tagToys & MasturbationBest Friends Ch. 03

Best Friends Ch. 03

byILuvAnal©

This is the last of the "Best Friends" series. I recommend you read "Best Friends 2" in the TOYS section before reading this story first. If you wish to add "chaining" to your sexual repertoire, I strongly recommend that you research the subject thoroughly before attempting it! Enjoy! – IluvAnal

"Shit!" I swore to myself when the dogs began loudly announcing that someone was coming up the drive.

Four hours previous, I had kissed my wife, Ellen, goodbye as she and some friends were leaving for a four-day golf trip. The minute she left, I stripped and got to work painting the dining room.

I got down from the ladder, put on a pair of jockey shorts and made my way to the living room to see who had arrived. I peeked out through the blinds and saw Sarah, Ellen's best friend, getting ready to ring the doorbell. Ellen had told me that Sarah might drop by to pick up some Yoga tapes. I walked around to the other door and let her in.

"Hey George, did you get any paint on the walls?" She was obviously referring my paint-encrusted torso.

"That's why I paint naked, better than ruining clothes." I was walking to the kitchen and Sarah was following.

"Ellen was going to leave some Yoga videos out for me."

"They're on the kitchen table. She didn't think you'd be by until tomorrow. You want a cup of coffee?"

"Please. I had some errands to run, figured I swing by today. Don't let me stop you from your painting."

"I won't. You know where everything is. Fix yourself a cup and join me in the dining room." With that I left the kitchen, removed the boxers and ascended the ladder. I thought nothing of exposing myself to Sarah, she had seen me naked many times before.

"You're getting there." She said, when she entered the room. "Ellen has been talking about painting this room for a year."

"I figured this was a good day to get it done. As soon as this lousy weather breaks, I'll be spending most of my time in the gardens." I dipped the brush in the paint can and turned my back to Sarah and began painting the border between the wall and ceiling.

"What the hell is that sticking out of your ass!" She asked when she saw the chrome-plated chain link sticking out of me. The rest of the chain, two feet total, was buried deep in my bowel.

"A chain." I answered nonchalantly. Sarah had seen and placed all kinds of objects in my ass. I didn't think this was any big deal.

"A chain? What an ass slut you are!"

"That's me!" I said, proudly, dipping the brush again. "Haven't you ever played with chain before?"

"Can't say as though I have."

"You don't know what you've been missing."

"I can't believe Ellen goes along with it."

"Not in her ass, but she loves it in her vagina. I put it in her and start to play. Just as she starts to come, I pull it out. Sends her right into orbit. When I get this job done, I am going to jack off and when I come, I'll pull it out. It's the best orgasm you can have- alone."

Sarah snickered. "What a pervert you are."

"Don't knock it until you try it."

******

I expected Sarah to finish her coffee and leave, but she was still there long after the cup was dry. We chatted and she told me about her new boyfriend. After the string of losers she has had, this one seemed to be a decent guy that treated her well. I was glad that she finally had the opportunity to be happy, but since he had entered her life, Sarah didn't come over and play with us anymore.

Two hours after she had arrived, I put the last bit of paint on the wall. I stood back and surveyed the room. "What do you think?"

"Looks good. Ellen will be pleased," Sarah said.

"I'm ready for a cocktail. You want anything?" I asked while putting the cover on the paint can and collecting the brushes and rollers for cleaning.

"What do you have?"

"Wine, beer or rum."

"Wine sounds fine."

"Help yourself and pour one for me, too, while I clean this stuff up."

Sarah grabbed a bottle out of the closet and poured a couple of glasses. I was cleaning the brushes at the sink. She walked up behind be and gave the chain in my ass a playful tug.

I stiffened- for two reasons. First, it took a great deal of effort to keep the chain in place, I was afraid that any manipulation would cause a "chain reaction" and it would fall out before I was ready. The other thing was that I was certain that Ellen would be upset (no, down right pissed) if she knew that Sarah was playing with my ass while she was absent.

"I hope Gary likes ass play as much as you."

"You don't know?"

"I haven't let him screw me yet. And I don't want to scar him away. But, I'm so horny I'm about ready to crawl out of my skin. Seeing that chain sticking out of your ass hasn't helped either. I still can't believe Ellen goes along with you. I've known her for twenty years and I didn't think she had a kinky bone in her body."

"I hate to tell you how long we had that strap-on before she would use it on me. Now, she loves it. It was the same with the chain."

Sarah drained the last few drops of wine from her glass. "Mind if I have another?"

"Help yourself."

She poured another glass, then out of the blue asked, "So, when were you planning to jerk off?"

"Whenever. I was going to reward myself for finishing the painting." I poured another glass for myself.

"Well, the painting's done." The implication of her sentence was obvious.

"You want to watch?" I knew the answer.

"Isn't more fun to have somebody else pull it out?" Well, I thought I knew the answer. She didn't want to just watch, but she wanted to participate.

"I don't think Ellen would approve. Do you?"

"Probably not." Sarah replied sadly. "But, I won't tell if you don't."

We sat and drank in silence for a few minutes. The conversation had given me a raging hard-on and the testosterone and wine began to impair my judgment. "Why not." I finally said.

Sarah's blue eyes brightened.

We went into the living room, I laid down upon a towel and raised my knees so that Sarah had access to the exposed end of the chain. She took a seat between my legs.

"Ok, now how do we do this?" She asked.

I took my pole in my fist and slowly began to stroke. "When I say 'Now', you pull the chain. Pull it all out in one motion." With that, I closed my eyes and began to concentrate on what I was doing.

As the pending orgasm began to build in my balls and prostate, I increased the pumping of my prick. I felt something touch the sensitive head of my dick, but I was too close to release to investigate. My hand was moving faster and I soon felt the unmistakable touch of a tongue on my shaft and soon my hand was bumping into a pair of lips that were working my shaft in unison with my hand.

"Now!" I yelled, as the first of my semen began coursing it's way to the outside.

On command, Sarah pulled the length of chain out of my anus. My sphincter clamped down on each emerging link. Stream after stream of my cum erupted from my cock and into the woman's mouth. My hips bounced uncontrollably, forcing my cock deeper and deeper down her throat. By the time the effects of the orgasm had worn off, Sarah had masterfully gleaned every drop of semen from my shaft.

A few moments later, the full realization of what had just transpired came to me. We had definitely crossed the line.

As if reading my mind, Sarah looked at me. "I'm sorry. I just couldn't resist." There was nothing more to say. What was done, was done.

"It felt wonderful." I said, finally. "Thank you."

Sarah held up the slippery chain that she had pulled out of my ass. "I can't believe you have all of this in there."

"The one I use on Ellen is twice that long." I failed to mention that two feet of it was all I could ever fit in her.

"Really!" She said. "I've got to go to the bathroom." She got up and went upstairs.

I got up, poured another glass of wine and began to pick up the drop cloth from the dining room floor, all the while, trying to shake the pang of guilt I felt.

In the amount of time Sarah had been in the bathroom, I had managed to remove all of the protective masking tape from the woodwork, picked up the drop cloths and had taken the ladder out to the garage. When I got back into the house, Sarah was standing in the dining room, stark naked, holding the four foot length of chain, the tube of KY Jelly and an empty enema bottle. She had gotten into our "toy" chest.

I stood speechless at the sight. For a woman that had just turned fifty, she still looked mighty fine. Noticeably absent from the last time I had seen her naked, was the large, hairy bush that once covered her pubis.

She was the one to break the silence. "I know what you are thinking, but I'm horny and this may be the last time you get a chance to teach me the chain trick." She was right about that. If Ellen found out about this, it would be last time I would have a chance to breathe!

"What the hell. You know what will happen if Ellen ever finds out about this?"

"Believe me, I know! But, I am certainly not going to be the one to tell her."

I nodded. "Very well. Go into the living room. I'll be there in a minute." I took the empty enema bottle from her to throw in the trash. "I take it you want the works."

Sarah smiled. She had a lustful look in her eyes.

I went into the kitchen and got everything I would need- a towel, a large, plastic garbage bag and a bowl. Sarah was lying on the carpeted floor on her back.

"Pick up your butt." I ordered. When she complied I laid the bag on the floor and covered it with the towel.

"Why the plastic?" She asked.

"You'll see." I said making the rest of the preparations.

The secret to making "chaining" a pleasurable experience is making certain that there are no sharp mill marks and using plenty of lube. I took the chain, placed it in the bowl and squeezed half a tube of the KY on it. I then "stirred" the mixture until a thick layer of lubricant covered every inch of the chain.

"Are you ready?" I asked. Sarah nodded. "OK, roll over and stick your ass in the air."

When Sarah was situated, I stuck a finger in the bowl and covered it with a generous amount of the jelly. I then slowly inserted the finger into the woman's tight pucker. Her body resisted, at first, but my finger soon found it's way in- enticing a moan of pleasure. When my finger was able to move about freely, I placed another finger in along side and buried both to their full length. Within a few moments, I was aggressively screwing Sarah's ass with the two fingers-much to her delight.

I withdrew the fingers grabbed one end of the chain and inserted the first 1/4-inch thick link. Inserting chain into either the anus or vagina needs to be done very carefully to prevent pinching. I compressed the second link into the first and pushed it in. The process was continued, link by link, until I had a foot of chain inserted Sarah's greedy ass. In the position she was in, the weight of the chain kept it straight, so that it tickled the sides of the colon for it's entire length. When you insert the chain while lying on your back, on the other hand, it has a tendency to "ball up" (my preference as it puts pressure on the prostate).

I allowed Sarah to get used to the feeling, gave her three hard, open-handed spanks that elicited a screech of surprise and pleasure. I instructed her to roll over. Without the cover of hair, her bald pussy showed its arousal. Her vaginal lips were a bright pink, fully engorged and very wet. I dipped a couple of fingers in the bowl and inserted them into her wet snatch. Sarah bucked her hips to meet the invaders. I twisted my hand and rubbed my fingertips along the roof of her vagina until they found the little nubs that denoted her G-spot and gently stroked the spot. This was more for future reference than arousal. Based on her reaction, it probably would have taken only a few moments of this stimulation to send her over the edge, but for the moment, that was not my goal.

Once I was confident that I could instantly relocate her spot when the need arose, I made certain that she was well lubricated, took the other end of the chain and repeated the slow, careful process of inserting the chain- link, by slimy, silvery link past her swollen, glistening lips.

I know that the old axiom "Tiny woman, cunt as big as a bucket" doesn't hold true for all tiny woman, but it certainly applied to Sarah. When we watched the video of her and I sharing a cucumber, I was amazed at the ease with which she had impaled herself the enormous vegetable. So when I had crammed the first two feet of chain (Ellen's limit) in her vagina, I was not surprised when she rocked her hips back and the ball of chain rolled further back into her abyss, giving me room for the last remaining foot.

I studied the scene before me for a few moments. Here was a tiny, naked woman laid out on her back, knees up, her cunt full of almost three pounds of metal, a stretch of chain connecting the ball in her pussy and the other foot of chain in her ass. It was a heavenly sight and my recently drained cock was taking notice and coming back to life.

"How's that feel?" I asked.

"Wonderful," Sarah mewed. She was rubbing her right breast and pinching her nipple.

"Whenever you are ready, you can begin rubbing your clit." The words had no more escaped my lips, when her finger went to work.

"Easy, not too fast." I coached. I was watching for all of the signals that would tell me when to make my move.

She was gently rocking her pelvis, enjoying the feeling of the weight rolling around in her cunt. Her eyes were closed, and she began to increase the rhythm of her finger on her clitoris. As soon as I saw the muscles in her thigh tighten, I plunged my finger along side the chain and put the fingertip directly on her G-spot and applied pressure. My other hand grabbed the section of chain that connected the buried ends.

As soon as the first orgasmic contraction began, I pulled my finger from her G-spot, held the chain at her anus and pulled with a fluid motion, making sure that the end of chain in her ass emerged at the same time as the other end came out of her gaping snatch.

The impact of the move was instant. Her entire body tensed and heaved, an un-human scream came from her mouth (it's origin was from the very depths the chain just occupied), the walls of her vagina contracted with enough force to eject it's contents of KY and natural fluids all over her legs and my chest. Then she lost bladder control sending a forceful stream of urine all over both of us and the towel. We were a mess.

I sat between her legs and marveled at the enormity of her orgasm as it slowed from its violent beginning to more the subtle muscle twitches that gave the appearance that she was shivering. The sight, smell and sound had an arousing effect on me. I noticed my raging hard-on and the puddle of pre-cum that was growing under it. Sarah was already a mess, so I decided to add to it. I raised myself onto my knees and aiming my dick at her bald mound, began masturbating. It didn't take long before I was adding my own fluids to hers, but she never noticed. When I was done, I took the palm of my hand and mixed my semen with her vaginal fluids and urine, smearing it all over her mound, belly and legs. I took my thumb and gave her clit a couple of gentle flicks, causing her to scream and squirt again.

I got up, went to the bathroom and got a wet wash cloth to clean Sarah up a bit. Previous experience with a perfectly executed "chaining" told me that she wasn't going to be moving for a while.

I wiped her up the best I could, replaced the wet towel under her with a dry one, covered her still quivering mass with a blanket and went to the shower.

"Are you alright?" Sarah hadn't moved in the ten minutes it took for me to clean up.

Her eyes fluttered open. "I'm still coming." She replied blissfully.

I smiled and gave her a kiss on the cheek and let her drift back to Nirvana. It was getting late and I was getting hungry, so I decided to cut up veggies and cheese for an omelet, but I would wait to cook it until she was up and about.

******

Sarah had been sleeping off her orgasm for nearly an hour. I was about to go try to wake her when I heard her pad into the kitchen wrapped in the blanket.

"How are you feeling?"

"Wonderful! I think I am still coming." She said groggily. "If I had known about that trick thirty years ago, I would have never gotten married."

"I'm going to cook up an omelet. Why don't you go take a shower and we'll eat."

"No thanks. I think I'll get dressed and go home. That towel was still dry."

"Different towel." I went and retrieved the sodden towel from the laundry and showed it to her."

"All that came out of me?" She said, surprised.

"Ellen always squirts when we do that, but never like you did. You pissed all over me, too!" I left out the fact that I added a little to the mix.

"You should have video taped it, because I don't remember a thing." Sarah turned and left the kitchen. I went about cooking my dinner. I was eating when she finished dressing, thanked me and left. It wasn't until I was cleaning up the dishes, that I realized that she had forgotten the Yoga videos.

I was getting ready for bed, when the phone rang.

"I totally forgot about the videos," It was Sarah.

"They're still on the table, come get them whenever you want." I replied.

"Can I get that chain at any hardware store?" I smiled at her question.

"Yes. But if you like, I'll pick up a section for you and clean it up. I have to go to the store tomorrow anyway. Five feet will cost you about ten bucks."

"If you don't mind. Susan's car is in the shop, so I have to pick her up after work tomorrow afternoon. We'll swing by around six. If that's OK with you?"

Susan is Sarah's twenty-four year old daughter. I smiled. "I'll be home by 4:30, so, any time."

"Good night."

As soon as I hung up the phone, I dug out the video camera and plugged the battery charger in. I missed one opportunity for a good video. I wasn't going to miss another. It looked like Ellen wasn't the only one that would be hitting the "links" tomorrow.

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