Gloria's Diary

Wednesday -

I woke up at Debbie's, still wrapped up in Mickey. That boy was sweet. That was the thing. He wasn't harmless, or weak, or soft, but he just tasted good. From his gaze, to his skin, to his soft hair, to that delicious dick of his, he was sweet. I couldn't get enough of him. We fucked a couple more times, then Roger had to leave, and Mickey was being nice - he left with Roger. I didn't like the fact Mickey found out about jail, but it was going to happen anyway.

Debbie and I spoke after that. Roger was an asshole, but a 9 inch dick that's hard on command is not something you play with. You grip it firmly. Roger's endowment (and his financial contributions) bought him attention every now and again. I think Debbie just liked him because he had some nerve.

I got Mickey's number, and agreed to call him. I still feel his dick now. Or I guess I should say my pussy is sore.

I went to the Y on 64th street with Debbie to work out. There were a couple of pickup games, and I've always loved the honest sweat of basketball. I could always make sense of the lines and the angles, and after thirty minutes I wasn't thinking about bills, or credit, or relationships, or jail, or anything really.

I just played good defense, made sure I was getting a sweat, and looked around me. The beauty of co-ed is that you get these young college boys. Tall, fit, and firm.

I spent most of the game marking this tall African boy, Kevin. He was dark, tall, hard as a brick to touch, and quick too. I had to box him hard, otherwise he had a decent hook shot and was dangerous when free. I know how to use my ass, and by the time I tapped his nuts a few times, we were playing a different game. He looked at me like he was surprised I knew how to hoop. I played at Texas, four years in varsity, and I just didn't graduate for my own reasons. I could ball, I knew that.

After the game I went over with Debbie to chat near the water fountain. Kevin came by with a female friend of his. Heather was her name. He didn't believe I was a nun, and I didn't press. He said he was an engineer with some phone company. So he was smart. Paid his own bills. Said he had a kid but his son didn't live in Chicago, and he was "broadly single".

So he fucked whoever he wanted, like most people. Well. I got his number. His little friend looked me up and down. I was in grey sweatpants and a grey top. Short hair, no makeup. I guess she didn't understand why Kevin checked for me.

I know something simple about men. Men want to be sure you will leave. They love to chase, love to catch, but really dread being stuck with you. They need to know you will leave. If they are sure of that, you will never have a problem with them. I never wanted to stay. I was always ready to leave, and that didn't change. Once that became clear, most men were happy with me. A lot of women say they will leave, but they don't mean it. I figure whatever most men give me I can easily get elsewhere, and I don't want to be possessed. Not by anyone. My style had worked for me so far.

I stayed once. Three years ago. I ended up with Jasmine. My lovely daughter. She was a real reminder of the true costs of a careless life. I had wanted her, she was welcome, and I loved her. She just wasn't free, and her father John was not a big part of my life, but every now and again he would show up.

After I had her I was taken care of by the Sisters of Mercy, a Catholic religious order. It was a long year, and by the end of it I figured out that nuns had free rein in the Midwest, and that I could figure out how to wear their gear. Uniforms were cheaper, more efficient, and let you think about other stuff anyway. I just never actually joined the order, but it was easy to get money from people. Shamefully the police didn't like that, and I ended up spending a few months in jail for fraud.

I hadn't been sucked that morning, so when we got to Debbie's I had a hot hot shower and had her massage my breasts. Basically breaking up the knots of milk, and helping me squeeze them out to make them more bearable. I loved having milk. It was a real turn-on being so alive in my breasts, and it turned out some men and women really loved to drink from me. I loved it.

My kid didn't even drink milk anymore, but my partners often did. They also kept my boobs firm, which mattered to me. Debbie didn't really like to drink the milk, but some men...wow...seemed like childhood never ended. She did like the stimulation. I think she just liked playing with my body. I always got wet when I expressed, but no matter. We had a deadline, and I was seeing Kevin later. I got dressed. I wore the habit this time, and then we got into Debbie's car.

Debbie dropped me off at my Mum's place, and I got to see Jasmine. She was growing. I missed her. We played for a bit, and I cried. I missed her. The thing was I wasn't really maternal. I loved her, but I felt better with her being in a safe place. The books, the school, the reading, I really didn't care for it. I never did. I still don't.

My Mum made fun of me for my nun's outfit. As she always does. We talked money, and I gave her the money I had scrambled together.

Debbie came by to pick me up to Kevin's place.

It was a North Shore high rise. Lots of windows, with a view of the lake. I know someone got fucked against those windows every now and again. Unless the windows broke. So maybe they didn't actually touch the glass. But that view was something.

He looked good dressed up, and he seemed surprised to see me in my habit. We chatted about basketball, he was a Baptist, and we talked about something else. Anything else. I asked about the young girl. She was a friend, he said, and yes she was jealous, and yes he was fucking her.

He offered me weed. I passed. I don't need excuses to get up. I don't need excuses to be happy or seek pleasure. He took a hit from the pipe, and leaned back.

He passed out. I did too. It had been a long day.

I don't know how long I was asleep, but I woke to that boy eating my pussy. My skirt was up over my chest. I started. He looked up at me, said he didn't know how to raise the point. I couldn't say anything. It didn't feel bad. He kept at it, and I stopped him. My breasts were really full. I took all my clothes off, and asked him to go get a wet hot flannel. He looked confused. He walked away.

The body on that boy. The legs, the back, the shoulders, the little waist. He was like a teak carving. Just amazing. Then he turned. His cock, I hadn't noticed before, was all magnificence and brutal glory. Thick, veiny, not too long, but substantial. If he stayed hard tonight could be good.

He brought the flannel to me. I told him if he had a thirsty mouth and strong hands, to start expressing me. I explained how it worked. He was an avid learner, and he had massive, hard hands. His strokes were long and firm, and pretty soon I was squirting milk everywhere, then he was drinking me.

He squatted next to the couch as I lay there and sucked me, his dick hanging between his legs, then sticking between them as it hardened and extended. I just needed the relief, and he sucked as If he had never breastfed as a child. When I get sucked I get wet, and really turned on. The only thing is I need a lot of pressure, and people usually suck too delicately to have an impact. Kevin was a real brute. I loved it.

He was merciless, and I came twice. Usually they sucked until they could jump on me, but this one sucked as if the breast was all he needed. When he was done I needed him in me. But he smiled, picked me up, and took me to his room. The bed in there was a huge four poster. He laid me on my back. It was plush. Comfortable. I closed my eyes for a nap.

Before I opened them, Kevin had tied up my left wrist to one corner with a silk scarf. He crossed my body, to tie my right wrist. Then my feet. I was so wet. I had no control of anything. I struggled. Motherfucker must have been a boy scout to tie so tight. There was no give. I was spread-eagled, face up, in this strange boy's bed.

His little friend walked in. Slender girl, little titties, perky though, with thick, long nipples. Fine features, hairy pussy. Naked. Long hair, in braids. She was carrying a bowl of ice. She wordlessly started rubbing ice all over my breasts. It was a lot to bear. They had just been sucked dry, and now she was playing with my nipples, my boobs, my armpits, then my pussy, then Kevin joined in.

I couldn't free myself. Then Kevin pulled out a metal plug. He warmed it with his hands, put some lube on it, and then put it in my ass. I almost blacked out. I felt full. I felt alive. I was on fire. The ice, this girls tongue, the restraint, I screamed.

This play continued, but I really needed to be fucked at this point. I was so wet. Kevin started playing with my clit with the ice. I almost burst out of my ties. It was agony. I started getting numb. Then he started sucking it hard. As soon as I was happy getting hard he would start with the ice again.

He did this 15 times. I was starting to get annoyed, when I felt his finger go into me. Slowly, slowly, he pushed it in, rubbing my g spot, torturing me, sucking my clit. Then I felt a blindfold go over my eyes. I smelt it, then my mouth was fully of pussy. Heather was smothering me with her pussy. I shoved my tongue into her. She was wet, and hairy, and fragrant.

I didn't like to eat strange women, but this felt somehow familiar, and besides, my hands were tied...She was leaning forward, playing with my breasts as I sucked her, and she started to breathe heavier. She ground against my mouth, filling my mouth with pussy. She started squirting my milk out. All over my body, and into the air.

Kevin released my left ankle. He got between my legs, and raised that ankle, kneeling between my legs, balancing my ass on his thigh. He worked the head of his cock into my engorged pussy. He was so hard. So fat. So keen. He pressed into me, and as he pushed in he released my other leg.

I tried to wrap my feet around his waist, but he held each ankle and refused. He pushed in deeper into my pussy, and then I was full of Kevin. His ropy, veiny, thick cock was stretching my pussy, with each stroke slamming its massive head into the back of my pussy.

I could feel him, but I was still overwhelmed by the pussy in my mouth, and the hands squeezing my breasts. I was gushing. He started slamming harder into me, hitting the same spot at the back. Then he moved, standing in my pussy, with his feet at the base of the bed, and using his feet to push his cock deeper into me. I shuddered, softly then harder. I grunted, tensed up, and then I came.

It was like a furnace down there, and then it exploded with each stroke. I squirted all over him. He fucked me harder, fucked me through the orgasm, and then through the second that followed it, and through the third orgasm where I started crying. I was so overwhelmed with sensation. I thought I couldn't take more.

But this bastard kept fucking me. I felt like I was going to pass out. It was incredible. I felt like I was high. I tried not to bite Heather's pussy. She bucked and came. She whimpered, and her pressure on my nipples eased. She got off my face.

I could see Kevin then, holding my ankles up, putting pressure on me, fucking me wet and then dry and then wet again. I saw him inhale, trying not to come, and then I saw him give up, and release a shower of come into me. I could feel the hot blasts of semen fill my pussy. He seemed to get bigger and harder with each blast.

When he was finished he kissed me. He was such gentle kisser for being such a heartless fuck. He stroked my hair, and kissed my neck, my shoulders, my breasts.

I saw Heather walk in again with more ice. I wasn't sure what she wanted to do with it. Kevin beckoned her to come over. She started sucking the come out of my pussy. Gently, then really sucking it. When I was clean she started sucking Kevin's dick. For such a small girl her throat could take it deep.

She pulled on his cock, and sucked hard. She gagged a bit, but didn't hesitate. His eyes were closed, but I got the sense he just wanted to fuck her to make peace. She knelt down in front of me, and started sucking on my clit again. I was raw and sore, but it felt so good.

Kevin got behind her, and pushed into her. He didn't go that far before I could feel her almost bite me. Then he started to really fuck her. Slowly. Then she started fucking him back. Slowly. Then he held her hips, and searched for a spot. I could feel when he got it because she got off my pussy and gasped. He went back to that spot, and fucked her.

I wondered what my face looked like when I was taking it deep. She closed her eyes, and tried to fuck him back. Then he got harder, and she tried, then she gave up, and let him hold her waist. He didn't seem to care if she got off or not. He was like a freight train, but then she tensed up and whimpered again. As if it was fire, she jumped off his dick, leaving it swollen, wet and waving in the air. He laughed and said something about her not being able to handle him.

He moved down to me again, and pushed into my pussy. It was welcome. I was ready. It was a real quickie, and in a couple of minutes I felt that blast of semen again, and we got to kiss again. Finally he untied me.

I could see the dawn come in. We had fucked for a while. We all collapsed on to each other.

I had to see Tony later on today. I looked forward to that. First a little nap, then a trip over to his place. I looked at my phone. Both Debbie and Mickey had called me.

Tony was a real boss. Tall, hot, rich, broad shoulders, six pack stomach, deep voice. He ran a liquor distribution business all around the south side, and also owned a bunch of commercial real estate. It kept him busy, and it kept him in cash.

He took me around his locations. I kept quiet, and looked. His staff were surprised he was with a black nun, but no one said anything. He didn't call me Sister Gloria, he just called me Gloria. It was fine. He explained he needed someone to run errands for him. I didn't understand why it couldn't be just anyone, and he kept talking about trust and how he felt good about me.

We broke off for lunch. We went to Navy Pier, and got on a boat. Apparently there are these boats which are restaurants, and serve meals to guests while going around the lake. The view was nice, it was a sunny day, and it was good to just do something different for a change.

Tony wouldn't stop with the questions. Who was Debbie? Who was Kevin? Did I fuck them? Did I ever go to church? What would it take for me to be satisfied? What did success mean to me? What did I want out of life? I was tired. I needed money, liked getting fucked, and didn't mind pussy. I was getting full, and I realized he wasn't planning to fuck me in the near future.

The pressure in my breasts was distracting me and making me bitchy. I needed to be sucked.

I started looking around the restaurant. Waiters were usually good for eye contact. I caught a customer instead. Young guy, athletic looking, having lunch with who I assumed was his dad.

Blonde, perfect teeth, but a steady gaze. I looked at him and then at the restrooms. He followed my gaze and smiled. I excused myself, and went over there. In two minutes he showed up. Apparently he had been hoping I would look up.

Peter was a senior at Northwestern, and his family knew the owner of this boat. He also had access to an office further along down the corridor. Maybe he had done this before...

As he locked the door I took my clothes off. I didn't want to be too obvious. He was a big kisser, and I had to stop him. I needed relief, and I needed it now. I pinched my nipple and smiled at him. He stopped, looked at the budding droplets of milk, and got in.

He laid me over the table, and started suckling me. He was soft at first, but with some encouragement, he got harder, and then harder, and then he had to cover my mouth with his hand. He finished left breast and then right, and then came back to the left to make sure the milk was gone and the tension was released.

My fog cleared, and I looked at him again. Handsome boy, hairy, tall, muscular, and with a thick, hairy, blonde cock. He was hard, and dripping precum. I knelt before him, and sucked. He was delicious and got harder as I sucked him. It wasn't enough for either of us, and before I knew what was happening he was behind me, I was spread over the table, and I was full of cock.

We had no time, and the beauty of this office was that unlike the toilet, no one could come in and bother us. He fucked me hard. He covered my mouth and I bit him. It made him fuck me even harder. He was a young athletic boy, and had the stamina to match.

I had to fuck him back a bit, backing into his cock to speed things up, as I was starting to enjoy it all too much. I only came once, but it was satisfying, and pulled me out of my funk. I was starting to calm down. Then he started speeding up, and I could feel his cock expand in my cunt. He fucked like a man possessed, passionately and urgently, but his strokes landed in the same place, just like I needed it.

His seed blasted out strong and hard, spurting into my pussy. He slumped over me for a second and we both caught our breath. He stood up. We exchanged numbers, and he pointed out that he had never fucked a nun before. I laughed, and we returned to the cabin. I let him out first, and then went later.

Tony was on the phone, and when he got done he ordered dessert. Chocolate cake for him, cookies for me. I was a bit hungry after the time back there. We finally talked about the job.

He wanted me to act as a kind of messenger. He had a lot of collection trouble, and he wanted me to go to people as his last option before violence. In his words, I was to "do whatever the fuck I had to do to make them cooperate". It was not complex he said, but it was hard. Some of these people were really slippery characters, and I would need to be thoughtful. He liked me because he didn't believe I would steal money.

The test visit was to "a real dick who owns a gym in an office property of mine. He's Italian, thinks he's a mobster, and has a shaky memory when it comes to my rent.". As we got back to Navy Pier I took off. My cab dropped me off at the office.

"So you're Tony's messenger bitch. How can you be a fucking nun and work for Tony?"

"That's a great question, Geno. He says you owe him fifty k. "

"Well I owe him some money..."

I said nothing

"Sit down, have a drink."

"Water please."

He was tall, dark and muscular, and as he walked away I sized him. He had a long stride and loose hips, like a man who worked with his body. His hands had been manicured but firm. He wore a white t shirt and jeans, but his watch was good platinum - Audemars Piguet, and he had the air of man who was used to being obeyed. If I could figure this out how could Tony not?

What was the point of this? We assessed each other. He had a glass of wine, and I drank my water. He looked me up and down.

"You don't look like a nun. You look too wise."

"Are you saying nuns are stupid?"

"I'm saying they aren't worldly."

"Who says I'm worldly?"

"I do."

"How are you going to convince yourself?"

In a flash Geno was next to me. He didn't say anything, he just sat, with his hip touching mine. The electricity was something. I could smell his cologne, and his morning cigar. I breathed slowly. So did he. He turned slowly and looked at me. I did the same. Pretty soon we were looking into each other's eyes.

His eyes were blue. Deep blue. With the dark brown, almost black hair it was really a lot to hold off, and pretty soon I failed. He touched my nose, then my cheek, then he held my chin. I felt butterflies in my stomach. It was like he could see me.