Friend with Benefits

I Opening Myself to Possibilities

I reached with all my strength until I could just, ever so swiftly, clip the end of the final handcuff around the thick upright post of the bedframe. It clicked as my body recoiled and I found myself in that sweet, blissful state of full spread-eagle bondage. It had taken me an hour to put myself into my predicament, most of the day to prepare, and about four years to work up the courage to do this. I’d know if it would work within the hour.

My friend was a very attractive woman, lithe, thin, and with auburn hair that reached almost to her very tight ass. When I first met her, we were walking home from the bus together. Of course I’d seen her before, but never had a chance to strike up a conversation. On the day we met, I couldn’t help compliment her on her outfit -- charcoal suit and narrow skirt with a slit that went up under the jacket; shiny black high-heel boots that came to just below the knees; and a bright white blouse with a plunging neckline that showed off a perfect neck, deeply tanned and freckled, and bordered by excellent cleavage. But good as she looked, my initial intent was to simply meet someone from the neighborhood. My work hours gave me very little chance to meet people. Her name was Billie Ashe.

A few days later my wife, April, and I invited our new acquaintance over for Sunday lunch. We very quickly became good friends, because there were things that April and Billie liked to do together, things that Billie and I liked to do together, and things we all liked to do together. However, we did not share the information that April and I had an open marriage, in part because it was not our intent to seduce Billie, and in part because April’s sexual energy had been pretty low for the past several months. She’d been in an accident and had knee surgery, and the prescribed pain killers had kinda whacked her sex drive.

As April recovered, our sex life picked up a bit and she’d sometimes spend time with her “boy toy,” as she called him. But I’d been on such a low diet of sex for so long that my interest had remained minor. That is, until one day when April, Billie, and I went over to the local pool.

It had been a very hot August day, the kind people on TV were calling “sweltering,” and the three of us had decided to try cooling off in the apartment’s pool. I guess it really was hot, because we got there just about twilight and there was no one else there. Understandable, too, because it was so much easier to sit in front on an air conditioner and have some ice cold drinks at home. The privacy the three of us were able to share was most welcome. For one thing, I’d never seen Billie in her swim suit before, and it was quite a treat to see! I’m not sure what it was made out of, but it was like spandex or a one-piece lady’s Speedo, very sheer and damned near see-through. It rode high over her thighs on each side, and her nice belly muscles were clearly outlined. But what help me rapt all night was the sight of her tits! Oh My God!!

Let me first explain that April is hot, and always has been. She’s got the kind of body that men fantasize about, with great legs, an hour-glass figure, and a rack that says “trophy” in any language. Her boobs are magnificent globes that produce a Grand Canyon of cleavage. Her nipples are perfectly formed, a bit larger in area than my thumbprints, and stand erect at any hint of a chill or breeze. I can honestly say that I still get an erection every time I see her peel out of her bra after work.

Billie, however, was the total female opposite. She is thin, like a model, and her frame is lean and taut -- there’s no sign of flab or extra muscle. Her belly isn’t smooth, it’s an understated but evident six-pack. She hasn’t got much of a waist, but she looks very girl-ish. And though Billie’s chest isn’t really a rack, she has fantastic boobs. April has globes, but Billie has hemispheres, each tit about the size and shape of one half a perfect smooth cantaloupe melon. Because they are small, they have very little weight, and so they stick straight out. Because Billie loves plunging necklines, I always get the impression that her chest is advertising. “Hey, look at us!” Hey, I always do. And another difference is Billie’s nipples. April’s are slightly oval, and when not erect lay absolutely smooth. Billie’s though, are perfectly round, nearly twice the area of my thumbprint, and are formed of permanently puffy areolas. Even when her nipples aren’t erect, they LOOK erect through sheer fabrics. And when they ARE erect, they are huge! They stiffen into a pair of, well, thimbles. Billie’s nipples get erect whenever she is even slightly cool. I saw them pop up once on a warm evening while we were watching a TV show that had a snow scene. Great as her nipples are, they embarrass Billie, who usually has them covered by petite but padded bras.

Well, that night at the pool was too much for me, and I was having my own problems with something getting erect. Worse, my long “dry spell” had made me a bit careless in choosing my own swimsuit, which was a Speedo barely more than a thong. When the women got out of the pool, I was too embarrassed to join them. I’d never so much as said the word “sex” in Billie’s presence before, so I didn’t want to have her see my boner now! April saw it, tossed a towel to me by the side of the pool and when we finally got home she pushed me on the bed, yanked down my Speedo, and gave me a jerk-off I’ll never forget.

And then, about a month later, just before falling asleep, April asked me a question: “Have you ever wanted to fuck Billie?” Not that April had a problem with it, but I did. Yes, no, maybe? Yes, I’d like to ride her like a Harley; no, I didn’t want to risk what had become a wonderful friendship for us all; and maybe, because whenever I though of Billie from that moment on, all I could do is imagine her naked. The fact that Billie had had poor luck with men, and had recently confided to April that she hadn’t had sex in four or five years, made it even harder to put the idea of fucking her out of my mind.

Several months later, April had scheduled to prolong a business trip, taking her “boy toy” along for an extra four days of wild and crazy sex. Billie, friend that she was, asked me to come stay with her, where we’d watch late movies and just hang out the way good friends do. April left town on a Thursday afternoon, and the next day I went to stay with Billie.

Billie got home from work about 6:45 Friday evening, and we made a quick barbeque to cook up some burgers for dinner. Even in the shade away from the barbeque, it was about 96 degrees. While I watched the fire, Billie went to change, and when she came back I almost dropped my jaw. She had put on the skimpiest pair of denim shorts I’d ever seen up close, and her top was a red-and-white checkered shirt that she’d drawn up and tied into a very narrow halter. Fortunately, the burgers were done, so between the commotion of moving things to the table and my trying to hide it, Billie probably did not see the beginnings of my erection. I was momentarily glad to be wearing my jeans and not that Speedo.

Anyway, dinner went well. Then we went to hang out in front of the TV. To save on the electric bill, Billie kept the air conditioner off, but two small window fans provided a cross breeze. We were both covered in sweat, and my own nipples were extremely erect. Billie had ditched her bra when she had changed, so I could see her stiff nipples, too. Any time I looked her way, I’d uncontrollably stare down her cleavage, or stare at the nipples under her shirt, or stare at her sleek, shining belly, or...

Billie had to work on Saturday, but would be home around 4. She rose and left without making any noise, so I continued to sleep on the living room couch. When I did awake at 9:30, it was because I stabbed myself in the gut with a huge erection. I wasn’t wearing anything, so when I stood up, my prick jutted straight out in front of me, bouncing as I walked. I went to the small kitchen, poured a coffee, and had it with some toast. I was still fully erect. Then I went to the shower, first hot, then cold. Still erect. Tried to jerk off, but couldn’t; I’d been hard all night, apparently, so I was too sensitive to reach orgasm.

I dressed, did some dishes, vacuumed, anything to distract me. By noon I had done a lot, but I was also still erect. I sat down on the back patio and stared at the trees beyond. In my mind, I heard April’s question: “Have you ever wanted to fuck Billie?”

Yes! Okay? Yes, goddam it, I wanted to fuck her. I wanted to mount her and ride her non-stop for a week. Then I wanted her to ride me for a week! Silly question! Of COURSE I wanted to fuck her!

And then I prepared to make it so.

I drove to the “adult” store a few miles away and bought everything I needed. I got home, made a few modifications, and began my plan. It was shortly after 2, so I had about two hours to get ready and make this work.

Or lose a wonderful friend.

First, I carefully wrote out a letter to Billie, put it in an envelope, and suspended it by some thread just inside the front door. It would be dangling in her face as soon as she walked in. On the envelope I wrote:

READ ME RIGHT AWAY! IMPORTANT!!

Next I had to do something that would signify a major sexual violation. I wanted Billie to get a bit angry, but also determined to do something about it. So, I broke all my rules and went rummaging through her drawers and closet, and found... a nice variety of sex toys! Rubber dildoes, battery-operated dildoes, electric dildoes, a double dildo (one for cunt, one for ass), a rubbery bra with soft knobby fingers inside, a leather bra with nipple holes cut out... Maybe Billie hadn’t had sex with a man in five years, but she had certainly been diddling her clit! I spread her toys all over her bedroom, all in conspicuous view, and made sure the electric toys were plugged in.

Billie has a very large bed. It’s queen-sized, with an extra thick mattress, all within a very sturdy iron frame. There was no question about using her bed. To get maximum effect I had to violate her space.

I snapped locking cuffs on each of my ankles, and, wrapping the other ends just right, attached the far ends to the two posts at the foot of the bed. My legs were spread extremely far apart, in fact enough so it was just the least bit uncomfortable. Fine. That meant that when I lie down, they’d be at maximum spread and I’d have no give for wiggle room.

When I got home I put the hand and ankle cuff key on a length of thin, strong chain, and welded the ends together. This formed a chain loop that, as I measured, was the exact circumference of my balls plus erection. What I needed to do was put the chain over my resting, limp penis, and then pull it over each testicle and gently massage it to the very base of my genitals. I needed to be quick because, first, fiddling with my crotch began the erection process, and second, being so spread open already also began the erection process. Note to self: Next time, put chain collar around genitals FIRST.

An hour to go.

I was erect and hard, but I could become a bit longer and much stiffer as I fell into self-bondage. I attached the soft cuffs of the wrist restraints on each wrist and reached up and easily attached the first to one of the headboard’s posts. The second required some persistent stretching and several attempts, but when I heard that handcuff “click” around the four-inches of iron, my body just went limp. I was pried open in every good way, and I was loving it. As planned, I could not pull an ankle or hand a single inch closer to my body. My groin was 100% vulnerable to whatever Billie might choose to do, and I was ready for anything she’d dish out.

I loved being ridden. I love being ridden past orgasm. I love being milked, forced to have orgasm after orgasm. I love orgasm denial, being teased but left stiff for hours on end. I’ve had my erection paddled with a ping-pong paddle, fly-swatter, and a riding crop, and stayed hard but got hornier. I’ve had my balls coated in Ben Gay and my prick tip tickled with rabbit fur and was in fuck heaven.

This time, though, I had put myself into bondage, and in a way very carefully planned to be inescapable BY myself. I’d only brought one key into the apartment, having dropped the duplicates off at my place on the way back from the store. That one key was on a chain wrapped around my genitals, and that chain no longer had a clasp. It was welded into an unbroken chain. It fit tightly -- not just perfectly, but snugly -- around my cock and balls, and could now only be removed when I lost my erection. Until the chain could be removed, the key could not be retrieved and my cuffs could not be unlocked. Until then, that tiny key would dangle uselessly just outside my asshole. Which was also spread wide and vulnerable. Billie would have to come home and, one way or another, do me.

It was hot, and I was glistening in sweat. I heard something outside. It was 3:40 and Billie’s voice was carrying, something about swimming. A second voice replied to hers. It was a female voice. I heard Billie’s key in the lock and the door opened.

“What’s this?” Billie said, as the envelope dangled in her face. And then, “Oh, go ahead in there to get changed...”

Billie was home. She was not alone, but with another woman. And she’d just told that woman to go get changed in the bedroom where I was naked, bound, helpless, and just dying to get raped!

And then, with my heart pounding so hard I thought it could be heard outside, there was a hand on the bedroom’s door knob, and it wasn’t Billie’s!

10.02.13