Freedom is Slavery (10 page)

I moved close to her, feeling the heat of her body next to mine, smelling the sweet scent of her hair. I had fantasized about what it would be like to make love to Julia before—no woman is safe from a man’s imagination—but never thought I would be doing it. I put my hand on her hip, feeling the T-shirt beneath my fingers. I slid it up to reveal the soft flesh beneath. I could feel the waistband of her underwear—white, just like the girl in the spanking video.

I slid my hand into her underwear, cupping her mons and feeling the prickles of hair under my palm. She moaned a bit and leaned back into me. I put my mouth on the side of her neck and kissed for a few seconds before biting her skin. She almost hiccuped with excitement. She pressed her body harder against mine, feeling my hardness behind her ass, I’m sure.

She reached back, grabbing me and pulling me even tighter, pleasuring herself by grinding against my cock. I slid a finger along her slit, finding it wet to the touch. I slid inside of her and she gasped. I bit harder into her neck, like a conquering animal.

She struggled against me, wanting to turn her mouth to mine. Rather than allow that I plunged my fingers deep inside of her, my thumb finding her engorged clitoris. My cock pressing against her in time with my fingers, moving in and out of her. She moved her hand from my back to cover the hand inside of her, pushing me deeper.

"I need you inside of me," she gasped. I allowed her to get up onto her hands and knees and pulled her panties down around her thighs.

As I got ready to push my cock into her she turned her head towards me and said, "You can put it in my bottom, if you want to."

This invitation couldn’t be ignored. I grabbed some lube off the side of my bed and applied it liberally to my cock and her asshole. I pushed myself inside of her, generating a low moan from her that raised in pitch as I pushed deeper. I watched her arm move as she rubbed herself in time with my now-deep thrusts. I could hear her moving towards climax and I knew that I was as well. Her sphincter gripped my cock, pulling me nearer to orgasm.

Her body began to shake and shudder as she pushed her face into a pillow to muffle a scream. I was seconds behind her as I began cumming deep inside of her. My hips bucked involuntarily, plunging me between her cheeks as I dumped my cum into her bowels. She collapsed, sliding my cock out of her as she hit the bed.

I fell next to her, holding her close as we caught our breath. The room was spinning in a combination of drunkenness and sexual revelry. Our chaste friendship was no longer so. I’m not sure if this was as much Julia’s concern at the moment as it was mine.

It turned out not to matter much. We had a few weeks of more sexual experimentation. It turned out that I had quite a hand at spanking and she had quite a mouth for fellatio. However, her employer came between us, making her a terrific offer in another state.

We still talk from time to time. We’re not as close as we were before our sexual adventures and I’m not sure if it’s the sex or geography that got in the way but I don’t think that either of us regret that night of debauchery.

"Your generosity shall be your undoing," read a fortune cookie I opened many years ago.

I don’t often remember the quaint sayings or good advice given after a meal of fine Chinese food but that particular prediction has stuck with me ever since. You see, I like to be generous. I’m inclined to believe in karma so, when I have friends in need, I try to help out however I can.

One way that I have been generous recently was by giving some money to a friend of mine who needed it to move out of her apartment—and away from her psycho roommate. I also gave her a little more money to buy a set of wheels. Essentially, I was helping myself out because she now had a place where we could play or she could drive to meet me somewhere to do the same.

She felt fairly awkward, however, accepting my "charity." She knew that I would never ask for anything in return but wanted to repay me somehow. (I tend to not ask for things I want). Worse, she knew it would be a long time coming before she could cobble together the cash to pay me back.

Inspired by one of her favorite books,
Diary of a Manhattan Call Girl
, she decided to pay me back via sexual favors. Likewise, we had something of a sexual history between us. Taking note from her student loan payment book, she made up a "coupon book" that she presented to me the first time she came over in her new car.

I had only seen her look as provocative as she did in pictures, never in person. She had her hair pulled back, showing off the blonde streaks in her otherwise dark coif. She wore a long, black dress that was cut up to her thigh. She was an absolute knock-out.

Inside of a small folder were twenty pieces of paper. The first one read, "GOOD FOR ONE FUCK"; the second, "ONE FREE ROUND OF CUNNILINGUS"; the third, "YOU DESERVE A BLOWJOB"; and so on. Each had a sexual act on it; some were repeats while others were definitely unique ("ONE FREE HANDJOB FROM YOUR FAVORITE SCHOOLGIRL (GIGGLE)").

I was aroused at the idea of redeeming these but, moreover, I was amused to no end. She really outdid herself. Some had little hand-drawn pictures while others were done up with such elaborate fleur-de-lis and calligraphy that I could barely make out the prurient value.

I tried to put off just how intrigued I was by this. At the same time, my mind was a flurry of activity. Could I only use one at a time? What if I wanted to do multiple things, would I have to use more than one coupon? How long were they good for? What kind of notice did I need to give?

I started to stammer out some of these questions but she put her finger up to my lips and said, "You’ll think better in a few minutes... this first one is on the house." With that, she leaned towards me and put her mouth on my neck, kissing and gently biting me.

I don’t know how she knew it, but that melted me completely. She put her arms around me and gently pushed me down to my knees. She reached down and pulled up her dress to her waist, revealing her lack of underwear. She parted her legs, standing with her feet far apart and pulled my head against her crotch, allowing me to smell and lick her. She knew how much I enjoyed her taste and allowed me to take a long drink from her well.

She pushed me the rest of the way down and indicated with a motion of her hand that I should take off my pants. Laying there, she climbed on top of me—rolling a condom down my engorged cock before sliding herself down onto me, her dress still on. She looked down at me and smiled before moving her hips ever-so-slightly, working herself deeper onto me.

I groaned aloud and she began leaning forward onto her knees, allowing me to slide out before plunging back down and pushing all the way inside of her. Her hands found my buttons and began opening my shirt enough to pinch my nipples. She closed her eyes and leaned her head back as she began riding my cock, twisting and tweaking my nipples all the while.

She began moving faster, her mouth opened and she gave a shaking gasp. She began riding me harder and faster. I couldn’t hold back any longer. I began cumming as I saw her shoulders begin to shake with orgasm. She was merciless, fucking me hard, coaxing the orgasm out of herself. I soon passed my own threshold.

Regaining her breath, and her always cool composure, she pulled a few stray hairs back into place before smirking down at me, standing up, and straightening her dress.

"Now I’ll take your questions," she said, taking out a cigarette and sitting down on my couch.

We worked out all of the pesky details and spent the next six months working through my coupon book. I even managed to earn a few coupons here and there when her car needed some maintenance.

While my generosity might be my undoing someday, this wasn’t the time.

Sometimes a person will do something for me and I’m just amazed at how generous they can be. This happened to me last week when, after months of posting on a web board that I was looking for someone to provide Greek for me, a female friend gave me a call and said, "Have you found your Greek provider yet? If not, well, you could probably talk me into it."

Before I get ahead of myself; when I’m referring to Greek here, that doesn’t mean that I’m looking for a descendant of Greece. Rather, it’s a shorthand parlance for anal sex. Certain things like "Greek" kind of make sense if you think about the historically held notion of philosophers as buggerers.

Likewise with "French" loaning itself to oral sex. Yet, things like "Russian" (rubbing one’s penis between a girl’s boobs) and "Asian" (analingus) just leave me flummoxed.

I don’t know what kind of things trigger a mood or catch a fancy but I had been of the mind that I wanted to bugger a woman again. I hadn’t done it in years and enjoyed it greatly. I’m sure that some would say that doing this is a "power trip" and others would claim that anal sex is only pleasurable to men (either as givers or receivers) but I would counter that I’ve known many women that enjoy receiving anal sex—either due to the implied power exchange or to the actual physical sensations.

Neither of these things seemed to be motivating my friend. Rather, she simply knew that I wanted this, couldn’t find anyone willing, and hoped to fulfill a desire. If that’s not altruism, I don’t know what it.

Fastidious to the point of being slightly obsessive, I was amazed that my friend would allow anything near her anus much less inside of it. The more messages I got from my friend as the week progressed before we met up, the more resolved she seemed. She had started off by saying that I could put a finger inside of her and see how that felt before moving into larger objects. Then the figure changed to a dildo. Finally, she told me that she was able, willing, and ready to take me inside of her.

"This is something I want to try again. It’s been years since I’ve done it and I know that you’ll be nice about it."

She was nervous as heck when I arrived. "Now, how are you going to go about this? Are we going to do it first? Last?"

I assured her that it really wasn’t all that important and that if she was so nervous we could forgo any anal play.

"Oh, no! We’re doing this. I’m set on it. I just want to know if you’re going to do anything first. I want to get ready for it," she assured me.

The logistics were giving her fits. She was so nervous about the anal sex being messy and wanted to be able to jump right into the shower afterwards. I couldn’t help but chuckle.

As it happened, we kissed and cuddled for a while before we stripped and she allowed me between her legs to lick her to climax until she couldn’t take it anymore. Afterwards she moved to the edge of the bed where she bade me to allow her to get me even harder with her mouth. It didn’t take long until she was rolling a condom over my fully-erect member and slicking up the rubber with some lube.

She looked up at me, into my eyes, and I could see that she was still nervous.

I put my hand on her cheek and said, "If you want to not do this, I’ll understand. This isn’t a ‘make or break’ for me. I like doing anything and everything with you."

She stood up, putting her arms over my shoulders, and kissed me deeply. "This is something I have to do. I want to see if I can still do it and I trust that you’ll go slow and will stop if I can’t handle it."

"You have my word," I said before she turned around and got on all fours at the edge of the bed. One of my greatest fears is going into the "wrong hole" when I’m entering a woman so it was interesting to take aim and try to get into this orifice on purpose after so many years. I slid my finger in, first, judging just how much pressure I had to use to open her anus. She moaned and lowered her front half so that her weight went to her shoulders.

I pushed deeper with my finger, sliding in slowly before pulling out. I wasn’t sure how long she was going to allow me access to her ass before she started to feel too self-conscious so I replaced my finger with my cock, aimed at her anus. Using the same amount of pressure, I pushed into her, opening her wider over the head of my cock. She moaned again, breathier this time. I waited, allowing her to get used to the sensation.

Wordlessly, she nodded and I continued; moving deeper inside of her.

It was so unusual, being inside of her bottom. I thought back to the last time that I had done such a thing and that was a mistake. The last time I had anal sex, I had started to worry that I was taking too long to cum, and that going too long would hurt my partner. This planted the seed in my head that the same thing was going to happen again. However, looking down at her, I realized that she would have the courtesy to tell me if she needed or wanted me to stop and that I could fuck her for as long as I needed without having to worry. This put new steam in my stroke as I began doing more than just slowly moving in and out of her and, rather, began to fuck her.

"Oh, yes," she said into the comforter.

Seeing the look of pleasure on her face and feeling her ass tightening around my cock. I put my hands around her waist and began pulling her against me as I pushed into her. I could feel the vibration as she fingered her pussy beneath me, her hand between her legs as I fucked her harder. Unbelievably, she started to cum again and as she reached her orgasm the pressure on my cock triggered my own orgasm. I threw myself into her, over and over again as I exploded inside of her ass.

I slowed and stopped, my cock still spasming as we both caught our breaths.

"Is it okay?" she asked. "Is it all right for you to pull out?" She was concerned about anything that might be on the condom as I pulled out of her.

"Don’t worry. It’ll be fine. I’ll slide out slowly." I did and grabbed a tissue to hide any "evidence" from her. I didn’t want her to feel bad about anything. I disposed of that as she got up.

"It’s okay if we cuddle some more in a few, right? I need to take a shower."

This sounded so much like something that I would say that I had to laugh out loud. "Of course. Do what you need to do to make yourself feel okay and I’ll meet you right here," I said, patting the bed.