It was possibly my last night on Earth. I spent it with the sexiest woman I’ve ever met and still I hadn’t slept with her. What the fuck was wrong with me? I’d had her tits in my mouth and her ass in my hands. She’d come on me, yet I hadn’t fucked her.

When I saw her breasts, I thought I would die. I managed two strip clubs and had been with more women than I could even count, but hers were perfection. They weren’t huge, filled with silicone, they were real, and got me harder than any set of tits ever had before.

When she’d been on top of me, grinding on my cock, I swore my cock was going to rip his way out of my pants. And when she arched her back and came I lost it. This wasn’t a typical problem for me. During sex, I never came prematurely and I have never come in my pants unless you count the time I was 12 and had a wet dream about this lifeguard I’d seen the beach. Yet there I was, with Annalisa grinding on my cock, coming from my mouth on her tits, totally out of control. I had tried to control it, but before I knew it, I was grunting as I came in my pants.

Earlier, I thought it would be embarrassing to jerk off, now I wished I had. It would have been much less embarrassing than what I was going to face in the morning when one of those assholes came to give me my breakfast. I assumed Annalisa had noticed, but she hadn’t said anything. I suppose it was possible she didn’t know.

I’d wanted to feel her pussy, to feel her wetness, but when I’d put my fingers in the waistband of her pants, she’d bolted. I suppose I was moving too fast, but for a guy like me, there was only one speed. I wasn’t one of those wine and dine guys. I was used to opening my fly and saying “Suck it” or “Bend over” and getting exactly what I needed. With Annalisa, it was different, and I should have known that. I had no clue as to how many men she’d been with before, but I was pretty sure she wasn’t a fuck on the first or second date kinda girl.

I could have easily let it go. There was an actual chance that I’d make it out of my situation alive. They hadn’t killed me and they’d had me two days. That was a good sign. Once out, I could fuck anyone I wanted. The problem was now that I’d met her, she was the one I wanted to fuck. I was a competitive guy, I wanted things I couldn’t have. I’d set my mind on banging the only daughter of my enemy, Franco Morelli.

The part of me that protested, saying that Annalisa was a sweet person, a kind woman who was sexy as fuck lost out to the bravado voice. I needed to convince myself she was just a conquest, something to stick my flag in, because everyone knew that if you let a woman get too close to you, it could fuck with your head.

I closed my eyes and tried to let sleep take me. I had so much on my mind. My father, and whether or not he’d make the deal with Franco, my shoulder which still hurt, my pants, which were wet and sticky, and Annalisa. Annalisa won out. Recollections of her sweet kisses had me calm and relaxed. I drifted off to sleep with visions of her on my mind.

In the morning, I woke stiff, sore and not well rested at all. I had a hard time sleeping, partly because I couldn’t sleep on my stomach like I liked to because of my the way my wrist was cuffed to the bed but also because I couldn’t get Annalisa out of my head. I’d had a few wonderful dreams of her. I’d taken her to dinner, we’d gone walking in the park and then I’d made love to her in my room. It was an odd dream because I’d never taken a girl to my house. I chuckled. I sure as fuck couldn’t take Annalisa to my house. I couldn’t even imagine what my parents would say if they saw me walk through the door with her. My dad might be proud if he thought I was banging Franco’s daughter, but not if it had been anything more like in my dreams.

I had a nightmare about Annalisa too. She’d come down and had been about to fuck me when her father came in. At first, I’d been afraid for her. In my dream I’d looked at her face, worried about what he’d do, but she’d burst out laughing. “You really think that I’m this sweet innocent girl?” she taunted. “I was just fucking with you. It’s the best kind of torture.”

I tried to shake the bad feeling as I lay in bed. I focused more on what I had to do to get out of here. I no longer wanted a quick and painless death. Sure, if it came to that, I’d be grateful, but I wasn’t giving up just yet. I also had my bladder to focus on. Once again, I had to take a wicked piss.

I was taken from my thoughts by the sound of the keypad. The door opened and it was Vito. He was the enforcer for Franco. I rarely saw him alone.

He walked into the room with a tray of food. It was pancakes and smelled fucking delicious. He set it on the dresser near the door and tossed me a set of keys. “Use the bathroom and take a shower. You fucking stink.”

“Good morning,” I said in snarky response. “The breakfast smells delicious. Give my compliments to the chef.”

He just glared at me and grunted. “Cocky little shit,” before leaving me alone in the room.

After uncuffing my wrist, I went to the bathroom to relieve myself. I had to admit, it was nice to have a real toilet. I was torn between eating and showering. The food smelled great and I was starving, but the fact that I’d had to peel my boxers from my body because they were stuck to me made the shower win out.

I stripped down and stepped into the shower. Part of me had expected it to only have cold water, which I would have been fine with, given the situation, but it was warm and felt great on my shoulder.

I washed myself and then brought the boxers and sweatpants in with me. I’d rather walk around the room nude than put those crusty things on again. I washed them and hung them over the shower curtain bar to dry.

I was proud of my body, and I had no problems walking around my room nude. It turns out I didn’t have to. When I got out of the bathroom, there was a set of clothes on the bed along with a few magazines and a newspaper. I pulled the t shirt over my head then put on the boxers and sweats.

I sat down on the edge of the bed to eat the breakfast. Though the pancakes weren’t hot, they still tasted incredible. I ate as I read the newspaper. It reminded me of my dad. He read an old school paper one every morning. I’d teased him about getting a tablet to read like the rest of the world, but he’d said that sometimes change wasn’t good. I wasn’t sure if I agreed, but I was glad I could at least catch up on events.

Vito hadn’t told me to re cuff myself at any specific point, so I just walked around the room stretching my legs. I tried to work out, missing the feeling, but my shoulder prevented this. I did try to move it a bit, to get range of motion back.

Hours had passed until I heard the sound of metal scraping metal. I looked up at the door to my room to see a small slit now opened. I’d noticed it before, but knew it was too small to even get my hand through. I saw a set of eyes.

“Go cuff yourself.”

I thought about telling whoever it was to go fuck himself, or to come in and make me, but the reality was that things were going pretty well for me, all things considering, and I didn’t want to lose the privilege of using the bathroom. I walked to the bed and put the cuff on my wrist. It hurt as I’d already rubbed my wrist raw.

“Toss the keys toward the door,” the voice said again.

I thought it was Marco. Once I’d tossed the keys toward the door, I heard the code being entered and the door opened. Marco walked through it.

“I thought it was you,” I said giving him a smirk. “I recognized your sexy eyes.”

I thought it would have pissed him off but he let out a laugh. “You’re a sick fucker,” he said. “Fucking comedian with a death wish.” He walked over to me and looked down at my shoulder. “Wanna know what’s funny?” he asked, removing the bandage and looking at it more closely. “My girl just said I had sexy eyes this morning. I’m gonna have to tell her that she has competition.”

I grimaced as he pushed on my wound a bit. “Competition usually makes women try harder,” I said through gritted teeth. “You can thank me later for getting you the best blow job of your life.”

“She already gives the best blow jobs I’ve ever had.”

“Ever have Jenny from Bobalones suck your cock?”

“Can’t say I have. What she got fold back teeth or something?” he asked, starting to put a new bandage on it.

I laughed. “Naw, but she sucks so hard that you swear she’s gonna suck your balls out through your cock.”

Marco shook his head laughing. “Not really a mental image I wanted.”

“You know you love it,” I teased.

He just laughed.

It was a fucking shame that Marco worked for the douche bag. He’d have been a great guy to have on my team. I’d thought it before, and I was sure now. I bet he and I would have become great friends.

Marco was quiet as he finished. He stood and walked to the door. “Once I go, you can take the cuff off, so you can use the bathroom and shit. Lunch is just a sandwich and chips. Vito gave your compliments to the chef this morning, but sadly, she’s out shopping and couldn’t make you lunch. You have to suffer with man food.”

“Did you at least cut the sandwich into little triangles?” I asked, giving him my smirk.

“Yep, crust off too.”

I knew he was fucking with me, and he earned a smile and a laugh.

He tossed the keys to me then turned to leave.

“Hey Warden,” I called out.

He turned back around.

“Thanks for the magazines and the newspaper. I’m going crazy in here. Any chance I can get a TV, computer and a clock. I never have any idea what fucking time it is. I don’t even know if it’s day or night.”

“I’ll check with guest services,” he answered with an eye roll, then turned and left.

Once he was gone, I removed my cuff. It would do my wrist good if I could keep it off for a while. I read through the magazines, though I didn’t have much interest in Guns and Ammo. It was at least something to do.

I decided to take a nap while my cuff was off. I hadn’t slept well since being here, and even though my shoulder still hurt like a mother fucker, I was able to get more sleep on my stomach.

I have no clue how long I slept, but I woke to the sound of the metal peep hole being opened again. I saw Marco’s eyes.

“Cuff on again.”

I rolled over and attached it to my wrist. I heard the familiar beeping and the door open. “Come back to discuss quality blow jobs?” I asked laughing.

Marco didn’t return my laugh. In fact, his eyes went wide and he shot me a look.

I was about to ask him what his fucking problem was when I noticed he wasn’t alone. He walked into the room followed by Annalisa. Her cheeks were pink. Marco was carrying my dinner tray. She was carrying a small brown leather bag.

I looked at Marco with raised eyes. My usual self would have asked if he was bringing me a conjugal visit, but it was far too close to the truth to joke.

He set the tray down and walked over to me. “So earlier, when I looked at your shoulder, I noticed it was puffy. I pressed on it, and it looked infected. I brought someone with some medical training.” I noticed that he never said her name, nor that she was Franco’s daughter.

“We met the other night,” Annalisa said.

My jaw dropped. Had my dream been right? Did everyone know what she was doing with me? Was it all a fucking game?

“Oh, that’s right. You brought him dinner the night his father shot up a restaurant full of innocent people.”

I saw a look cross Annalisa’s face, as if she was recalling what an awful person I was. I didn’t like that Marco had put it there, but he hadn’t been lying. I’d read the paper. It was buried on the 8th page, but it said that the people were recovering from the drive by shooting at the restaurant and that the police had no suspects.

“Can I look at his arm?” Annalisa asked, not mentioning anything more about us knowing each other.

Once again, I had the opportunity to throw what she and I had done in his face, but I kept quiet. I told myself that I was waiting for the time that would give me the biggest bang. I definitely wanted to do it when Franco was in the room. “If you do it,” the little voice inside of me said.

It wouldn’t make much of a difference to Marco, I argued back. It would embarrass Annalisa, and probably shock Marco, but he had his girl, the one he said gave amazing blow jobs. He’d been embarrassed when I’d mentioned it in front of Annalisa. A light bulb went on. Was it her? He’d never said her name. For some reason, jealousy washed through me. I’d never given a fuck if any girl I’d been with had been with another guy before or after me, but for some reason, the idea of Annalisa sucking Marco’s dick really bothered me.

Annalisa moved to the side of my bed and started removing the bandages. “So, you two are a couple?” I tried to ask casually.

Annalisa stared at me with wide eyes. Had I figured it out? Was it secret? Maybe I wasn’t the only guy whose room she snuck into at night.

“Us?” Marco laughed. “Yeah, right. She’s like my sister.”

I saw Annalisa’s cheeks flush.

“Hey, down south…”

“Annalisa, you have my permission to hurt him. I’m from the south,” Marco suggested.

He knew I was joking, but there was a bit of me that still wondered about the two of them. It bothered me that it bothered me.

“It’s infected,” Annalisa said, more to Marco than me. “I can clean it, but he might need antibiotics. What’s he on for pain.”

“Nothing,” Marco and I said at the same time.

“Are you serious? He’s been fucking shot!”

It was the first time I’d heard her swear. She reached into her bag and got out some red pills. “These will help with the pain. I’ll have to get you an antibiotic. I can’t write prescriptions. I’m not actually a doctor.” She sounded like she was apologizing. “I’m in school, but—”

“I can get that. Tell me what you need.” Marco cut her off.

I wasn’t sure if he didn’t want her talking to me or if he had something to say.

Annalisa went to work cleaning it. It was much more thorough and much more painful than when Marco had done it. I moaned a lot and even cried out once. “MOTHER FUCKER!” I shouted when she poured something on it.

“Should have you down here for questioning,” Marco teased.

Clearly, Annalisa didn’t think it was funny. “I’m trying to make him better, not worse,” she said. “Maybe if you’d have cleaned it…”

I admired how she stood up to him.

“I did clean it,” he said. His phone went off and then again. It went off a third time. “Almost done?” he asked, looking at his phone.

“Got some other fucker to watch get tortured?” I grimaced.

“Ha, no. You’re my entertainment tonight.”

“I’m doing the best I can,” Annalisa said concentrating on my shoulder. She was bandaging it again. “Yeah, you can tell her you’ll be up soon.”

“Oh!” I exclaimed another light bulb going off. Annalisa must have thought that it was something she did because she stopped for a moment. “Your girlfriend is texting you, you know, Hoover.”

Annalisa raised her eyebrows and Marco shot me a dirty look.

“You can go now if you want,” she said.

Marco looked shocked. “Hell, no. I’m not leaving you alone with him.”

I was about to ask why the fuck not, but Annalisa spoke first, “Why the hell not? He’s cuffed. What can he do?”

“A lot,” Marco said. “He’s got quite the reputation.”

I started to get even angrier, but Marco spoke again, “Then again, I think it might all just be a bullshit cover.”

Annalisa and I both looked at him.

“He’s come onto me like three times. Even just today, he told me that I have sexy eyes.”

I closed my eyes and groaned but Annalisa laughed. “Is that so? Well, he’s right. You do have sexy eyes...I mean, not quite as sexy as Dante’s.”

Her words had my full attention. I looked over at her, my gaze locking with hers. We shared a moment.

“And that’s why I’m not leaving you alone with him!” Marco laughed.

“I’m just about finished anyway,” Annalisa said, putting a piece of white tape over the gauze. She stood up. “That should be a bit better.”

“Enjoy dinner,” Marco said, walking to the door.

“I hate to see you go, but I love to watch you leave,” I teased. I’d been watching Annalisa’s ass.

Of course, Marco thought I meant him in a joking way again. At the door, Marco turned around and tossed me the keys again. “Get some rest. You look like shit and your jokes suck.”

The two of them left and I had to wonder if Annalisa would be back. Not even thirty seconds had passed and the door opened again. I’d already had my cuff off.

“Don’t say I never got you anything,” Marco said from the door tossing me a watch. He was gone again.

It might have seemed like nothing, but knowing what time it was, was a big deal. Now I could know for sure how many hours and days had passed. I also was aware that it was 7:30. I’d thought it was much later.

I’d masturbated to the thoughts of her from the night before and as ironic as it was, the feel of her fingers on my skin as she cleaned my shoulder. It wasn’t that I wanted to masturbate, but I didn’t want to come in my pants again. By ten, I wondered if she was coming, and by eleven I was pretty sure she wasn’t. At midnight, I decided to fall asleep. I’d read the magazines twice and couldn’t stay awake much more. It was the first time, I could ever remember, that a woman had turned me down for sex. I couldn’t blame her though. Annalisa didn’t seem like the one night stand kind of girl.

It was ten after twelve when I heard her at the door.

She slid open the peep hole, the way Marco had done. I saw her peek in. Her eyes were way the fuck sexier than his. I wasn’t sure if she was looking to see if I was cuffed. I didn’t want her to go, so I reached over and cuffed my wrist then tossed the keys toward the door.

She pushed the buttons on the pad and opened the door.

My jaw dropped when I saw her. She was wearing a pale pink silky robe that went to her mid thigh. I hoped she was nude under it and I planned to find out. Her hair fell loose and wild. I could tell she was wearing makeup, though it didn’t look overdone.

She stopped just inside the door and bit her lip. Her demeanor and her clothing, or lack of, told me she’d decided to take me up on my offer. We were going to have sex.

“I wanted to check on your shoulder again,” she said nervously. We both knew that wasn’t true. She still stood at the door. “I um—I’m not usually like this. I just wanted you to know.” She was either an amazing actress or she was nervous as fuck.

“I know you’re not.” Did she think that I thought her a slut? She was far from that and I could tell. I didn’t date, but in her case, I might have made an exception. I wanted her to know this. “I want you to know that if I were able, I would have taken you out to dinner and someplace very nice after. I would have bought you flowers and treated you how you deserve.” I pulled on my cuff. “And I sure as hell would have been able to use both hands.”

All of it was true. I would have treated her like a lady. The first lady I’d dated. It was also true about the cuff. I wasn’t even sure how I was going to have sex with it on. I had to just lie there on my back.

Annalisa backed up and picked up the keys that were laying at her feet.

“Oh baby, please tell me you are going to uncuff me.”

She looked at me warily.

“I promise I won’t try to leave. I know it would get you in trouble. I just want to be able to be with you the way you deserve.” I hated to put her in this position, and the truth was, I’d run if I thought I could get away. I wanted to fuck her more than any woman in my life, but it was my life we were talking about.

“Good. You wouldn’t get far anyway. There are guards all around the house and upstairs. It was hard enough for me to sneak down here, and I’m allowed everywhere. I don’t want you to get hurt. I still hope you can get out of here you know.”

I could tell she was being sincere, but she must have known little of her father’s business. Even as good as things were going, I knew it was less than a 50% chance that I’d make it out of this house alive, and that was probably being generous with the odds. I knew my father would have to agree, which was a longshot, and then, these fuckers would have to hold up their end of the bargain, which was an even longer shot.

She was right though. I wouldn’t make it out without plan. I had no idea where I was or even how to get out of the house, let alone to safety. If I were going to escape, I’d have to either, wait until there was a much better opportunity or someone came to get me. And I’d be lying if I said that I wanted to go before spending the night with her. I was pretty much a dead man having his last meal.

She walked to me slowly. Her hands trembled as she unlocked the cuff. She waited a moment, I guess to see if I would try to run. When I didn’t, she sighed and set the keys on the nightstand. She stood there nervously.

It turned me on like nothing else to see her trepidation. It seemed awkward with her standing and me lying in bed, so I stood slowly, hoping she didn’t think I was trying to make a run for it. I pulled her to me for a hug. It was the first time I’d had both of my arms around her. She was trembling slightly. I put my face in her hair and hugged her tightly. “You smell so good,” I moaned, holding her close. She hugged me back. It was incredible how much humans need physical contact and having her arms around me reminded me of how much I missed it.

After a long hug, I pulled back and kissed her lips softly. “I’m so glad you came,” I whispered running my hands up the back of her robe. It was so soft. “Are you wearing anything under that?”

She nodded. “Want to see?”

Anyone who tells you that the sexiest thing in the world is seeing a woman nude has never seen Annalisa Morelli in what she had on under that robe. The pale pink top, made of some sort of see through material let me see the outlines of her perfect nipples, and the bottoms, some sort of silky shorts, hid just enough to drive me wild.

Growling, I slid my hands around from her back and up under the top. I palmed her breasts causing her to arch her back, in essence offering them to me. It took less than ten seconds to have that top off and her nipple in my mouth. I thought of little else in the past twenty-four hours, yet my memory hadn’t done them justice.

I felt her sway slightly as I sucked on her perky nipple. I wasn’t too steady on my feet myself. I sat down, setting her nipple free from my mouth with a pop, before pulling her on top of me, attacking the other breast with my mouth. Annalisa straddled me as I went back and forth, sucking her pert nipples into my mouth playing with the responsive flesh with my teeth and tongue. Her hair was falling forward, tickling my face as I massaged and licked her breasts.

I loved having her on top of me with her breasts in my mouth like we’d done the first night, but my new freedom gave me the opportunity to explore her body in different positions. I rolled her onto her back and stared down at her body. She bit her lip and decided that I wanted to bite on it too. Sucking it into my mouth, we began a series of slow wet kisses. While our mouths explored each other’s, my hands explored her body. I slid my hands inside of her shorts and was surprised and pleased by the soft curls. I loved a smooth pussy, but for Annalisa, the curls just seemed to fit.

As I parted her labia with my fingers, I noticed she was holding her breath. I could feel her heartbeat, and it was going a mile a minute. I’d wondered about her level of sexual experience over the past few days. In my mind, it had ranged from her having just a few boyfriends and lovers to her being wild and just toying with me. What I found to be the truth shocked me even more than the crazy ideas I’d had.

Any doubt as to the amount of sexual experience she’d had, it was gone when I pressed my finger into her body. It was tighter than anything I’d felt in my life. As my finger moved in and out, something was in the way of me fingering her. I could push my way through it slightly, but it was definitely different. I pumped my finger in and out of her body slowly, watching her face for pleasure, but I noticed she was wincing slightly. I moved my finger again, feeling at the stretchy part of her that was keeping me out. When it occurred to me as to what it could be, I knew I gasped. One look at the blush on her cheeks and it was confirmed. The barrier that I’d been feeling made me aware that this goddess in my arms was a virgin.

At the realization that my girl was pure, several things happened in my mind at once. The man in me, the one with primal urges, wanted to change positions, spread her legs wide, and spear her with my cock, filling her with my seed. It was primal and wild, and completely irresponsible, yet it was what my body wanted to do.

The asshole in me wanted nearly the same thing, but for a different reason. When the fucker, Franco Morelli, put a bullet in my head, I wanted to be wearing his daughter’s virgin blood on my cock and throw it in his face. How I’d love to describe how tight she was and how she cried out as I fucked the innocence right out of her.

Then there was the gentleman in me, the one my mother had raised. Despite who her father was, I wanted to protect her, be sure she was safe. I didn’t want to hurt her. Much to my surprise, the gentleman in me won out. “Babygirl, you want to give this to me?” I asked, moving my finger more slowly, stroking it against her barrier.

She bit her lower lip and whispered. “Yeah. It’s no big deal. Let’s not make a big deal out of it.”

From what I knew, it was a very fucking big deal, but I wasn’t going to argue. Though the gentleman in me had won out, it hadn’t been by much. The primal man and the asshole were close contenders and I wasn’t going to spend any more time talking about it. If she was sure, it was good enough for me.

After pumping one finger in until it fit better, I added the second. Annalisa moaned in what I thought was discomfort, but when she started grinding her pussy against my hand, I added my thumb to her clit.

Her face was buried in my neck when she came undone onto my hand. “Oh, god Dante. That was—so-so…” She didn’t finish her thought, kissing me instead.

As we kissed, her hands began to roam and found my erect cock. I loved how she was taking initiative. While her fingers, rubbing it softly through the thin material of my boxers felt amazing, I wanted there to be nothing between her and it. I pulled them off and she gasped as my cock sprang free.

Her eyes were transfixed on it, while mine were on her. The sight of a woman’s hand wrapped around a man’s cock is one of the most beautiful things in the world, but Annalisa’s hand wrapped around mine had my cock weeping and me groaning. Her finger traced the head spreading around the pre cum. It clung to her fingers and my cock, making a thin clear string as she moved her finger away, only to return it and try again. I wanted to watch this forever but I also wanted my cock to feel what my fingers were feeling.

“I need to be inside of you.” My voice was gruff.

She looked up at me from my cock and smiled softly. I went to reach around her for my pants, which were on the floor next to the bed when I realized that they weren’t my pants, well at least not the ones I’d been wearing, the ones with my wallet. Without my wallet, I had no condoms.

“Fuck,” I cursed. “I don’t have any condoms Babygirl.”

She bit her lip. “It’s ok. I’m taking birth control pills.”

I’d heard that from many girls in the past and I hadn’t trusted one of them. My family had money and power and you never knew who wanted to use a baby to claw her way into the family. It would have worked too. My mother wanted a grandchild in the worst way, but between my sister, the ice princess, and me, it sure wasn’t going to happen soon.

Annalisa was different though. First of all, she wasn’t seducing me, I was seducing her. And second, she came from the same kind of family that I did. If she got pregnant, there would be hell to pay for her. Not only was I the son of her family’s arch enemy, there was a double standard for women, especially in old fashioned Italian families. If I knocked up a woman, my father would have paid to have it taken care of, or called the woman loose and maybe given her money to go away. If my sister got pregnant, I’m pretty sure my father would march whoever the guy was down the aisle, gun pointed at his back, and make him marry my sister. Neither was gonna happen though. My sister had no interest in guys and I had no desire to repopulate the earth.

I did have to admit though, when facing death, the idea that part of you will live on is a bit tempting. And as an added bonus, I’d love to look Franco Morelli in the eye before he pulled the trigger and tell him that my child was growing inside of his daughter. Either way, the point was moot, because she said she was on the pill.

It would be different for me though. I’d never come inside a woman’s pussy before without a condom. Like I said, I didn’t trust them. Mouths were a different story, as were asses. I always wore a condom for anal sex, and I loved shooting my load down a bitch’s throat but going raw inside of a pussy was going to be a first for me.

My cock swelled at the thought, and I worried I’d hurt her. Wanting to let her take control, I laid back on the bed and pulled her on top of me. She was on her knees straddling me. “Baby, we will go at your pace.” I teased my cock at her entrance sliding just the tip in. “Go as slow as you need.”

A blush crept up her body but she began lowering herself onto my cock. I have no idea how it fit or how much pain she was in because it felt like my cock was being squeezed to death. I felt the barrier and looked into my girls eyes. I’d fucked countless women. Maybe it wasn’t a different woman a night, but it was a few a week, and for how many years? I didn’t even want to do the math, but in all that time, I’d never fucked a virgin. I had no clue how to do this. Did you just do it like a band aid or was slow and steady best? I tried to hold still waiting for her to decide.

She bit her lower lip and pressed down onto me but I really didn’t budge. It felt so fucking good. I had to fight my instincts which said grab her hips and slam her all the way down burying myself in her warmth. I’d been looking into her eyes the whole time until I made the mistake of glancing between us. The way it looked, my dick with the head inside her pussy, spreading her lips wide almost had me coming right then. “Fuck Babygirl, do you know how hot you are? I want you so fucking bad.” I barely recognized my own voice, as I tried to speak through gritted teeth.

I couldn’t help my hands any longer and they went to her hips. I swear I wasn’t going to slam her down on me, maybe just move her slightly. She decided to take control and moved up and down the slightest bit then dropped down onto me. It felt like a rubber band snapping around my cock and then heaven, pure heaven as I was sheathed inside of her wetness.

“Ow.” It was just one little word, and it was all she said, but it was so fucking cute.

I swore I fell in love with her that instant, if I was the type of guy who did that.

Damn she was wet. I really wasn’t much for foreplay, but I’d have to rethink my position on it if this is what it got me. She moved ever so slightly causing me to wonder if I had died and gone to heaven already. Maybe it was hell because all I wanted to do was thrust my hips.

Her body must have craved it too, because she began to move up and down a little. My hands, which were still on her hips, helped her. Each time she moved down, I thrust up to meet her.

The feeling was incredible, and it was more than the fact that I wasn’t wearing a condom, it was that I was with her. I actually cared about her, in some form or another. I didn’t have a name for it yet.

The first time I came that night, and I say first because I came three times, was while she was still riding me. As she moved up and down on my cock, her tits bounced near my face. I couldn’t resist and while sucking on them, I filled her tight pussy with my cum. I’d felt it come from my toes. Even though I’d masturbated earlier, I think it was the most I’d ever come in my life.

I usually came inside, while wearing a condom and then tossed it. Occasionally I’d pull off the condom and come all over a woman’s back or tits so I knew about how much I came. As I came inside of Annalisa, my cum came out around my cock, pooling at the base of my shaft. I couldn’t look away It was a lot more than I usually came with other women, and I knew that there was a ton of it still inside of her. The other reason I couldn’t look away was that my come was pink. I knew that it was mixed with her blood.

“Do you hurt Babygirl?” I asked kissing her breasts as I pulled her to me so I could hold her, my cock still inside of her.

She shook her head and whispered, “No,” into my chest.

We lay like that for a while, my cock softening until she started kissing my chest, her mouth moving to my neck. I was hard within seconds and had lifted her off of me, flipping her onto her back so I could be on top.

I’d always thought fucking in the missionary position was boring, but with her legs thrown up over my shoulders and me buried deep inside her, it was anything but boring. Although I was afraid I was hurting her, I couldn’t seem to get deep enough. I thought there would be a lot of blood, but there was really very little. When my cock moved in and out of her warm body, I could see traces of it, but there was barely enough to have stained the sheet, which is a good thing, because I’m not sure how I would have explained that.

Her body fit me perfectly but I wanted more. I wanted to kiss her and touch her and be inside her all at the same time. I’d never felt this way before, and although I chalked it up to not having sex in days and the fact that I wasn’t wearing a condom, somewhere inside of me I knew it was something else.

With her hair fanned out on her pillow, her head thrown back and eyes closed, she actually looked like an angel. I’d never seen a more beautiful woman in all my life. I felt like a kid with ADD trying to take it all in. Her face, her hair, her tits bouncing with each thrust, the way the lips of her pussy swelled each time my cock drove into it. And God damn it, the way her belly button looked—because fuck me, I could see the impression of my cock pressing from the inside on her flat stomach as I moved in and out of her. That was probably what sent me over the edge causing my entire body to tense as I marked her as mine for the second time.

I couldn’t bear to remove myself from her warm body, so to prolong the sensation, I leaned down and began kissing her softly. It started out slow and gentle, but within minutes, it was feverish and I was thrusting in and out of her again. This time it was her mouth that got me. Whether it was the soft sounds she was making or the way she was kissing me I felt my balls tingle and knew I was close to a release. I tried to hold off, wanting the feeling to last, but when her tongue licked my jaw and she began to suck on my neck I had no more control and for the final time that night, I came deep inside of her.

She lay in my arms while we caught our breath. I kissed her forehead softly and she moaned.

I swore I’d check in with her, but I’d been so lost in how good she felt that I’d forgotten. She looked like she’d been enjoying it. Her hands had been on my back, scratching and massaging as I took her. “Oh shit baby, are you hurt?” I asked.

“No,” she answered softly. “I just have to go and I really don’t want to.”

“You could stay here all night,” I teased. “Would definitely surprise someone in the morning.”

She giggled. “Marco or Vito might be okay. My dad or Donnie would have your balls.”

I tensed up. Did she have a thing with that hulk of a man Donnie? And why the fuck was I jealous all of the sudden. Clearly, she hadn’t fucked him. I’d been her first. Even if she did have a thing with him, what did I care who she liked? She was just a fuck, wasn’t she? I knew the answer to that question before I’d even finished the thought. She was more, so much more than a fuck. I just couldn’t put my finger on exactly what I was feeling with her.

“Is something wrong?” She was staring at me.

I realized I’d been scowling. “Is he your boyfriend or something?”

“Who Donnie? Oh, God no. He’s like a brother to me.”

I chuckled. “You said that about Marco.”

“What can I say, my dad is overprotective. Speaking of which, I do have to go. I really can’t be seen here. I’ll get in so much trouble, and you’ll be dead.”

I didn’t want to tell her that I’d likely be dead soon anyway. Instead, I stayed in the present. I pulled her in for a hug, wanting to hold her like that all night, but knowing I couldn’t. “Tonight meant so much to me,” I whispered holding her. “Please be safe going back to your room.”

She stayed another few minutes then pulled away. She kissed me put back on her clothes and robe. She looked back over her shoulder, but said nothing when she left.

Watching her go was the hardest thing I’d done in my life. I’d been ready to die a week ago, but now—now I wanted so much to live, if for no other reason than to spend just one more night with her.