High-Low

"Now for the rest of your challenge. I want you to swallow this completely," I pointed to my boner that was now in a perpetual state of arousal, "but you can't make me cum. If you can't get me all the way down your throat, or if I cum before you finish trying, you lose and have to sit out a round."

Annie looked more closely at the object of her challenge. My cock was at its full seven inches and curved slightly toward my stomach. "Lie down," she directed. I lay back as she straddled my head. She handed me the little pocket rocket. "If you want to keep yourself occupied, this may help," she offered. I knew she wanted my mind to be on something other than her lips on my cock, but I didn't have a problem with that.

As she knelt over me in the classic 69 position, I reached up to spread her pussy lips with one hand and turned on the little toy with the other. I felt her mouth descend on my rod as I moved the vibrating white tool through her folds and forward to touch her hooded clit. Her mouth was open as wide as possible to avoid stimulating my cock. I heard Lisa and Kia in the background softly chanting, "Go Annie, Go; Go, Annie, Go." She seemed to be making good progress despite my manipulation of her clit, which now was fully out of its hood and enjoying the vibrations of the pocket rocket. At one point, she gagged and quickly lifted off to cough and catch her breath, but then dropped back down to continue.

Even though I was keeping myself busy working on Annie's pussy, I couldn't ignore the feeling of her throat as it encircled first the crown and then the sensitive skin at the top of my shaft. Annie was trying to keep her oral movements to a minimum, but each was magnified by the super sensitivity of my organ at that point. I increased my attention on Annie's pussy and was rewarded with first one, then a second, drip of nectar. I used my finger to wipe away the liquid, and then sucked it off with a loud smack.

Finally I felt her lips nestle into my pubic hair. I was now buried fully in her throat while Lisa and Kia cheered their co-worker. Annie carefully lifted off my cock, and with a final tweak of the pocket rocket I let her dismount from my head. "That was a first," she admitted, clearing her throat a couple of times as she returned to her seat and picked up the cards. "I've sucked cock before, but never been able to deep-throat. I think it helped to have you play with the little man in the boat."

I looked at my dick coated with Annie's saliva. It was still blood-engorged from her throat and there was a faint hint of lipstick near the base. Annie saw me looking down and commented, "If that thing gets any bigger, it's going to burst on its own."

"I'll take that as a compliment," I said. In truth, I couldn't remember ever seeing it this size. It ached like a son-of-a-gun, but it was a good ache.

Annie passed out the cards and called Low. I got the 10 of Clubs, and Lisa and I took new cards. Annie won with the 3 of Spades and Lisa lost with the Queen of Hearts.

Annie was now in the position to fulfill her fantasy. "OK, Lisa, pinch those titties and get them ready for these," Annie ordered, indicating her nipple clamps that she was now removing. Lisa did as directed, and her nipples ended up turning bright red with the clamps sticking straight out. We could see that Annie knew that this somewhat grotesque position provided maximum pressure on the nipples. Lisa was clearly new to this form of exquisite torture was almost in tears from the sharp pain of the nipple clamps.

"Now pick up the vibrator, lick off Kia's juices, and coat it with the K-Y jelly," Annie next directed. Lisa reached down for the pink vibrator and gasped as even more blood flowed to her tits. She quickly stood and reached under each breast, gently lifting them to ease the throbbing pain. She tentatively licked the vibrator, and then sucked it thoroughly when she found the taste almost pleasant. Feeling sorry for her, I picked up the jar of lubricant, opened it, and handed it to her. Lisa pulled two fingers through the jar and spread the jelly on the vibrator.

Annie continued as she sat back down, "I'm going to lie back. You're going to kneel over my head. I'm going to put the vibrator in your ass and turn it on. I'm then going to use this," she held up the pocket rocket, "to take your mind off the vibrator. You can use this," she held up the double-headed dildo, "to distract me for the 5 minutes of this challenge. Any questions?"

Remembering my last challenge to her, I had one. "What happens if either of you cum?"

Annie quickly answered as she lay back on the carpet, "Nothing. I'm going to see how many times I can make Lisa cum, and I hope she does the same."

Lisa was looking at the silicone dildo. "Can I use both ends?" she asked.

"Yes, but only one per hole," Annie laughed.

Lisa walked around and placed a foot on either side of Annie's head. She eased herself down, handed the vibrator to Annie, and picked up the dildo. Lisa was now on hands and knees with her ass facing away from us. Both Kia and I moved around to get a better view as Annie placed the pointee end of the vibrator against Lisa's sphincter. As she pushed with more force, the tip entered and opened Lisa's butt hole. Annie pulled back and reinserted the vibrator a couple of times to release the pressure; with the lube, it became quite easy as Lisa began to relax her anal muscles. Finally the vibrator was buried in Lisa's ass except for the control, which Annie now turned. A deep humming could be heard as Lisa squealed. If Annie hadn't been holding the vibrator in place, I'm sure Lisa would have shot it three feet.

Lisa's arms collapsed and her head fell to Annie's crotch. Annie lifted her knees, spread her legs, and provided a cradle for Lisa's face. As Annie picked up the pocket rocket, Kia saw that Lisa needed help in finding the dildo, which had slipped out of her hand when she fell forward. She moved back to the card pile and knelt down face-to-face with Lisa, between Annie's legs. I watched as she lifted Lisa's head so that her chin came off Annie's dark bush and kissed the blonde with surprising intensity. Lisa returned the kiss and they locked tongues.

Annie reached back and grabbed my foot to get my attention. She winked and pointed to the vibrator, indicating that I should take charge of that while she worked the pocket rocket. I leaned forward and began to slide the humming toy in and out of Lisa's asshole. As I would slide it out, I would move the control end in an ever-growing circle, stretching the hole each time. When it was buried to the hilt, I would twist it to increase the friction deep in her bowel. Pulling out fully, I saw the hole gape for a moment before slowly closing to a cute puckered target. The vibrator went back in with little or no resistance.

I could see Annie working on Lisa's cunt when the pocket rocket would come into view as she moved from the clit to the vaginal opening. The hum from that toy, competing with the vibrator, would change pitch as Annie worked it around Lisa's pussy. Annie would occasionally lift her head to lick at the moisture forming in the opening and running down the inside of Lisa's thigh.

Since Lisa's head was in the way, all I could see in front of me was Kia's cute butt sticking up and wiggling as she and Lisa worked on Annie. Sliding the vibrator in one last time, I brought Annie's free hand up to hold it in place so I could see what was happening. As I moved around, I saw that each girl had an end of the dildo. Lisa pumped hers in and out of Annie's cunt while Kia was working hers into Annie's ass. They had set up a rhythm so that one would push while the other pulled. Lisa's hair was matted to her head; she had clearly had multiple orgasms from the combination of nipple clips, asshole reaming and pussy manipulation.

I moved behind Kia and looked at that beautiful cunt with huge lips dangling open. Her gaping hole and inner flesh provided a perfect target that I entered in one motion. I held still for a moment and let her get used to the fullness, then began to pump. After a tentative touch at her asshole got a slight wiggle of her hips, I spread her cheeks and worked my two thumbs slowly in. This allowed me to pull the sides open as I continued to plunge in and out of her pussy. I now could see into her ass and could watch the inner flesh move as my cock moved back and forth.

When I felt those inner muscles clench and saw the flesh deep in her ass start to pulse, I knew she was cumming. I couldn't hold back as the first pulse of jizz shot out of my cock. Again and again I felt my cum enter her, until I finally fell away in a sex-induced haze.

I lay there panting for at least a minute, listening to the buzzing of vibrators and the moaning of women. When the noises died away, I rolled over to see the girls in the last stages of their own orgasms. Annie had dropped the hand holding the pocket rocket at her side and was using the other to pinch and pull at her left nipple. The vibrator had fallen out of Lisa's ass and was lying next to Annie's head, still humming.

Lisa and Kia were again kissing, this time with one end (I'm not sure which) of the dildo between their lips. Kia had rolled over on her side, and was gently tugging on the chain, stretching Lisa's now-purple nipples. I lay with my head less than a foot from Kia's fine ass. I could see my white cum leaking out between those amazing pussy lips. Her asshole continued to throb involuntarily.

"I think it's your deal, Lisa," I groaned.