica that she was worried Jessica might be gay. Jessica certainly wasn't being shy or acting like someone with lesbian tendencies today.
I finished toweling my hair and threw the towel on the floor. I walked directly to Jessica and, taking her chin in my hands, tilted her face up. I looked into her eyes and leaned down and kissed her.
She was tentative at first, but soon figured out what she needed to do. I slid my hands from her face down her neck and shoulders to her firm young tits, which were covered only by her thin cotton shirt. I caressed her breasts and she began to moan and press her body against mine. She ran her hands over the hard muscles of my chest and stomach.
Her reaction to my kiss and caresses was all the encouragement I needed. I slid my hands down to her ass and picked her up. She slid her legs around me and I lowered by panty-covered pussy so it rested on my iron hard erection. I easily carried her 90 or so pounds into the master bedroom and sat her on the bed. The bed was unmade and still messed up from Jessica's mom and I screwing last night and this morning.
I pulled Jessica's T-shirt over her head and sucked her pebble-sized nipples into my mouth. As I was giving her firm apple sized breasts my oral attention, I pushed her onto her back and slid may hand down into her panties. Her pussy was lightly covered with pubic hair and soaking wet. I was able to slip my finger along her slit and into her tight pussy without any problem. She had no cherry. I lifted my mouth from her breast and spoke for the first time since she walked into the bathroom.
"Jessica, have you ever had sex before?" I asked.
Jessica shook her head no. I believed her based on what her mom had told me about her limited exposure to men and boys. She must have broken her hymen masturbating, riding a horse, or something.
I kissed her again and alternated my lips and tongue between her face and her tits. Her skin was flushed and she was breathing rapidly from the minimal foreplay I was giving her.
I continued to slide my finger in and out of her pussy and used my other hand to slide her panties down her slim legs. She helped my by pulling her legs up and out of the panties, kicking them off and spreading her legs. She may not have fucked before but she certainly knew what she wanted.
This young lady was so worked up I didn't bother with any more preliminaries. I climbed between her legs and pressed the head of my cock against her wet virgin pussy. I slowly pushed into her until the head and an inch or so of the shaft of my cock was inside. I then began to move back and forward, pushing in slightly farther with each stroke. After about five strokes I was fully inside her and I stopped to enjoy the feeling. She was so tight it was almost painful.
Jessica wasn't my first virgin pussy but she was certainly the tightest. Tighter even than some of the virgin asses I had enjoyed on my more adventurous female clients, including Jessica's mother just two days earlier.
After a few moments to allow my balls to cool down and Jessica's pussy to adjust, I began to slowly fuck the young girl. Jessica still had not said a word since entering the bathroom. She was soon making plenty of noise though. She began mewling and keening louder and louder. It was a good thing we were home alone. Anybody in the house would have known what was going on in the master bedroom. I was surprised at how vocal she was since her mom was the silent and reserved type during sex.
Jessica began to orgasm as I was starting to pick up speed. She wrapped her arms around my neck and jammed her pelvis up at mine. The nymphet's hot action and spasming pussy caused me to shoot my first load sooner than I had planned. I usually have pretty good ball control and can hold back my orgasms at will. But this super tight pussy and firm young body was too much. I wasn't worried about coming inside her. I had been fixed and was shooting blanks. Knocking up one of my clients, let alone one of my client's daughters was not good business.
I paused only long enough to recover from my powerful orgasm and resumed fucking this little teen fuck toy. Jessica seemed surprised at first, probably having heard that once a man came it was all over. She soon got into it though and had two more orgasms before I was ready to blow my second load.
When I was getting close, I raised myself off her and pumped into her hard. As I felt the cum rising in my shaft I pulled out and rose onto my knees. I reached down to jack myself with one hand and, reaching behind her head, pulled Jessica to a sitting position with my cock inches from her face. She reached out on her own and grabbed my cock, jacking it as I had been.
The first spurt landed on her hair and the rest landed on her face and chest. She continued to pump my dick with her hand until I was done shooting. Again my cock stayed hard. I sometimes lost my full hardness after my second orgasm, but not today.
She looked at me with her jism-covered face and spoke for the first time.
"Doesn't it get soft Ty?" she asked innocently.
"Not with a beautiful young lady like you." I replied gallantly.
Jessica, used to her mom and sister getting the compliments, basked in the attention.
I pulled her face to my cock, and with only a glance at me to make sure she understood what I wanted, she slid my cock into her mouth. Her lack of skill was obvious, but her eagerness to please more than made up for it. I was especially impressed that she did not object to the taste of my cock which was coated with the mixture of her juices and my ejaculate.
Every couple of minutes, Jessica had to pull her mouth off my cock. While her mouth, unused to having a thick cock stretching it, rested, I wiped the cum from her face and chest with my finger and fed it to her. She sucked my finger clean each time. As soon as she could though, she would put as much of my cock as would fit into her mouth and suck like there was never going to be anymore cock in her whole life. If she kept up like this though, I was sure she would have all the cock she wanted.
She was soon, with a little direction from me, sucking cock as well as her mom ever had. I let her suck and lick until her mouth got too tired and then pulled back. I then reached into the dresser drawer and removed some lubricant and a vibrator her mom kept there.
I rolled Jessica onto her hands and knees and adjusted her legs to present her ass at the right height. Her small butt cheeks were parted sufficiently for me to see my next target. Her asshole was pink and clenched tightly closed. Jessica looked over shoulder at me curiously. I didn't know if in her sex education she had learned about anal sex, but I was going to teach her everything she need to know.
I opened the lube and squirted a large glob onto the crack of her ass. I then used my finger to spread the lube onto her anal pucker, massaging the tight ring of muscle. Jessica froze at the unexpected contact and began to pull away. I grabbed her hip with my other hand and held her in place. Her ass was instinctively wiggling and trying to evade my fingertip.
Jessica finally got the message about what I wanted and held her ass still. I instructed her to relax and began to probe at the center of the tight pink hole. With a little practice she gradually was able to relax the knot sufficiently for me to press my finger in her ass to the first knuckle. I slowly worked my finger into her ass just as I had my cock into her pussy, pulling out a little and then pushing in a little farther each time.
Once I had my finger buried almost to the palm, I released Jessica's hip and grabbed the vibrator. I turned it on and placed the buzzing instrument against Jessica's wet pussy from behind. Jessica jumped at the initial contact of the cold plastic but was soon pressing her ass back seeking contact of the vibrator against her clit.
I used her own rocking motion to fuck my finger in and out of her ass. The distraction of the vibrator allowed her to relax her rectal muscles and my finger was soon sliding relatively easily in and out of her butt hole.
As I saw her orgasm approaching, I placed the vibrator in her hand and directed her to use the vibrator on herself. I then lubed my cock and began to rub the head of my cock up and down her butt crack, being sure to press extra firmly against her well-lubed pucker.
When her orgasm hit and she was hunching her hips against her new plastic friend, I placed the head of my cock against her asshole and pushed firmly in. She squealed in the most delightful manner but didn't even try to pull away. I was able to push three inches of my cock into her virgin ass on the first stroke and began to butt fuck her with shallow strokes while she was still in the midst of her orgasm.
By the time she was done cuming and had dropped the vibrator to the bed, I had four or five inches up her ass and was doing some serious in and out action on her so recently virgin ass. If I was a world champ at anything sexual, it was busting a cherry ass.
Jessica looked back at me with wide eyes. I smiled at her and told her how sexy she looked with my cock in her ass. She took a few moments to 'assess' what was happening to her, apparently decided that it was all right and began to get into it.
I started pulling her hips back as I pushed in and after a couple of tries she got into the rhythm. My prick was soon buried balls deep in her ass and she was slapping her butt cheeks into my stomach on each stroke.
After two orgasms in the past twenty minutes, even I took a little while to reach the third. Her super tight ass was just the thing to work me up to my third load in record time though.
After I shot my load in her ass, my cock finally started to soften and her back and forth motion slowly worked my shaft out of her ass. When the head popped out, I saw that her formerly tiny pucker gaped slightly. It stayed open for a few seconds and then slowly closed. She held her kneeling position until I pulled her up to me for a kiss.
In the time before her mom was to return Jessica and I got a shower together and I spent some time complimenting her body and sexual prowess. She positively glowed at the praise and even in her post sexual stupor was as animated as I had ever seen her.
After we were clean and I had put away any incriminating evidence we still had time for a little more action. I taught her how good it felt for a female to have her pussy eaten by an expert and then just as her mom was pulling in the driveway, blew a load of cum in her mouth.
We had to scramble a bit to get decent and presentable before Vanessa walked through the door. It was worth it though. I had managed to break in all three of her cherry holes in less than two hours, a new personal best.
I had high expectations of many more such afternoons in the next few weeks. And possibly even setting some more personal records. The most "holes" I had fucked in one day was five. Between Vanessa's experienced mouth and pussy, and her recently christened asshole and her 14-year-old daughter Jessica's newly broken in holes, it was entirely possible that I would get to play six holes in one day. That would also break my related women record of five.