Postscript It took almost two days for me to find the right piercing shop to get Jess what she wanted. Even at that the guy at the shop thought she might be just a little crazy to do all four at once.
He did suggest some loose clothing, that would be fairly lightweight, since she would be tender for a day or two. Jess selected a loose lightweight dress and I picked her up and took her to the shop. When we arrived we spent a few minutes deciding on exactly what she wanted, then the piercer told her to get undressed and lay down.
Jess simply unbuttoned the top of the dress and dropped it to the floor. Beneath it she was naked, something I had not expected at all. She lay down on the table and opened her legs, since the idea was to start at the bottom and work up, assuming that would be the best order to start with the least painful, although most private first.
He swabbed her pubic mound and prepared her then asked if she was ready. When she nodded yes he immediately punched the rod through her clit hood. She barely flinched and when he was done he looked at his handiwork and smiled. "Such a beautiful pussy. Thank you for letting me pierce it." "Thank you for piercing it.
We love the way it looks too, don't we?" And she looked up at me. "Yes, her husband and I only like one thing better than looking at her pussy and that's fucking it." Jess blushed furiously and shot me a dirty look.
The piercer just smiled and went to her navel. "This may be more painful than your nipples. It is for some and not for others.
Once it heals you can put almost any decoration you want in, but for now we're going to use a simple stud, just like an earring." He swabbed while he talked and was ready in moments.
When he asked if she was ready Jess answered with a "Yes" and it was done also. "That hurt, but not too bad." She admitted. He moved to her right nipple and prepared it.
When he was ready she was too and he pierced. Jess bounced on the table and I thought I saw a tear, but she also flushed, so I was wondering what was going on.
We changed sides of the table and he prepared her left nipple. I was looking down at her when he pierced and was surprised to see a squirt of fluid between her legs and her back arch. The piercer evidently saw it too. "Did you have a little accident honey?" I could tell by the look on Jess' face what it was. "No, she came, and she often squirts when she cums." I answered. Jess blushed even more and looked at the piercer.
He said, "I've never had anyone cum when I pierced them before." I walked down to the foot of the table so I could look and admire all Jess' new hardware at one time. "She is one special lady in so many ways. That's why we agreed to have her pierced and have you make the weights for these." He looked down at Jess.
"Now don't you let them hang any weights on these until they're fully healed. That'll take close to a month, even if you take real good care of them." He admonished. "Keep the top three covered for a couple of days, except when you manipulate them, and don't let anyone get spit on them for at least a week. Your ears are pierced so you probably remember the drill for that, but keep them clean, free moving and keep an antiseptic on them until they heal." Jess smiled up at him, and reached to touch her new clit piercing.
"I like this. Can I look?" "Sure, stand up, carefully though. The mirror is over there." He pointed. Jess walked carefully over by the mirror and stood with her legs parted. "I like these." When the piercings were covered she picked up her dress.
"How soon can I fuck?" "As soon as you're not trying to do it on my piercing table, if you really want." "Then I guess I have to put my dress back on." Jess smiled at him with her legs open, and I thought for a moment she was going to invite him to try his piercing table out with her, but she stepped into her dress and buttoned it.
"I think Tim is going to love this. Let's get home and get him some pictures." On the way home we talked about getting her a chance to eat pussy without knowing too much about the people, so she could relax and enjoy the sensations. She also wanted to try more than two men, and I suggested doing something so fully costumed that it wouldn't necessarily be "her" that all those people were having sex with.
After I explained the idea she was excited, but by the time I got her home she was really starting to hurt. We didn't have sex, in fact, she went home, slipped out of the slightly heavier dress she'd worn and into the absolute minimum she could that put no pressure on any of her new decorations. We didn't even take pictures. It was a couple of weeks later before she called and said that she was feeling much better and needed me to come over. I stopped, even though I didn't "have" to and spent the evening.
She still wasn't fully healed, but she did want a cock in her. And she wanted something else. Once we had the little guy in bed she asked me to bring in my toy bag with the paddles. She took me upstairs and dropped her clothes on the floor, and looked at me. "I want you to leave a paddle for Tim until we can get our own." She told me.
"But I know you have several, and I want you to help me decide which one to keep." As she started to remove my clothes. "And how would I help you decide?" I asked, coyly. "Silly. I'm going to bend over the foot of the bed and you're going to give me about five whacks with each one. When we're finished I'll decide which one I want." "You mean which one hurts best?" Jess blushed. "That's exactly what I mean. As she pushed my pants to the floor, freeing my erection.
"Oh, goody. You want this too!" "He's thinking that he'll get inside you before the night is over, that's all." "If you paddle me right, he will." She grinned. Then she looked into my eyes and sucked my cock into her mouth. My knees nearly buckled as the head went into her throat.
"I thought I had to paddle you first?" I gasped, when I finally could. "Oh, you do. That's just a promise to make sure you do it right." She grinned. "Now how do you want me?" "Put your hands on the foot rail and move your feet back until you are bent at the waist with the weight on your arms and shoulders." She complied so that her back and arms were in line and her hips thrust in the air.
"Perfect." I said. "Now I'm going to put a little oil on your ass and give you a few whacks with my hand to warm you up." I explained while I laid the paddles out on the bed in a line. When I finished oiling her ass cheeks I told her to prepare herself and started alternating whacks from one cheek to the other.
After five each I paused and reached for the first paddle. "Okay, Jess. This first one is more what I call a punishment paddle.
It's a little longer but somewhat stiff. Since it reaches all the way across we'll just do five with it. Ready?" Jess nodded. I looked and said, "No, ask me." "I'm ready. Please paddle me with five strokes." "Very good baby. Five it will be." I raised my arm and delivered the first stroke firmly. Jess jumped a little and I delivered the remaining four. When I finished Jess was flushed but steady. "What did you think of that one?" She contemplated for a moment.
"I like it, but there's no real sting to it. I suppose if you hit hard enough, but I'm not sure that's what I want." "Okay, this second one is a bit different." I held up the next paddle.
It looked like a long handled ping pong paddle, with a larger than normal paddle. "This is another fairly rigid paddle but coated to give a little more sting and a little less coverage. We'll use five strokes each side with this and I'll alternate. Ready?" "Yes, please give me five alternating strokes." I raised the paddle and brought it down sharply on one ass cheek, then switched to the other.
Each time I got a satisfying smack. When I'd finished I looked down at Jess and she was definitely excited. "How was that?" "Much better. It gives a nice sting, but it's not exactly right." "Okay. This third paddle is similar." I said holding it up. "But it has holes drilled to give it a bit more sting and flex. I think you'll like this one. Ready?" "Yes. Please." Jess said, with some excitement in her voice.
I brought down the first stroke with a much more satisfying "pop" and followed it with more. I watched Jess' ass and cunt and could see that the additional sting was exciting her as her cunt lips swelled and reddened noticeably by the fourth stroke. When I administered the last her knees buckled slightly and a trickle of cum ran down the inside of her leg. "That was obviously better." I said as I watched her steady herself while the cum ran to the carpet.
"Yes. I like that a lot." She smiled. "What's next?" "This next one is similar to the last in size, but instead of holes has been shaved thin to make if more flexible. For much the same reason as the last one, obviously." I picked it up and prepared myself.
"Five more strokes each side. Ready?" "Oh yes! Please more strokes." I brought the paddle down sharply, alternating ass cheeks again. Jess made no attempt to hide her excitement. When I delivered the last stroke a squirt of cum flew from her cunt and wetted the carpet between her feet. That was two orgasms just from being paddled, and I still had two paddles to go. She must have been watching because she smiled up at me and said, "Oops." When I laid that paddle aside and picked up the next.
I might well have said "Oops." myself because that was when I noticed that my cock was throbbing between my legs and pointing directly at her. "This next one is a combination of the best features of the last three in my mind. It's longer, so one stroke will cover both ass cheeks, but it's also very flexible and to make it sting more it also has holes drilled in it so it gives a very sharp sting." I explained. "Are you ready for five more?" "Oh yes. Please, at least five.
Can I have more?" "How many would you like?" I asked. "Remember, this one will get both cheeks." "Ten. Please? Can I have ten?" "Your wish is my command. Ten strokes it is." I applied the first and Jess quivered. As I counted the strokes she began to quiver. At nine I thought her knees might buckle. At ten they nearly did. A larger squirt of cum left her cunt and she nearly went to her knees before she caught herself.
Her eyes were shut tight and she was quivering violently. At first I was concerned, and then I realized that she was having a strong orgasm. I stood quietly while she got herself under control. She looked at me, smiled and whispered, "More? Please? More?" "The last one is more a crop than a paddle. It's long, thin, flexible, and is designed to give a powerful sting when applied with force.
I will give you five again." "No. Please, more?" "How many then?" "Until I ask you to stop?" "Is that really what you want?" "Yes. Oh yes. Please?" "Then until you ask me to stop." And I brought down the first stroke across that beautiful ass. I didn't bother to count, I just kept applying the crop to Jess' ass.
Suddenly she moaned loudly, quivered and collapsed to her knees. Her cunt flooded the carpet. She dropped her hands from the top rail to the bottom rail.
She tried to look at me, and whispered, "Fuck me. Please, please fuck me." I knelt behind her and rubbed my cock along her cunt lips and started to push in. "No, in my ass. Please." She begged. "Fuck my ass. Please. Fuck my ass, please." I raised the head of my cock, placed it against her anal ring and pushed forward. She accepted me inside and pushed back to engulf my cock with her ass.
The heat from her ass cheeks had me nearly ready to cum immediately. I started to stroke slowly, but she looked back and begged again, "Pound my ass. Fuck me like you mean it!" I complied and started slamming myself into her. I reached around and grabbed at her clit and rubbed it. She was cumming again instantly. I slammed into her ass as her ass milked at my cock and I couldn't control myself.
"Oh god, baby, I'm cumming. I'm cumming!" I slammed into her and drove her to the floor as my balls drained themselves into her ass. I collapsed on top of her and we lay there locked together for several minutes, unable to move.
I recovered just enough to roll to the side and hold her in my arms, with my cock still pinned in her ass. Jess finally stirred, opened her eyes and looked back at me. "Oh my god! I have got to do more of that!" "Tim is going to be a very happy man when he gets home." "Can I still have both of my cocks?" "I'll make sure you can have both of your cocks from time to time." I smiled.
"Maybe we can even arrange for more than two. And I still need to get you some pussy to eat." Jess' ass gripped my cock and I jumped. "I love the sex like this. It just makes me want more and more." "I understand, but Tim may have to tile the bedroom floor if you keep this up." Jess blushed.
"Sorry about that." "Nothing to be sorry about. We're both delighted that you enjoy yourself so much and cum so hard. We look at it as a tremendous compliment that we can either or both make you cum so hard that you squirt like that." "Feels like I'm not the only one who did some squirting today." "Do you mind?" "No, silly.
Even as hard as you made me cum I could tell you were cumming just as hard. That's quite a compliment back." She smiled. "You know I'm going to have to let you take my cock out of my ass." "Your cock?" I twitched it in her ass. She jumped this time.
"Yes, my cock. Do you have a problem with that?" "You might have to argue with Judi." "There is that." She agreed. "I have to get up or the mess is going to get a lot bigger." I opened my arms. "Oh heck. You didn't have to let me." "You said I did." "I know." She admitted.
"Can you hold me again and roll over on your back? Without taking my cock out, that is." "I think so." I wrapped my arms around her and rolled over onto my back. "Better?" "Not really. I don't want to let you out of me but I have to. Damn! I'm going to sit up now, then get up." "Okay." I unwrapped my arms again. As she sat up I gave her a push with my arms. "Ready?" Jess looked back over her shoulder.
I nodded. She stood. And ran. I sat up slowly and followed her to the bathroom to clean up. When we were finished we curled up in bed for a little while. Jess lay her head on my chest and stroked my cock. "What's it like to make love to a woman?" "It's like heaven." I said. She looked unhappy. "Are you asking what it's like for a woman to make love to a woman?" "Yes." "You could ask Judi." "Why?' She paused.
And blushed. "You mean she&hellip.?" "Yes." I explained. "She likes little, tight, dark-haired women, and I believe she's very good at making love to them." "Oh." Okay, wait for it. "Oh, oh!" "I asked her and she denied that had anything to do with it." "Do you believe her?" "Not entirely." I admitted.
"Although you would have to make an initial advance now or she'd do nothing. She cares too much for you and Trenton to risk your friendship." "Then I guess I should make sure I like making love to women first." "Probably a good idea." "So what's your plan?" "How many people are you comfortable with?" "I'm not sure." "Okay, let me start with this.
I'm thinking of inviting several couples. I think four or five. They'll know what's going on, and you'll be in on the selection process. We'll select a night that's good for you and we'll get them all here. Everyone will be naked, including you when we first introduce you.
Then we'll put you in costume, so that it won't be Jessica any more, it'll be a character who was you once. Then we'll re-present you as this character and everyone except Tim and I will take turns making love to you, and you to them, men and women both, as this character, of course. When they're done we'll send them home and Tim and I will make love to you together." "Will you and Tim make love to the character or me?" "It'll be your choice, but I think you." "Ten people?
I know the men will be no problem." She smiled. "That's a lot of cum. But five women. What if I don't like it after all? Or what if I'm lousy with women?" "Well, you are a woman, so you know what a woman will like, and they really won't do anything that Tim and I don't do almost every time we're together with you.
They'll just do it way better. And of course you love the taste of your cum on us, why wouldn't you enjoy the taste of another woman?" "Let's try it then. What kind of animal were you thinking of?" "I'm thinking of a bird." "Why a bird?" "Because the posture is right to make access to you easy, and if we build the costume right you won't be able to see any part of yourself when you're in it, but you'll still be completely accessible to everyone." "What would the costume be like?" "I think there would be several pieces, obviously.
A set of high boots for your legs to make them look like a bird's. A hood that will cover your head and much of your face, wings for your arms, and some sort of a drape that would cover your back and chest. Of course we'd have to have a tail, but it would have to stay out of the way when the guys were fucking you." "How would you do that?" "I think I know.
My idea would take care of two things at once." "What two things?" "Keep your tail erect so it's out of the way, and keep the guys out of the hole that Tim and I use." "Oh." Jess blushed.
"I hadn't thought about that." "I didn't think you'd want a strange cock in your ass in the middle of something like this." "So how do I make sure I get all their cum?" "I assume they'll put it inside you, and then you'll suck their cocks clean." "But won't I waste what runs back out?" "Are you saying you want all their cum in your mouth?" "Maybe Tim could catch it in something so I can drink it?" "Would that turn you on more?
Having Tim catching guys cum in a bowl while it drips from your pussy." Jess moaned. "Yes." "You are a very naughty girl." "It's all your fault." "I'm not sure I can argue that, although I seem to remember being invited to fuck my best friend's wife while he was gone." "Since you're hard again and I want you inside me I'm going to invite you to fuck your best friend's wife again. Would you like to do that?" She grinned at me. "Why don't you just climb up here and sit on that cock and we'll see what happens?" Jess sat up, flipped her leg over me and plunged down on my cock, facing away from me.
She stretched her legs out and spun herself around on my cock until she faced me and grinned at me, a foot on each side of my head. She squeezed my cock with her cunt several times and smiled. "Do you like a spinner?" "I certainly like this spinner." "That's good." And around she went again. When she was facing away from me she tucked her legs under her and looked back over her shoulder. "Are you ready?" "I'm almost afraid to say yes." I admitted.
"Ready?" "Yes." Jess grabbed my balls in her hand and lifted them, stuck a wet finger deep in my ass and started to hump on me rapidly. Next thing I realized we were racing to another huge orgasm.
She arrived just seconds ahead of me, screaming my name and pounding herself on my cock. She pulled the cum from me while I bucked my hips trying to get deeper inside her, screaming her name too. As she came down she drooped until her head hit my legs. She never pulled her finger from my ass, but she did sit part way back up, looked over her shoulder and smiled.
"Remember what comes next?" I smiled back. "Yes, I remember." She lifted her pussy off my cock and slid up to put a leg on each side of my head. She lowered her dripping cunt to my mouth and plunged my cock down her own throat. I buried my tongue between her cunt lips and cleaned her out while she licked our cum from me. She had one small orgasm from my mouth but she never took her mouth off my cock.
I thought I was going to have to pry her off my cock, but I finally begged and she let me out of her mouth. I offered to take a better set of photos of her new piercings for Tim and she agreed. We got out the digital camera and I took several, both close-ups and wider shots showing more than one at a time. We hooked up the camera and downloaded the pictures. She had done some herself and Skyped a few, but this was Tim's first chance to see a really good close-up.
Jess e-mailed the photos and then we called Tim to make sure he downloaded them. He loved the pictures but was even happier when Jess explained the plan for her costume party. Jess explained that her new piercings were nearly healed and I told Tim about the set of weights I'd commissioned to hang on them.
He was excited, and finally slid the chair he was using back far enough to show us that he was jacking himself off.
Jess wanted to know if she could help, and after considering it for a few minutes Tim asked me if I'd bend her over the desk, in front of the camera and fuck her for him. Of course we readily agreed, and I was pleasantly surprised to realize I was hard enough already. As soon as Jess leaned over the desk and locked her arms so the camera could show Tim everything I slipped my cock inside her and started stroking her. She was already very wet and we went right after it.
Jess was focused on watching Tim handle his cock, while Tim was looking at her face and watching her tits bounce while I slammed into her pussy. I moved my hands from Jess' clit to her tits and back and she quickly approached another orgasm.
She watched Tim in the monitor and asked him if he was close to cumming. Tim acknowledged that he was close and Jess said, "Please join me baby.
Cum with me. Cum when I cum, I want to watch your cum.
Please baby?" Tim and Jess started moaning together, then suddenly Jess said, "Oh god. Tim cum now. Please. I'm cumming, I want to watch you shoot your cum." Tim moaned long and deep, then shouted, "Here it is baby. Watch me cum." He shot up and across his belly and chest, several long shots streaking his body. His cum slowed and so did Jess. Me, I had quietly pumped another load deep into Jess' cunt while she was cumming too. As Tim held his softening erection, milking the remainder of the cum from it he looked at me and asked, "How about you Rich?
Did you cum in my wife again?" Jess giggled, "Oh yes. He gave me a cuntfull of his yummy cum.
Do you want to watch me eat his cum?" Tim moaned again, "Yes." Jess told him, "Then lick your own and you can watch me lick his." Tim didn't hesitate. He scooped up a handful off his belly and put it in his mouth.
Jess reached between her legs and caught a handful of ours and did the same. "Is your cum good, Tim?" "Yes. It's okay." "No honey. Your cum is luscious. I love the taste of your cum. I can't wait to drink your cum again. Can I have your cum to drink?" "You can have all the cum you want baby." "I don't know.
I want a lot of cum." Jess scooped another handful of cum into her mouth. "You can have all the cum you want." "How about if I want more cum than you and Rich have? How much cum can I have?" "If you let me watch you can have all the cum you can hold baby." "I can hold a lot of cum, between my pussy and my mouth. Are you sure you want to see me have that much cum?" "Yes. Yes I'm sure. I want to see you have all the cum you can hold. I want to watch you learn to eat pussy.
I want to paddle you until you have a screaming orgasm from the paddle. I want to do everything with you that pleases you and makes you happy. And I know that orgasms and eating cum make you happy, so you can have all the cum you can hold baby." "Will you catch the cum that drips from my pussy in a cup so I can drink it and not waste any?" "Baby, I'll watch their cocks going in and out of you so that I don't miss a drop.
If you squirt when you cum I'll catch that too. I'll bring the cup to your mouth so you can drink all the cum and I'll go back and catch more. And when you've had all the boy cum and girl cum you can hold I'll take you to our bed and make love to you so that you know that I have the best cum-loving wife ever." The way Jess clenched told me that just listening to Tim's words had made her cum again. She opened her eyes and smiled. "Thank you Tim. At the end of the night I want your cock to finish me off.
I want your cum in me when I go to sleep, always. I love you Tim." "I love you too, Jess." Tim disconnected. Jess turned to face me. She kissed me deeply, pulled back and smiled. "Thank you for everything you've given me. Given Tim and me." I started to argue but she put her finger to my lips. "No. I was a hung-up, spoiled little bitch and I didn't treat Tim the way he deserved.
At first I thought I'd get back at him by fucking you. But I was wrong. You made me think about my body and sex in ways that I should have a long time ago. You've made me crave having Tim's cock in me. You've made me want to try making love to a woman, because Tim will like that, and I know I will too.
You've shown me how to have orgasms in ways that I never imagined were even possible, and ones that just blow my mind at that. Three months ago I'd have never believed I would cum so much or enjoy it so much, and it's all because you have been a patient, loving teacher and friend." She moved her finger from my lips and kissed me again. "Now, I have a cock to clean." And she dropped to her knees and swallowed me. When she had licked off every possible drop of our juices she stood back up and kissed me again.
"Two weeks until the weights are done. Right?" "Yep." "Good. Just in time for Tim. Can you and Judi watch Trenton that first night?" "You have something planned?" "Yes. And if Tim can make me scream as loud as I hope I might scare Trenton, so it might be best if he stays with you." "Won't he want to be home with his daddy after four weeks?" "Silly, he likes staying with you almost as much as I like staying with you." Jess laughed.
"We'll go out for a while and get some dinner and drop him off, then Tim and I can come back here and play with our new toys." "You are a very naughty girl." "Yes. Thank you. I hope Tim knows just how naughty so he can give me the paddling I deserve." She thought for a moment, "And then the fucking I deserve."