CO Leep Loses Her Anal Virginity

My cellie and I were woken up early one Thursday morning and told we had to move. Of course, neither of us was excited about that, and after a few questions, we found out that our cell was going to be painted and we would be back in a few days. It didn't take us long to pack our stuff, and we were off to our temporary cell.

As it turned out, we had temporary single cells. Once used as segregation, or "the hole," an entire pod had been converted to a short-term single-cell pod so the prison could repaint all the cells. Six other guys from our pod had come with us, making us the only eight guys in the entire pod. This was definitely going to be an interesting time. There was no doubt we would be there through the weekend, and now that we were getting settled in, I was looking forward to having a single cell for a few days.

On my second night there, I decided to stay up a little later than usual to enjoy being alone. I turned the lights off after lockdown, which was late since it was a Friday night. I found a movie with hot, young, scantily clad women then started playing with my cock, going slow since I knew I could take my time and not have to worry about being interrupted. I didn't bother covering up. It was kind of chilly but nothing uncomfortable. Most of the COs that worked the pod were female, but I didn't care. It wasn't anything they hadn't seen before.

About fifteen minutes later, I noticed a shadow walk by the door, and I didn't pay any attention to who it was. A moment later, the cell door opened. The sliding doors in this pod were a lot quieter than those in my regular pod, there was no echo through the pod, and all I heard was a barely audible click. It wasn't until the cell started to light up that I realized the door was opening. I looked over and froze with my hard cock in my hand. I didn't have a clue as to what was happening. There was a CO in the doorway motioning for the booth officer to close the door back. My eyes hadn't adjusted yet, I couldn't tell who had just come into the cell, but it was the silhouette of a woman.

"You look like you could use some company," she said, untucking her shirt and starting to unbutton it at the same time, kicking her boots off.

I instantly recognized the voice. It was Leep. She had a very distinctive high-pitched, nasally voice, which was on the verge of annoying. Leep wasn't the hottest CO at the prison, but she was easily in the top five. Her only real downfall was her nose; it was way too big for her face. She did have a nice body, at least what you could see through her manly CO uniform. I couldn't believe Leep was in my cell undressing. I just sat there holding my cock as I watched her take her pants off. "Uh, yeah," I finally replied, sitting up, "yeah, that sounds great."

As soon as the words were out, I realized how stupid I sounded. By now, Leep was standing in the middle of the cell, half-naked, staring at me. "Ok, well, I've got my whole lunch hour," she replied, taking a step toward me.

"Turn the lamp on before you come over," I told her, pointing at my reading lamp clipped above the desk.

"Why?" she asked, stepping toward the lamp and reaching out for it.

"So, I can see you better," I replied as she turned the switch, "I want to see how you look in the light. I'm going to enjoy this to the fullest."

The lamp cast a dim, yellow glow throughout the cell, just enough light to see by. Leep was now standing at the end of my bunk, she still had her shirt on, but she had unbuttoned it, revealing her bra. She was wearing a matching bra and panty set, and they mainly were lace, sky-blue in color with bright sun-yellow accents. Leep stood there for a moment, letting me take in the sight of her sexy, toned body before Leep crawled onto the bunk. She was sitting on her knees beside me, staring intently at my cock. "Keener told me you had a nice prick," she said, moving a hand to my cock and grabbing it gently, "but, damn, I thought she was exaggerating."

"Keener told you what happened, huh?" I asked, smiling.

Leep was still focused on my cock, and she was stroking it softly now with short strokes. "Yeah, that's why I'm here," she replied, moving my dick around and looking at it, "I had to see for myself, and I'm glad I did."

As soon as she was finished speaking, she leaned forward and put her mouth on my cock. It had been a long time since I'd had a blowjob, and her warm, wet lips felt amazing on the head of my prick. She had Short, dark brown hair that she always kept pulled back into a short ponytail, so there was no need for her to hold her hair, and Leep used her free hand to gently cup my balls as she slid her lips down my shaft. Her unbuttoned shirt draped around her body, hiding it down to her waist. She arched her back, and her ass stuck up in the air. I was surprised. Her unflattering uniform hid her assets very well, she had wider hips than I'd expected, and her ass was plump and full.

I reached over and put a hand on her ass. It turned out she was wearing a thong, and I grabbed all ass. I moved my hand up and hooked my thumb in the waistband of her panties. "We don't have long," I said, pulling her waistband out. "why don't you stop wasting time and take these off."

I moved my thumb, letting her waistband snap back against her creamy skin. Leep eased her mouth back up my shaft. She kept her hand on my balls and continued to slowly stroke my dick. "You don't want me to suck you off?" she asked, looking up at me confused.

"I'd rather fuck you," I told her.

"Ok," Leep replied, sitting back up on her knees.

She wasted no time hooking her thumbs in the waistband of her lacy thong and pushed them down. My attention instantly went to her crotch, and I could hardly wait to see what her pussy looked like. She closed her legs enough to let her panties fall to the bunk. I was not disappointed. Leep was shaved bald, and her fatty little labia hid her inner lips nicely. I half expected her inner lips to hang down a little as Keener's had. She moved to take her panties off, lifting her knee and spreading her legs a little. I reached over and cupped her pussy, slipping my middle fingers between her lips. She was already unbelievably wet.

Leep inhaled quietly as she freed one ankle from her twisted panties. She left them around her other leg and moved into position on my lap. I kept my fingers between her pussy lips the entire time. Once she was on my lap, I tried easing them inside her and was surprised again, this time by how tight her fuckhole was. I couldn't work my two fingers inside of her. How was she going to get my cock in her, I wondered? "So, you want me to do all the work, huh?" she asked playfully, grabbing my wrist and pulling my hand away from her.

She put my fingers in her mouth and sucked as she gently grabbed my prick with her free hand. After a few seconds, she pulled my fingers out of her mouth and let go of my wrist. "I love the way my pussy tastes."

She aimed my cock at her pussy and split her lips with the tip. With my cock firmly between her pussy lips, she leaned back, putting her hands on my knees. Her pussy was perfect. It was a sexy, light pink color, and her lips were petite. I looked up at her. Her body was just as impressive. Leep still had her shirt and bra on, but now I could tell just how small and toned she was. We made eye contact, and she smiled a little as she bit her lower lip. "Are you ready, baby?" she asked.

"Yeah."

Leep spread her legs to lower herself down on my throbbing fucker. I ran my hands up along the inside of her silky inner thighs. She started moaning about halfway down my shaft, which is when I started using my thumb to massage her clit. It felt like I was putting my cock in a vise. "Goddamn, you're tight," I said, moving my free hand up her side.

"Oh, fuck," she growled through clenched teeth, closing her eyes and throwing her head back as she reached the base of my cock, "it feels like your gonna rip my cunt open."

We were both still for a moment, each of us trying to adjust to the other. I grabbed one of her breasts over her bra. "Take your shirt off so we can get you outta this bra," I told her.

"hold my back," she replied, lifting her head and looking back at me. I moved my hand around to the small of her back, holding her up when she took her hands off my knees. "The clasp is in the front," she said, unhooking her bra and letting the cups fall.

Leep's tits were on the small side, a B-cup at best, but they were nicer than most. They were nice and round, and they stayed in place when she let her bra fall. Her nipples were clearly hard, like erasers. Her areolas were a dark pink and perfectly round, about the size of nickels. "Are you on birth control?" I asked, looking back up at her face.

"No."

"Well, just so you know, I'm not pulling out," I told her.

"I don't care," she replied, "it's been a long time since I've had unprotected sex and even longer since I've had a guy cum in me. The last time was back in high school, and I miss the way it feels."

"High school?" I asked, "How old are you?"

"Twenty-two."

"Oh, ok," I replied, "When was your last period?"

"A couple of weeks. Honestly, if you cum in me, it's, like, fifty-fifty that you'll knock me up," she replied, putting her hands on my knees as she leaned back again.

"Oh, darlin', I haven't been laid in months, so there's no if," I told her, running my hands up her sides, "I'm going to drop this four-month load deep in your tight, young cunt."

"Ok, if that's what you want," she replied, "at least you warned me. Keener told me you didn't even tell her you came."

I couldn't help but laugh at the memory of creampie surprising Keener. "Yeah, well, she got what she deserved. She's a whore," I replied.

"Yeah, maybe, but she did get pregnant right around that time, and it wasn't her husband's," she said, as she began gyrating her hips a little.

"Didn't she also got walked out of here one night when she was caught with a sergeant balls deep in 'er in a cleaning closet?" I asked.

"She told me she was already pregnant when that happened," Leep replied, "plus, she said he didn't finish."

"I don't really give a fuck," I told her, "why are we talking about Keener anyway? Would you rather I think about her right now? She's hotter anyway."

"Maybe her face is cuter, but my body is far better than hers, and you know it," she replied, gyrating her hips faster and wiggling her shoulders, "so, real quick, why did you warn me?"

"What? About cumming in you?"

"Yeah, after talking to Keener, I already expected you to do it. So, why did you warn me? I mean, it's not like you gave me a choice," she said.

"I don't know. I like you better, I guess, and Keener and I didn't talk much," I replied, "besides, Keener's a fuckin' whore, a cum-bucket. So, I treated her like one."

Leep stopped moving her hips. "Oh," was all she said in reply.

"Am I wrong?"

Leep shrugged her shoulders. I moved my hands down to Leep's hips, and I didn't have to encourage her much to move her hips again. "You've got a sexy, little pussy," I told her.

"Thanks. Your cock is so fuckin' awesome," Leep replied as she looked down between us and pointed at her stomach just above her belly button, "it feels like you're all the way in my stomach."

I had moved one of my hands back to her mons, so I could use my thumb to massage her distended clit again. Leep moved her hips around, but she wasn't moving up and down my cock at all, and I was a long way from cumming. "Do you cum easy?" I asked her.

"Keep playing with my clit," she whispered, between quiet moans.

I did just that. It wasn't long, and I felt Leep's pussy starting to clench around my cock. She wasn't moving her hips as much, and I could tell she was about to cum. I eased my hand from her hip to the small of her back and then up between her shoulder blades. "C' mere," I told her, pulling her to me.

Leep leaned forward and put her forearms on my shoulders, intertwining her fingers behind my head. "Are you cumming?" I asked, whispering in her ear.

I kept circling her clit with my thumb and applied a little more pressure. I rubbed her soft, smooth back at the same time, encouraging her to get closer to me.

"Yeah," she whispered back, now obviously in the throes of an intense orgasm.

Leep was trembling. I pulled her closer and kissed her. She responded instantly, tightening her arms around my neck and pushing her tongue into my mouth. I held her tight as she rode out her orgasm. After a few seconds, her body went limp. "Are you ok?" I asked playfully.

"Oh, god, yes," she replied breathlessly. "your cock is fuckin' amazing. That was the most intense orgasm I've ever had. I can't believe I came that hard from just having you inside me while you played with my clit."

"Really? The most intense, huh?" I asked, trying not to sound too sarcastic as I thought to myself, "Why do all women say that?"

Leep obviously caught my sarcasm, "Yes, really," she replied, sitting back so she could look at me.

She was covered in a layer of sweat and fine hairs that weren't pulled back in her ponytail were stuck to her forehead. I put my thumb back on her clit and she instantly started quivering and her pussy got noticeably tighter around my prick. "You're only the fifth guy I've ever been with."

I grabbed Leep's ass cheeks and lifted her up. "Oh, yeah?" I asked.

My cock was covered with her warm pussy juices and throbbed as the cool air hit it. "Yeah," she replied, giving me a coy smile, "and you're way bigger than my vibrator too."

We looked at each other for a long moment then Leep grabbed my wrists and pulled my hands away from her ass and placed them on her tits firmly. She moaned as she eased herself back down on my throbbing shaft. She was still incredibly tight, and this wasn't going to get me off. I moved my hands around to her back and laid her over on my bunk on her back without my dick coming out of her. I was now on top of her, between her legs, as we laid awkwardly on my narrow bunk. "Aww..." Leep teased, "you want to make love to me missionary, huh?"

I tried pushing my cock deeper into her, but it started to bend in the middle. "Would you like that?" I asked.

Leep bit her lower lip and nodded. "Too bad, slut," I replied, sitting up on my knees.

My dick slipped out of Leep's pussy and I was shocked she wasn't gaping open, even a little. Her fuckhole closed completely and her lips touched. She definitely had a sexy, little, pink pussy. I grabbed both of her legs behind her knees and lifted them up, holding them together. "When was the last time you had your pussy eaten?" I asked her.

"It's been a really long time since I've done anything, like, a year or more," she replied, "and I don't think the last guy ate me out. But I don't know how much time I have left, you don't ha..."

She didn't have a chance to finish before my mouth was on her tight, wet cunt. I pushed my tongue between her pussy lips and licked all the way up to her clit, lightly flicking it with the tip of my tongue before licking back down again. Leep's pussy was saturated with her cum and she tasted kind of sweet, it was no wonder she was anxious to taste herself. I moved my hands down to her ass cheeks and spread them open, using my tongue to rub around her puckered asshole. Leep inhaled sharply. I moved down, quickly giving her little taint a kiss before lightly licking her asshole again. She started to moan quietly as I slid a couple of fingers into her well-lubed twat. She was still tight, and I had to push hard to get my fingers all the way in her, all the while I licked her anal rim. I pushed the tip of my tongue into her ass causing Leep to nearly scream out, "Oh, fuck!"

"Easy, girl," I said, looking around her legs and pully my fingers out of her snatch,

"Sorry," she whispered, "no one's ever licked my ass before."

I didn't respond. Instead, I put my wet fingers at her asshole and kissed her clit. I applied a little pressure on her anal opening and to my surprise she pushed down, easing my finger into her ass to the first knuckle. I began eating her pussy, licking slowly between her pussy lips and sucking on her clit. I kept pushing my finger into her ass, and she kept pushing down. It didn't take long before my entire finger was buried in her tight asshole. Leep was moaning like a whore in heat. I decided to see how she would react to me trying to get another finger in her ass. She didn't resist at all, and it wasn't long before I had two fingers all the way in her ass. "I think I'm going to cum again," she moaned.

"You like having your tight, little asshole fingered, don't you, slut?" I asked her.

Leep didn't answer me, she was lost in another orgasm. Her body quivered again as she moaned. I pulled my fingers out of her ass and sat up on my knees. As much as I enjoyed eating her pussy and fingering her asshole, I was desperate to have my aching cock back inside of her tight cunt. I noticed she still had her panties tangled around her foot and ankle, so I took them off and wiped her dripping pussy with the crotch. "What are you doing?" she asked, trying to catch her breath.

"Wiping your cum on your panties so they smell like you," I replied.

"Why?"

"You didn't think you were getting these back, did you?"

"Well, I, uh..."

"No. I'm keeping them," I told her, "just like I kept Keener's"

"You still have Keener's panties?"

"Yeah. She didn't tell you that?" I asked.

Before she could answer I tossed her skimpy panties onto the desk behind me then grabbed my cock and aimed it at her pussy. "What do you do with them?" she asked.

I parted her pussy lips with the tip of my dick and slid it along her wet sex crack. "I smell them while I beat my dick and think about how good her pussy felt, especially when I came in her by surprise," I told her, moving my cock and sliding the length along her clit, eliciting another gasp as her body trembled.

"Are you gonna sniff mine when you jerk off now? She asked, trying to steady her voice.

"Of course," I replied, still working my shaft over her pussy lips and clit, "so far, you're the better fuck, and your pussy is a lot tighter."

"That's so fuckin' hot," she said.

"What?" I asked, not sure if she was referring to what I said or the feeling of my cock over her clit.

"All of it," she replied, "telling me I'm better than Keener and rubbing my pussy with your big dick while telling me it's tighter than hers."

I didn't respond, it was time to fuck her. I pulled back enough to line my prick up with her fuckhole. "Are you ready to make me cum, slut?" I asked, pushing forward slightly, waiting for her response.

"Oh, god, yes," she replied softly, "fuck me and cum inside me, baby."

Without warning, I slammed my cock in her pussy. "Aww... fuck!" Leep screamed out.

"That's it. Scream, slut," I told her.

I pushed Leep's legs forward, all the way to her chest, putting all my weight on them as I continued to fuck her tight pussy hard and deep. I was taking my time, driving my cock into her at a slow, steady pace. She grunted as she took the full, unforgiving force of me repeatedly slamming my fuck-spike into her. "Oh, god, fuck me, baby," she moaned between grunts.

I sped up, fucking her even harder. The cell was filled with the sounds of Leep's grunts and moans, our pelvises slapping together, and the sloppy sound of her drenched cunt taking my cock as I pounded away at her. Once I was able to get set in a good, steady pace I was surprised, I didn't last much longer. "I'm gonna cum in you," I told her.

"Yes, do it, baby. Cum inside my pussy," she replied in a sexy moan, "I wanna feel you fill me up."

I slammed my throbbing fucker into her one last time and unloaded nearly four months worth of semen deep in her tight cunt. I lost count after the fifth pump, and I wasn't close to finished yet. "Oh, shit! I'm gonna cum too," she moaned.