Strippers and Prostitutes Ch. 08

"So Rosie and I changed rooms, giving each other a hug as we passed. I also asked Rosie if we wanted to watch each other, because I love watching people make love whenever possible, and she said she was willing but didn't know about Damian. I didn't know about Jeff either, so we scooted back and asked the guys who were very happy with that arrangement. So all of us ended up in our room making love together on the big bed.

"I can't speak for the other three, but I found it really enjoyable and sexually arousing watching Rosie take Jeff's cock inside her while Damian fucked me deeply."

She paused, watching cocks come to attention all round.

"Anyway, to cut a long story short, Jeff and Damian both came hard, deeply embedded in the other's partner, then they each lay on the bed caressing their current lover for a while. Then Rosie and I decided we needed some more action and rolled together and started kissing each other.

"Jeff and Damian had a whispered conversation and Jeff headed into the Dungeon, returning after a couple of minutes with a double ended dildo and some string. Our clits were quite prominent because they are larger than normal and the sex we'd had made them even more engorged than usual. So Jeff and Damian each tied a piece of string around our clits, quite tightly so they wouldn't slip out, then had us lie together in scissor fashion, pushing an end of the dildo into each of our cunts. They then pushed us together so that our pussies were almost touching and tied the strings from our clits together. We could move a small amount, any more and we pulled on our clits painfully.

By now we were feeling very sexy indeed. Nothing like having your clit tied and a dildo in your cunt to turn you on, as you women would know. So we began moving together, trying to stimulate ourselves to cum without hurting our clits. The guys just watched fascinated and gently stroked their hard cocks while we wriggled and moved against each other. After about ten frustrating minutes Rosie came hard, screaming and writhing about, pulling on both our clits very painfully. I was so close that the added pain pushed me over the edge and I came hard also, continuing the painful experience as I pulled both our clits.

After a short time we both lay still, taking stock of our injuries while the guys untied our clits and we could roll apart and remove the dildo. Then Jeff fucked me hard while Damian fucked Rosie hard and they both came again quite quickly."

Rosie gasped, blushed deep red and said "Amy, do you have to? Please stop there."

"Sure I have to and no I won't stop, I'll tell the whole story," replied Amy, "It happened. Nothing to be ashamed about."

She then continued with her story.

"That left Rosie and I hanging, needing to cum. So we switched to a 69 and licked and sucked each other to very satisfying orgasms."

Rosie hid her face in her hands, blushing furiously again.

"Watching two gorgeous girls cum on each other's tongue is guaranteed to arouse any guy who's not a eunuch. So by the time we'd finished they were raring to go again, cocks standing to attention nicely, just as I see many are right now." She smiled as several guys tried to cover their obvious arousal.

"There was only one thing for it, more sex. The question was, who would fuck whom? So we tossed for partners. I won Damian so we fucked again while Jeff and Rosie watched and helped, Jeff massaging my tits while Rosie massaged Damian's balls. Needless to say we both came hard. Then it was their turn, with our help in a similar manner, and they both achieved massive orgasms. We then showered together and here we are. Temporarily fucked out and more than ready for breakfast."

There was spontaneous applause from all the listeners, many of whom were obviously ready for some action themselves. They drifted away from the kitchen, several couples, not necessarily in their established pairings, moving to the far side of the pool area where they could be seen meeting their obvious and urgent needs.

"That was a great summary, Amy," said Rosie as they ate breakfast, "Embarrassing, but great".

"Well, I thought we'd better tell them what happened otherwise we'd be hounded for details all day. Now we can get on with the day without hassles."

"Great idea," asserted Jeff. "Now, where to from here?"

"Well, I think this morning we need to be inducted into the polyamory group," started Damian, "And then I want to continue challenging myself, and hopefully Rosie as well, in the Dungeon for the remainder of the day. It's also great weather so a swim and sunbathe will be awesome at lunchtime. I'm guessing that we'll all be cumming in the Dungeon so there's really no need to schedule love making time today, that can be for tonight after or at 'Dana's' and we definitely need a final fuck swap tomorrow before we depart. Are you two getting pierced sometime?"

"Yes, we think so," replied Jeff. "I know that Amy wants her clit hood pierced so I guess this is a good time. I'm not into piercing really except on Amy, but she won't get one unless I have one also. So I think I'll have my cock pierced somewhere. I guess we'll need to have that done last thing so it doesn't limit our activities here so we'd better book quickly. How about you?"

"Yes, we're both keen to have it done, same places as you guys," replied Rosie. "Let's go and book straight after breakfast then we'll know when we can have a final partner swap before our sexy bits are put out of action for a while."

They booked consecutive appointment times between 2 and 3pm Sunday giving themselves time to catch their flights home Sunday evening and allowing plenty of time for their planned partner swap session. As they walked past the notice board Jeff noticed Amy's request for someone to whip her pussy hard.

"Hey, Amy, are you serious about this?" he asked.

"Yes, absolutely certain. I want someone, not you, to beat my pussy to a pulp, well, maybe not quite to a pulp, but certainly I'm OK if there is permanent damage including the possibility that I either lose my clit or it is put out of action. It's a long story and I'll tell it after I have been beaten. Don't try to stop me, I am determined that I need to face some demons and that now is the time to do it. I figured if I was going to be out of action for a piercing, I may as well be totally out of action and have this necessary cathartic experience. I see Todd has volunteered to help out. I guess my clit piercing will depend on whether I still have a clit to pierce by then."

Amy went to the board and wrote under Todd's offer "Thanks. To take place in the Dungeon at midday Sunday. Spectators welcome."

"There," she told Jeff, "All done. So we need to have our partner swap sex before midday."

"I hope you know what you're doing," said Rosie, "It's certainly not something I would like."

"Ah well, each to his or her own," replied Amy with a grin. "I'll bet you'll be there to watch though."

"Ooohhh yes, I surely will. I think everyone will. It's not every day you see a gorgeous naked pussy being beaten to pulp, as you put it. Maybe there won't be anything left to pierce," she joked.

"So does that mean sex is off the agenda for a while," asked a concerned Jeff.

"Yes, but remember your cock will be too sore from its new ring for you to be concerned. And just think how great it will be once we resume, assuming I still have a clit and pussy lips."

Marcie approached them. "Do you guys want to be inducted into the polyamory group now? She asked.

"Definitely," they replied.

Marcie went back to the kitchen area. "I have an announcement," she began, waiting for conversations to hush and lovemaking couples outside to pause. "Rosie, Amy, Damian and Jeff will be inducted at 11am this morning in the Dungeon, that's in twenty minutes. Everyone's welcome."

Conversation returned to normal and Todd came over to Amy.

"Are you happy with me whipping you tomorrow?" he asked.

"Oohhh yes, thank you for offering. I understand you're a master of the single tailed whip. Your reputation is amazing," replied Amy.

"So what brought this on?" asked Todd.

"Well, I've always liked pain and I find it very arousing. But until now I've just been whipped with multi-tailed pussy whips on my pussy and breasts. And Jeff is too afraid of hurting me to hurt me, if you know what I mean. So I figured this was a wonderful opportunity. I'll be out of action because I'm having my clit hood pierced, so I may as well be out of action for a whipping as well. There are also some issues that I need to deal with but I'll tell everyone about them after the whipping session, if I am still able, that is."

"OK, good reasons. So how much would be too much?"

"Well, it would be a bonus if all my bits were still intact when you've finished. But if they're not then that's also OK. If you cut my lips or clit off that's OK so you mustn't feel bad about it at all. I expect you to do damage like splitting my cunt lips and drawing blood. I'm sure that Marcie can take care of any stitching required. If there is any permanent nerve damage then that's the price I am willing to pay as is the loss of feeling or sensitivity in my clit or even the loss of my entire clit."

"That sounds like you mean business and would seem to be a pretty serious beating you're wanting. How about caning as well?"

"Yes, caning sounds fine to me. I guess that you can cane harder than whipping because the end of the whip can do a lot of damage as it exceeds the speed of sound sometimes, whereas a cane is hitting onto me rather than across my skin area. So while I do want the whip, caning would also be great please. But I do want the whip for the catharsis that I need."

"OK, so can I have a preliminary look at the target please?"

Amy sat down on a chair and spread her legs wide, Todd crouched down for a better view, pulling her lips apart to examine inside.

"How do you want to be positioned?"

"I want to lie on my back on a punishment table, with my body and arms strapped down. Then I want my legs folded back and held at the ankles only, pushing my pussy into the air, providing great access but also allowing me to hold my legs together or apart so that I know and people can see that I am opening my legs voluntarily rather than having them held apart. I also can't be gagged because I want to be whipped until I say the safe word and I want to hear my screams loudly."

"Hmmm, that sounds like an interesting challenge you've set yourself. How many strokes do you want?"

"Until I use the safe word or until I pass out. I can't predict how many because I don't have any idea how I will feel. I do know that when I am being punished I zone out, allowing myself to not feel the pain. I haven't quite got to the stage that Mom and Dana talk about where the pain is instantly transferred to sexual ecstasy. I guess this is another step along the way and hopefully that will happen, hopefully this weekend."

"OK, all sounds good to me. See you tomorrow at midday if not before. Enjoy."

Todd stood up and walked away, wondering if she would still be interested in doing this after the whip demonstration that he had scheduled at 'Dana's' tonight. He knew that sometimes the volunteer target had ended in hospital after these sessions, but was also aware that they had always thanked him profusely with gifts and sexual favours after they had healed. He thought, not for the first time, how strange people were and came to the same conclusion as before; people disliked monotony and would do anything, even very painful and dangerous things, to bring some adrenaline into their lives.

At 11am most people were gathered in the Dungeon for the induction. Amy and Jeff had chosen to go first and Amy was positioned over the tapered dildo, wondering how this monster was supposed to fit inside her. Jeff was crouched over the ten pound weights attached to his balls wondering whether they would be pulled off.

"Are we all ready?" asked Dana, who was supervisor once again.

Amy and Jeff nodded so Dana raised the dildo so its narrow two inch end approached Amy's pussy lips, rising to part the lips and continuing to enter her cunt. Dana stopped the dildo once it was about two inches inside and instructed Jeff to stand up, lifting the ten pound weight with his balls. Jeff felt the weight stretching his ball sac, pulling painfully on the cords inside as well as the surface skin. Still he stood, the weights dangling above the floor, a grimace of pain on his face as he watched Amy struggle to keep her feet together. Just let it happen, he wished so his ordeal could be over.

Amy tried to keep her feet together but with no sideways resistance from the floor they kept sliding apart. Already, after only a few moments, she felt her inside thigh muscles spasming from stress and knew that she wouldn't be able to keep her feet close to the pole for very long. She tried relaxing her muscles, feeling her feet slide sideways and her cunt drop further onto the dildo, spreading her pussy lips as it did so. There was no going back, she found, when she tried to bring her feet together and found that she could not move them. Well, she thought, if it was going to happen, then let it happen.

Slowly and as carefully as she could she reduced the tension in her thigh muscles, feeling and watching her feet slide slowly sideways, feeling the giant intruder thrust deeper into her cunt, stretch her pussy lips wider. She didn't react, instead feeling the sexual arousal that having such a huge dildo in her cunt brought to her. Apart from the stretching pain, it really wasn't too bad, she decided. She dropped lower and lower, inch by inch until Dana told her that she was two inches from the end. She felt like she would split in half, but also felt extremely aroused and, unbelievably, like she was almost ready to cum. These feelings of intense arousal dulled the pain and she released her thigh muscles, dropping quickly until the dildo hit her cervix.

The pain of this encounter brought her back to reality and she tried, unsuccessfully, to lift herself up. She wriggled her hips, dislodging the end of the dildo from her cervix, allowing it to penetrate a small amount further until it was resting, painfully but arousingly, beside her cervix. Her clit pressed against the curved guard. She was now fully penetrated by the dildo, she had achieved her goal, yet she was so close to cumming that she didn't want to stop now. Desperately she wriggled her hips, seeking the last tiny bit of stimulation to push her over the edge.

Dana looked on with some concern, as did Amy's parents, Gabby and Chris. By rights she should now be saying the safe word and it would all be over but instead she was wriggling on the dildo, obviously trying to cum. Dana approached her.

"Would you like me to rub your clit for you, Amy?"

"Oh yes please. I'm so, so close to cumming. Please rub my clit."

Dana rubbed her clit gently and Amy felt pulses like liquid electricity surge through her body and bounce back to focus on her clit, driving her towards a huge orgasm. She tumbled over the cliff, writhing, screaming, shuddering as she fell down the steep slope of orgasm. After a few moments she calmed down and the pain of her overstretched cunt and cruelly crushed clit came with a rush.

"Pomegranate, pomegranate," she cried, "Get me off this now please."

Dana supported her and lifted her as Todd lowered the dildo. Jeff crouched down, relieving the pain in his swollen balls and stretched scrotum as the weights rested on the ground. The rest of the onlookers burst into applause.

Jeff and Amy were freed from all restraints and hugged by family members as they went to lie on the bed to recover. They cuddled each other, Jeff feeling Amy's wide open cunt while she gently massaged his sore balls.

"That was so painful," said Jeff, "At least you got to cum."

"Yes, that was very nice but after I came and the endorphins left, the pain was unbearable. Sorry I took so long and made you hold the weights up for so long."

"That's OK, sweetheart. Just don't expect miracles tonight though."

"I'm sure we'll be fine very soon. The others all recovered quickly with no ill effects, so we will too."

Meanwhile Damian and a very nervous Rosie had been prepared in position.

"I don't want to go through with this," Rosie told Dana.

"That's fine," replied Dana, "But just be aware that you will be the only couple who haven't suffered this ordeal. Technically you will not be permitted as of right to fuck others who have gone through this. Just remember how much you both liked swapping partners this morning. Without this you possibly won't be able to do that again. No pressure though; it is and always will be your body, so your choice."

Rosie bit her bottom lip, knowing how much she wanted to fuck with the other guys here, to be a full and complete member of the extended family, yet how she dreaded pain. As she thought about this and the times she had suffered pain, she suddenly realised that the fear she had of pain was far worse than the actual pain itself. Here was her opportunity to overcome this fear once and for all. She made up her mind to do it and to enjoy and welcome the pain.

"OK, let's do it," she told Dana.

Dana gave her a hug and raised the dildo, again inserting it a couple of inches into her cunt. At the same time Damian stood up, feeling the weights stretch his balls. Immediately Rosie felt the tension in her thigh muscles and knew this would be a short trip down the dildo. She pushed the fear to the back of her mind, focussing only on the anticipated feelings of stretching and fulfilment that she wished to feel; the feelings of being a real woman accepted into this group. Her feet slipped sideways and she dropped onto the dildo. Without too much thought, she simply let it happen. She felt sharp pains in her pussy as the huge intruder stretched her lips and her cunt walls. Still she relaxed and dropped further.

Those in the group of onlookers who had seen this procedure several times were amazed how Rosie appeared to accept that dropping onto the dildo was inevitable, so dropping fast would get it over with fast. Dana was concerned in case she tore the skin at the entrance to her cunt because she was stretching it too fast, but there was little she could do at this stage.

Rosie felt the dildo ravaging her insides, going deeper quickly and spreading her pussy lips painfully. I guess this must be like having a baby, she thought. She continued to drop until she felt the rubber cup on the end of the dildo press against her cervix. Ouch, she thought, then quickly twisted her hips to reposition the dildo, allowing it to continue to sink into her until her clit pressing against the guard told her she was there.

Whew, she thought, made it. Now what? She tuned in to her body, feeling how her cunt and lips really felt, relaxing as she let go and just accepted what was right now. She examined that part of her that held the fear and found that in the achieving of the goal, the fear had disappeared. So that's how to overcome fear, she thought.

She came back to the present. Opened her eyes and saw Damian holding up the weights with his balls, his eyes pleading with her to say the safe word and end his agony.

"Pomegranate, Dana. I think we're done here now."

Dana was amazed by Rosie's performance and wondered where she had found the inner strength to carry out this induction in such a majestic manner. She made a mental note to have a chat about this with Rosie sometime, but meantime she supported Rosie, Todd lowered the dildo and Damian set the weights on the floor with a sigh of relief.

Once they were both freed from their means of torture, they walked arm in arm and sat on the bed beside Amy and Jeff. They quietly discussed what had happened, each of them feeling the wide open cunts of the women and the swollen balls of the guys.