Jill's Weekend
written by:
mcerotic

This is a continuation of the Podiatrist/StadiumGirl series. They have set up a high-end escort agency. Jill is about to go on the first weekend. Nobody really knows how it will go.

Jill here. It seemed our Ultimate Weekend finally had its first client and I was the girlfriend he wanted. Actually, I wished it had been Rebecca who went first, she is the most experienced at living this sort of life. She could fine-tune the experience more easily than me.

I'd been sent to someone precisely twice before. Once to Eric, for my first anal. I'd met him at the orgy where Rebecca seduced me, if that's the right word. Fucked him even. So the worst thing about going to see him again was that Rebecca had given me very specific instructions and I was an anal virgin so I didn't really even know what I was doing. But I was comfortable.

Then she sent me to one of her friends. A total stranger. But he was only a total stranger to me, Rebecca knew him well. Plus it was only for a few hours. Well, in fact his wife came home and I thought I was in trouble, but she was okay with it all and we ended up all going to bed together and I stayed until morning. It was actually pretty cool to sleep with a husband and wife.

But this was different. I was going to meet a guy who was a stranger to us all. Not just for a few hours, for a whole weekend. Not just for sex either, although for sure that would be involved. I was to be his girlfriend, show him the city, take him to dinner. He was paying thousands of dollars for the privilege so it had to be perfect.

Rebecca dressed me. Not literally, but she instructed me what to wear. The miniskirt we bought together, heels but not insane ones, a loose top. At least she let me wear panties this time. But she also had thought of something I hadn't: she told me to take my engagement ring off.

Eric would pick Jason up at the airport and drive him to the hotel, the St Regis. He would get to check his ID, get him to sign a contract, and collect the money in cash. Then he'd leave and text me with the green light, and I'd meet Jason in the lobby bar.

I was waiting nearby. I got a text saying it was time to go in. Then a photo of Jason, so I knew what he looked like. He was much younger than I expected. I thought I was going to be fucking a fifty-year old but he couldn't have been over thirty. To be honest, he looked pretty good. If he'd hit on me in a bar, I'd probably have given him my number. Well, before I got engaged anyway.

I went in. He stood up. I put my arms around him and gave him a hug as if I really was his girlfriend meeting up with him again.

"Would you like a drink?" he said.

"I want whatever you want," I said. Best to be clear from the beginning.

"Are you nervous?"

"A little."

"Then I want you to have a drink. We can get to know each other a little. So what's the first thing you have planned?"

I looked around to make sure nobody was close enough to overhear. "I'm going to go with you to our room, and suck you off before dinner."

He gasped. I think he found it hard to believe words like that coming out of the girl in front of him, especially in an upmarket bar.

"I thought it best to do something before dinner. We'll be so much more comfortable with each other afterwards."

"I guess," he said a little doubtfully.

"Then we come back down," I continued. "We're eating in the hotel restaurant tonight. We thought that was easiest in case the plane was late. Or you wanted more before dinner."

"More what?"

"More sex. Or you can have that after dinner."

"Wow," he said. "You don't beat about the bush."

I laughed. "No. But I hope you are going to beat about mine." I leaned a bit closer. "Except I'm shaved for you."

I glanced at his pants. He already had an erection.

I sat back innocently as the cocktail waitress approached. He ordered a cocktail. It was tempting to have one too, but I needed to stay in control so I just had a small glass of wine. She went away to get the drinks.

"You are even hotter in reality that in the photos on your website. You're stunning."

"Well, thank you. You are pretty good-looking yourself."

The cocktail waitress approached with our drinks, so we both sat quietly for a moment.

"When I heard you were a New York financial guy I assumed some grey-haired fifty-something guy."

"Nope. Not even thirty. How old are you?"

"Isn't there some rule about not asking girls their age? But I'm twenty-five."

"Is Jill your real name?"

"It is. It would make things really difficult if I used a pseudonym. If we had to book airline tickets or when I get carded. Plus I'd forget. So you really do have a girlfriend called Jill this weekend."

"I'm so looking forward to it."

"I don't think I've ever had a conversation like this," he said. "Especially not in a location like this. With a girl I just met."

"I just wanted to be clear with you. I'll do whatever you want. Whatever."

"I don't really know what I want. I'm so busy I rarely have time for dating and my relationships don't last. I've only had very vanilla sex."

"Now you can have 31 flavors."

He drained the rest of his martini.

"Take me upstairs," I said. "I can't wait to suck you."

We went up in the elevator and into the room. I put my arms around him and kissed him. I was his girlfriend, after all. I put my hand on his crotch. I could feel his hard cock through his pants.

"I have a request," he said.

"Yes?"

"I want to see you naked. You are so hot. I can't wait until after dinner for that."

I took him over to the bed. "Sit," I said as if he was a dog. He obediently sat on the bed. I went to the TV and found a music channel and put on some soft music. Never in my life had I ever stripped before. When I have had sex before either I just undressed, or I let the guy undress me.

I stood in front of him. I moved my body with the music and slowly pulled my top off over my head. I decided to go in a non-traditional order. The next thing I did was reach up under my miniskirt and pull down my panties. I let go. They ended up around my ankles of course. I stood there swaying to the music, letting him imagine my bare cunt under my skirt, a cunt I knew he couldn't wait to see. I used to think cunts were pretty ugly, to be honest, but now I've licked a few they have suddenly got a lot more attractive. I turned away from him, reached back and undid my bra. My back was bare. I dropped my bra to the floor, covered my breasts with one arm and turned back to face him. I could see desire in his eyes as I stood there wearing just a miniskirt. I moved my arm away and let him see my breasts. I turned away from him again, reached back and slid down the little zipper of my skirt, then I worked it over my hips. It was quite tight. He got to see my ass as my skirt fell to join my panties. I kicked off my heels and stepped out of the puddle of clothes, still facing away from him. Finally, I slowly turned to face him and he got to see my slit for the first time.

"You're gorgeous," he said. "I've never been with a woman...I mean had a girlfriend...who is so beautiful."

"Get your cock out," I said. He clearly liked being told what to do. In a trice he had his pants and underwear off. I moved over in front of him. I rubbed my mound against his cock as I unbuttoned his shirt and pushed it off so he was naked (well, he had his socks on). I kissed him. Then I planted a trail of kisses down his chest. He may not have time for girlfriends but he clearly had time for working out. I gently bit on each of his nipples before descending to his cock. I used just the tip of my tongue to slide the entire length of his cock, paying special attention to that little sensitive fold of skin just below the knob.

"Oh my god, you know how to tease a man," he sighed.

He'd shaved his balls for me so I repaid the favor by going back down and licking them. I assumed he'd been sucked by previous girlfriends, but I decided to do something that they probably hadn't. I pushed his legs up and slid my tongue lower until I reached his asshole. I started to tongue him there, hard.

"Oh shit, what are you doing?" he moaned.

I didn't answer. I just pushed a bit harder and got the tip of my tongue inside. I felt like such a dirty girl, I don't think I've done it before. He clearly loved it. He was making noises like a cat purring, making tiny movements with his hips like he was fucking my tongue with his asshole.

I moved back up over his balls, all the way up his shaft and finally took his knob into my mouth. I started to swirl my tongue around him.

"Oh no," he said.

He came instantly. I moved my lips up and down his cock as I felt my mouth fill with his cum. I didn't spill a drop. I opened my mouth to show it full of his cum. For some reason men seem to like that. Then I swallowed it and opened my mouth again.

"All gone," I said. "The perfect appetizer before dinner."

I stood up in front of him where he sat on the bed and kissed him. Sometimes a man is reluctant to kiss after you have just had his cum in your mouth but he kissed me back enthusiastically.

"You'll last longer next time," I said. "Now we've got that first time over with."

I stood up. He looked me up and down. Suddenly he saw my tattoo.

"What's that? It's like Schindler's List or something. A number tattooed on you."

"It's my owner's phone number."

"Who's your owner? What does he do?"

"It's a she, actually. You've looked at our website so you've seen her. Rebecca is my owner."

"What does that mean? What does she have you do?"

"Well, the most obvious thing is that she has me lick her and make her cum. Or she makes me give her my cunt if she is in the mood to do the licking. From time to time she spanks me or whips me. She doesn't like it to be pleasure all the time. When I go to her I never know if it is going to be a black day or a white day, pain or pleasure."

"Oh my."

I turned around. "Can you see the marks? They've almost gone but if you look closely you can see the stripes."

"Isn't it painful?"

"It hurts like hell. But my body loves it for some reason and I get so turned-on. And when she kisses me afterwards it is ethereal. You have no idea until you try it."

"Really? It sounds a bit extreme. Are you going to spank me this weekend?"

"If you want me to."

"Shouldn't you spank me even if I don't want to? Isn't that the point?"

"I suppose. I certainly never ask her to whip me."

"Does she tie you up?"

"She hasn't yet. I'm sure she will one day."

"What else does she do?"

"She sends me to people."

"How do you mean?"

"I have to go to their house. Sometimes do what my owner tells me. Sometimes do whatever the person or people I'm visiting want to do to me. Suck them off. Lick the woman. Let them do me anally."

"You do anal?"

"Of course. I know it is pretty intense but it's special too. Have you never done it?"

"No, never."

"Do you want to?"

"I suppose. The idea's pretty hot. Maybe just because most girls won't do it."

"I never did it until my owner made me."

"She did you anally? Like how?"

"No. She sent me to her own owner, and he did me anally."

"She has an owner too?"

"Yes. She has his number on her pussy. Like mine. Letting your owner tattoo you, being numbered Rebecca calls it, is total commitment. Every lover you ever have will see it."

"Wow. I know so little about this sort of thing."

"It was an eye-opener for me too. I was like you. I've had my share of boyfriends, of course. Lick, suck, fuck. Nothing more. With one guy at a time. No girls, no threesomes, nothing like that."

"Will you...I don't know quite how to phrase it...but will you just take over for the weekend? Instead of asking me what I want, just give me what you think I should have."

"You want me to be your owner, not your girlfriend."

"I suppose."

"If we are going to do this you have to obey. It requires total commitment. You do what I say even if you don't want to."

"Such as what?"

"For sure I will spank you or something similar at some point during the weekend. As you said, whether you want it or not."

"I suppose. There's a world I never knew existed and I realize the only way to explore it is to give you complete control."

"Exactly."

"OK."

"That's too casual. Say that you commit. That you will be obedient to your owner all weekend."

"I commit. I'll do whatever you say. Gosh, you'd better not get me into trouble."

I laughed. "Don't worry. Like Spiderman, with great power comes great responsibility. I also have to keep you safe and make sure you have a wonderful weekend. An ultimate weekend."

"So what do we do now?"

"Do you want to have dinner or do sex stuff?"

"Don't you decide that?"

"OK. Dinner. But wait."

I went over to my purse, I got out a sharpie indelible marker and came back. I took hold of his cock and stroked him until he was at least semi-hard. Then I wrote my phone number down the length of his cock. He was numbered, even if not truly permanently. I idly wondered if a sharpie was indelible enough to survive a weekend of fucking.

We went down to dinner. The weekend was not going at all how I expected. I had assumed I would do my best to simulate a true girlfriend, almost romantic. Obviously we'd have sex, but it would be whatever he wanted as my boyfriend. If he wanted affectionate loving sex, I'd do that. Of course, if he wanted to do something dirty like fuck my ass, I'd give it to him. Instead, after only a couple of hours, he'd ended up numbered, with my phone number on his cock. Now we really had to re-plan the whole weekend. It's not like he was going to be giving me roses any more.

I excused myself and went to the restroom. Luckily there were no other women in there. I called Rebecca and told her what had happened. She said she'd do some research and start to come up with a new plan for the weekend. She'd text me.

After dinner we went back up to our room. He tried to kiss me once the door was closed but I pushed him off.

"No," I said. "Your owner decides when you kiss. Right now she wants to see you naked on that bed. Stroking yourself. I like watching that."

I could sense disappointment at not being kissed immediately but he did as he was told. A moment later he was on the bed. He was already hard. To tell the truth, he'd probably been hard all through dinner. I slipped off my panties and kicked off my shoes. Then I got onto the bed and squatted over his face and pushed my pussy against his mouth.

"Lick me."

Rubbing my pussy on a guy is so different from a girl. All the rough stubble from facial hair makes it a completely different experience even though a tongue is a tongue. He pushed his tongue up inside me. I love that feeling, I just wish men had longer tongues.

"Yes, make me cum," I said. "I'm not going to let you fuck me until you've got me off."

I moved my hips back a little so his tongue was on my clit. No matter how much I love the feeling of a tongue swirling around in my cunt, it won't make me cum. Whereas I can almost not avoid it when my clit is softly rubbed.

"Yeah, just there. Not so rough. Perfect. Keep going."

I was getting close already.

"Don't stop, I'm close. A little faster. Clever boy. Nggh, yes, oh shit." I was all I could do to keep my hips still over his mouth, although experience had taught me that if I started moving too much, his tongue would lose contact with my clit and my orgasm might stop dead.

I lifted myself off his face and moved down his body. I lowered myself onto his almost hard cock. I started to stroke him with my pussy. He wasn't inside me, but my lips, wet with his saliva and my juices slide easily up and down. I moved forward a little more and then when I pushed back I changed the angle of my body a little so he slid inside. He let out a long groan as I slowly pushed back gradually sliding his entire length inside me in a single long slow stroke.

"Oh Jill, it feels wonderful to finally be inside you."

"It feels good to me too. Are you ready to cum for your owner?"

"I certainly am."

"Cum for me then."

I started to thrust my hips back and forth really fast. I knew he wouldn't be able to last long and he didn't.

"I'm going to cum," he gasped and a moment later I felt his cock twitch, felt the change inside me as his cum mixed into my own juices. I could feel it seeping out of me around the shaft of his cock as I pumped him until I got the last drop out of him.

We got under the covers and wrapped our arms around each other.

"You can kiss me now," I said.

We kissed, our tongues playing gently with each other. Gradually our kisses got slower and slower and we just lay there, our lips touching. Soon we were asleep.

In the morning I let him fuck me. Very straightforward. I lay on my back. He entered me, I didn't cum, he did. I guess it was probably how most sex with his girlfriends had been. But I was happy, there was going to be plenty of time for stronger stuff over the weekend, and it was a nice way to wake up before going downstairs for breakfast.

I dressed differently from the day before. Jeans so tight they looked sprayed-on. A V-necked top that was tight but also left a nice band of flesh above the waistband of my jeans, as well as showing off the tops of my breasts. Heels higher than the day before. I knew I looked good dressed like that and I could feel eyes on me as we walked into breakfast.

"We're going shopping," I told him during breakfast.

"Where?"

"You'll see."

I took him to one of the city's most famous sex-shops and we bought a lot of things. A paddle, some cuffs, some straps, a collar, a butt-plug, some handcuffs, a blindfold, a gag, some lube. Of course I made him pay, partially because the deal was that he would pay any expenses, and partially just so he felt even more owned. I wasn't even sure I'd make use of all of it, but it was good to have choices.

I didn't dare put the plug in his ass in the shop after my experience with Rebecca earlier, especially as he wasn't wearing a skirt and no panties so it would be all-but impossible anyway. However, I did make him put the collar on. It didn't feel enough of a symbol of ownership to have my phone-number written on his cock, I wanted something more obvious, something that would turn heads a little. The collar was rough leather with a plate on the front. It had a tiny padlock at the back. I did it up and kept the key. Only I could remove it. But I didn't plan on doing that until I left him on Sunday night or Monday morning.

Next we went to an engraver. I took the collar off him and had the plate on the front engraved. On the top line, "owned". On the second line "Jill". I thought of putting my phone number again but here, where it was visible, my name seemed a safer choice. I wasn't sure where we might end up that weekend and I didn't want too many people knowing my number. I put the collar back on and did up the padlock. I put the key in my purse.

We went back to the hotel and dropped of our purchases. And then...we went sightseeing. I figured he couldn't come to San Francisco and not ride a cable car, visit Chinatown and all that tourist stuff. Plus, it would make the contrast with all the sex stuff I would do with him later more intense. Of course he was wearing his collar in public, so even riding a cable car had a sexual aspect to it that it would not normally have.

Rebecca had texted me the address of a club in North Beach. Apparently it was the one that she and Cameron had been taken to where all the usual rules didn't seem to apply. She said there were two black twins who would be keeping an eye out for us. How she had their number I have no idea. I'd heard the story of the twins licking them with an audience so perhaps they also gave them their numbers afterwards. Just like I'm sure everyone else did, I wondered whether identical twin women had identical pussies. And whether I'd get to see.

I took Jason for dinner to a French restaurant where we had made reservations before all the plans changed. Then to Smugglers Cove for a couple of cocktails. By then it was late enough to go to the club. We got a car over. Jason seemed suspicious when we went down a dark alley that appeared to have nothing down it. To be honest, so was I, but it was exactly where Rebecca had told me. There was an unmarked door and a bouncer. He opened the door and we went in.

It was just as Rebecca had described. There were lots of tables with girls. There were men being sucked off in public. There were strippers on stage. There were bottles of vodka and scotch everywhere. I recognized a couple of Hollywood stars and a couple of local politicians.

A hostess, dressed only in tight shorts, showed us to a table and without us saying anything a bottle of vodka appeared. I poured some into each of two glasses and added some tonic. Jason's eyes were popping out of his head. I was trying to pretend I went to clubs like this regularly. Suddenly the two black twins appeared. They poured two more vodka tonics. I suspected they would hardly touch theirs but I was sure they were encouraged to use up the vodka as quickly as possible so we might need another bottle.

The twins were hot. But more surprisingly, they were stark naked. They sat down opposite us, sipped on their drinks and let their legs casually fall open a little as if they absent-mindedly had forgotten to cross them. I'd never seen a black girl's pussy before so it was hard not to stare.

I glanced at Jason. He was spellbound looking at the twins, no inhibitions about staring. I looked down. He was hard. I reached over and rubbed his cock through his pants. The twins took the cue. In a moment the two of them were kneeling in front of Jason. A moment later one of the twins had his cock in her mouth while the other was stroking his shaft. After a time they swapped over, and the other twin took his cock in her mouth. The other twin stroked Jason's balls.

I slid my hand into Jason's shirt and started to rub his nipples. I once had a boyfriend who complained that girls never paid enough attention to men's nipples. His were very sensitive. If he was close, all I had to do was rub his nipples hard and he'd cum on the spot. It's a lesson I've never forgotten.

Jason was sighing with pleasure as the two girls attacked his cock. I knew he wouldn't last all that long.

"Slow down a little," I said quietly to the girls. I wanted Jason to savor the pleasure like a fine scotch. Not do the equivalent of tequila shots.

Suddenly one of the girls moved in front of me. I stood up. She unbuttoned my jeans and pulled them down along with my panties. My legs just fell apart as if under remote control. While her sister sucked Jason, she started to lick my pussy. She knew exactly how to lick, better even than Rebecca, and she was really good. In no time she had me moaning uncontrollably. Then the two twins swapped positions. Since I couldn't tell them apart it didn't make much difference to me although I guess they both wanted a taste of each of us. We got a little audience. Women were clearly unusual in the club, apart from the strippers obviously. Female customers. It was more the kind of place that married men came without their wives or even their mistresses.

I knew Jason was close to cumming and the twins did too. The one licking me moved back to him and opened her mouth. Her sister stroked his cock until his cock jerked and a rope of white cum shot into the first twins mouth. The two of them pumped him and her mouth started to fill up. Then he sister put her head over his knob and kept it there as the final dribbles spurted out.

Then both sisters gave me their undivided attention while Jason watched. One was between my legs, the other pushed up my top and pushed my bra up too. She took a nipple into her mouth. I wouldn't last long either. A moment later I felt the familiar upwelling inside me and then I was cumming hard, my body shivering with excitement as I flooded with lovely feelings of ecstasy.

By the time my brain was working again the two black girls were casually sitting down opposite us again, sipping their drinks. Jason had done up his clothes. I pulled down my bra and my top. Then I pulled up my panties and my jeans.

We stayed some time longer, enjoying our drinks, watching the show on stage and chatting to the naked black twins as if it happened every day. But I decided we shouldn't stay too late. Although he didn't know it, Jason had to be up early the next morning. They brought Jason a bill and he paid it. I didn't see how big it was, but I assume it was enormous. He opened his wallet and gave each of the twins a $100 tip.

Back at the hotel we simply showered and went to bed. I think we were both exhausted by the activities of the day.

In the morning, I woke Jason. "We need to get up," I said.

"Why?"

"Because I'm sending you."

"Sending me where?"

"To Edith. She's getting divorced. So she's not getting any sex. She needs servicing. You will service her. You'll go there. You'll fuck her. You'll lick her. You'll give her lots of lovely orgasms. Then you'll come back here for lunch."

We got up, got dressed and went downstairs. I typed Edith's address into my phone. Minutes later an Uber appeared and Jason got in. He would be at Edith's house in half-an-hour or so. I assume Rebecca had set it all up with her, since otherwise her son might be there.

"She'll give you breakfast," I said. "See you at lunchtime. You can tell me all about it."

I wandered into the hotel restaurant and got some breakfast of my own. I started planning what I would do with Jason that afternoon with all the sex-toys we had bought the morning before. My phone beeped with the Uber bill so I knew he'd arrived.

Later I went back up to our room, had a shower, and put on a bathrobe. Just before lunch Jason returned.

"What happened?" I asked.

"I arrived. As you said, she gave me breakfast. She made me poached eggs on toast. She makes good coffee too. All she was wearing was a pinafore apron. It hid her breasts and her pussy but from behind it hid nothing. She has a nice ass."

"She has a nice body, period."

"Yes. Well, she's not as hot as you but maybe more approachable."

I laughed. "I'm not approachable?"

"I've never been with anyone as hot as you. You are my owner and you behave that way. She felt more like my girlfriend. She sucked me but didn't make me cum. Then she lay back with her legs spread and we had straightforward sex, missionary at first. She rubbed her own clit as I fucked her and she had an orgasm. We changed positions a few times. When it was time for me to cum she finished me in her mouth."

"Did you lick her?"

"Of course, you told me I had to."

I laughed. "You're learning quickly."

"So I licked her and she came. Twice I think. Hard to be sure the second time, it wasn't a big one. I noticed she has the same number on her pussy as you do."

"Yes. Rebecca owns her too. Did you do her in the ass?"

"No. Was I meant to? You didn't tell me to."

"It's fine. If she'd wanted it, she'd have told you."

"Then she told me she had to go and pick up her son so I had to go. I'd no idea she even had a son. I thanked her and she told me that I didn't thank her, I had to thank Rebecca since she is her owner. She gave Edith to me."

"Yes, that's how it works," I said. "If you want you can text Rebecca to thank her."

"What's her number?"

I opened the bathrobe. He picked up his phone and put in the number from my pussy. Then he typed a short thank-you note and sent it.

"Are you hungry?" I asked

"Not especially."

"Good. Then you can do me in the ass right now. It's time you experienced it."

I stood up, slipped the robe off completely and lay down naked on the bed. I rolled onto my front.

"Get some of that lube off the dresser. Use you finger to work some into my asshole. And rub some on your cock. Especially on the head. Then it will go in easily. Unlike the vagina, which lubricates itself, my asshole...well...doesn't. So you need to use some for anal sex. Or it will hurt the girl."

I felt his fingers probing my ass. The gel was cool and very slippery so his finger slipped in easily. I didn't need much preparation now I'd learned to relax my asshole a bit rather than my body trying to fight back.

"So just do it. Put your cock there and push. Harder than you normally push or it won't go in. But go slowly. Be firm but don't slam it in."

I felt his cock there, felt my asshole distend as he pushed, felt him slip inside. It was intense but not painful, a feeling I had already grown to love.

"You are so fucking tight," he said.

"I know. That's why anal sex is such fun for the guy. It's like doing a virgin or something."

He didn't need me to tell him what to do. He naturally started to fuck me, pulling back a little and pushing forward, each time a little deeper, the same way you sometimes have to work your way into a girl if she is not completely ready.

"Oh that feels good. Don't be too rough, it's tender back there. At least until my body relaxes completely and then you can go wild."

"You are too tight."

I laughed. "Since when was too tight a thing?"

"I won't be able to last," he said.

"That's fine. Fill my rectum with your cum."

"That sounds so dirty."

"You like dirty, don't you?"

"Mmm. I'm close."

"Sometimes anal gives me huge orgasms, but I don't think it's going to happen today. So don't wait for me. Just cum when you're ready."

"OK," he gasped. "A few more second...oh wow, can you feel it or doesn't it work like that."

"Not really. I can tell you're cumming but not from any feeling in my body. From listening to you, feeling the way you sort of lose control of your hips for a moment or two."

"What do I do now?"

"Just like with a pussy. If you want you can sort of lie there and go soft inside me. That feels pleasant and friendly. Or you can just pull out."

"I'm going to lie here for a bit then."

He slumped down with all his weight on me, pushing my breasts into the bed, his softening cock still deep in my ass. I felt my asshole closing up as his cock got smaller. It's a nice feeling. Finally he moved again and pulled out of me.

I called down and got a plate of cold cuts and cheese and a bottle of wine from room service. I put my robe back on, then went into the bathroom got the other one for him. I wasn't in the mood for getting dressed and going to the hotel restaurant. We'd have food whenever we were hungry during the afternoon.

Once room service had delivered our food, I poured us each a glass of wine.

"Get your robe off," I said.

I attached a cuff to each of his wrists and each of his ankles. I put a blindfold on him. I made him lie face down on the bed on top of a pile of pillows and used some of the straps we had bought to immobilize him. He was spreadeagled on the bed with his ass in the air.

First I took the anal plug, squirted a bit of lube on it, and worked it into his ass. He groaned as the widest part went through his asshole and then in popped into place.

I picked up the paddle. Unlike the electric cable, which made a terrifying whoosh through the air, the paddle was silent. Since he was blindfolded he had no idea what was happening. He yelped in surprise the first time I brought the paddle down on his ass. Instead of spanking him regularly with the paddle, I did it very irregularly. Since he was blindfolder, every stroke was a complete surprise burst of pain. Two quick strokes and then I went and had a sip of wine while I let the pain subside. Then three strokes and a long pause. His ass was already glowing bright red. I could sense that he was having difficulty not crying. It was painful but he was a man, and men don't cry just because their owner is spanking them.

Eventually I decided that he had taken enough. Next time maybe I'd get the cable off Rebecca. I'd never been spanked with a paddle, but I had to believe the cable was many times worse. Next time I'd make him cry.

I pulled the pillows out from underneath his body. His cock was rock hard just as I expected. I slipped underneath his body on my back, with the pillows gone there was enough slack even though he was still tied to all four corners of the bed. I maneuvered my pussy until it pressed against the head of his cock and pressed forward and up. He slid into me. It was my first time spanking someone, but apparently it was a turn-on for me too. I was really wet. I kissed him as I felt him penetrate my body.

He couldn't really move so I had to do all the work, thrusting my hips up and down his cock. It was hard work, since I had the weight of his body on me too. But it didn't take long. He let out a long groan and I felt the familiar twitch of his cock and then I knew my cunt was filling with his cream. In fact I could even feel it.

Somehow we fell asleep like that. Me on the bottom underneath him, him on top tied to the bed. When I woke up I wriggled out from underneath him and undid the straps and removed the cuffs. We rolled under the covers and continued our nap.

As originally scheduled, we went out to dinner to one of the best restaurants in the city. He wore a suit but he was also still wearing his collar. I dressed in an expensive long dress, the only one I owned. Although with the money I was earning that weekend I would be able to afford more. I realized I needed a better wardrobe if this weekend turned out to be the first of many. Plus, based on this one experience, it seemed that no matter how well-planned things were in advance, we had to be very adaptable and change things as we went along.

We got back to our room after dinner, nicely merry after a cocktail or two and splitting a bottle of wine.

"Will you be my owner again if I come back for another weekend?" he said.

"Do you want me to truly be your owner?"

"How do you mean?"

"I want you to be numbered. Total commitment."

"What do you mean? You already wrote your number on me."

"I mean tattooing it. Permanent."

"Wow. Are you serious? But it's late. Nowhere will be open."

"I expect we can organize it."

I texted Rebecca and asked her to see if the guy who numbered us all could come to our room. It was half-an-hour later he arrived with a case presumably containing his equipment. I told him what we wanted.

"I've never done that before," he said. "Will he be able to keep hard under the needle? I don't think it will work if he is soft."

I had an idea. I went to my purse and got out a small blue pill. Rebecca had got Cameron, who was a doctor, to write me a prescription.

"Take that," I said.

"What is it?"

"Viagra. It will help you stay hard while you are being tattooed. And if it isn't enough I'll suck you whenever you go soft."

It turned out that sucking wasn't required. With the Viagra and me just kissing him and stroking his nipples him he stayed hard for long enough. Finally my phone number was tattooed the length of his cock, on the front. When he was erect, no lover could miss it if she sucked him, or if he was on his back. Non-erect, in the locker room or something, it probably wouldn't show.

His cock was too sore to have sex, but I stayed the night with him even though officially the deal for an Ultimate Weekend ended at midnight. In the morning I got up early since it was Monday morning and I had to go to work. He had to go to his conference. I got the key to his collar out of my purse and undid the little padlock. It would have been fun to make him wear it to the conference but that would not be keeping him safe, as I had promised. We said our goodbyes, knowing he would soon be back.

He got his phone out of his pocket. "hi rebecca, thank you for giving me jill and the best weekend of my life"

He was the first of my girls. Except he was a boy. He would be back. I smiled to myself. Not only would he be back, he'd be paying a lot of money to be back. As Rebecca liked to say, being owned isn't always easy.

Happy New Year everyone. More stories in 2016 I'm sure. Don't forget to give feedback, authors love feedback as I keep saying (and not just me).