She’s My Cherry PI
I suppose I could take credit for it but in point of fact, it was just one heck of a lucky break. Well maybe I was lucky or maybe she was just unlucky. Either way, I got lucky in more ways than one.
I’d just entered the building to see my girlfriend. Not an unreasonable thing for a guy to do unless of course you’ve got a wife like I do. Then, you’re not supposed to enter a building to see your girlfriend because quite frankly, you’re not supposed to have a girlfriend. Of course, to be fair, if you knew my wife, maybe it would be obvious just why I had a girlfriend. Meg could be, well let’s just say she could be a bit of a shrew and let’s leave it at that.
Meg wasn’t always the shrew that she’d become. In fact, when we met, she was actually quite demure. She always seemed to want to defer to me which of course, being a guy, I totally liked. Of course, it always sucked when something like her birthday rolled around. “What do you want?” I’d ask.
“Anything,” she’d say.
“Come on, Meg. You know that isn’t going to fly. I got to get you something. What do you want?”
“I’ll like whatever you get me.”
“No come on. What do you want?”
I think you get the picture. Meg expected me to know what she wanted and heaven help me if I wasn’t right because damn it, I was supposed to know what she wanted.
I don’t know what I thought was going to happen when we got married. I suppose I thought everything would just keep going on just the way it had before. Silly me. I should have known better.
When we got married, Meg got totally jealous and by totally jealous, I mean off the deep end kind of jealous. She wanted to know everything about me. She wanted to know where I was. She wanted to know when I left work and if I went out for a drink with the guys, she’d call me up with some dumb ass excuse just so she could make sure I was where she thought I was.
Maybe it was almost inevitable then. As jealous as she was, I suppose maybe I did start to look around and wouldn’t you know it, I found someone I liked better than Meg.
Of course, it wasn’t like I was going to tell Meg that but it was almost fun to try and get around her. I’d take off from work in the middle of the day and I’d go meet Kylee or we’d meet up after work and I’d just happen to “forget” and leave my phone in the car. In a way, it was kind of cool to think that for all her nagging, I was still pulling one over on Meg.
I suppose I should have known I wasn’t as smart as I thought I was.
Like I said, I’d just gone into the lobby of Kylee’s building when I’d realized I’d left the gift I’d bought for her in the car. Dumb really, but no big deal. Just go out and get it, right, except when I went back out of the lobby, there was this jogger. Not a big deal except that the same woman had crossed my path just moments before as I’d gone into the building and that’s when I knew it. I was being followed.
I went out to my car but I never took my eyes off of the jogger. She’d gone to the end of the street and she’d stopped. She was pretending to stretch but she wasn’t fooling me. Not anymore, she wasn’t.
I called up Kylee. “Hey,” I said when she picked up the phone.
“Where are you?”
“I’m downstairs.”
“Well come on up, Silly.”
“I would, but you know what? I think my wife’s hired someone to follow me.”
“You’re kidding.”
“I wish I were,” I said, “but I’m not.”
“Is she pretty?”
“I guess. Why?”
“Where’s she now?”
“At the end of the street. She’s doing some stretching or something.”
“What’s she look like?”
“What?”
“What’s she look like?”
“Brown hair. Purple shorts. Yellow top. Walkman. She’s got big tits.”
“Yeah, you would notice that, wouldn’t you?”
If it had come from anyone else but Kylee, I might have been worried but let’s face it, Kylee’s got a pretty good set of tits herself and she knows what I like and I had a feeling she really wasn’t all that jealous.
“Why don’t you just hang on down there and I’ll see you in a bit.”
“You’re coming down here?”
“Of course.”
“She’s going to see you,” I warned.
“Oh I certainly hope so. In fact, I’m counting on it,” and with that the line went dead.
What the fuck did the girl have in mind, I wondered. I mean sure, I knew Kylee could be a bit impetuous. Heck, she was only 23 but she seemed to think she could get whatever she wanted whenever she wanted and she had this habit of not thinking things all the way through to the end. That was my job but I’ll admit that it did make for a bit of a roller coaster ride from time to time.
I didn’t have long to wait before I saw what Kylee had in mind because I saw her come out of the building and then I saw her start to walk up the street. Okay, just what the heck was the girl up to.
I knew she’d already locked in on the detective. I mean come on, how many women are there wearing purple shorts and yellow tops and it was clear to me that Kylee was heading straight for the woman.
To be honest, I didn’t see exactly what did happen. One moment, Kylee had stopped to say something to the woman and then the two of them were talking and the next moment, the detective had just sort of doubled over and as she slumped down, Kylee was kneeling beside her and then Kylee was helping her to her feet and then even more amazingly, Kylee was helping her back to her apartment.
What the fuck?!
I watched them disappear into Kylee’s building and then they were gone.
It was about fifteen minutes later when I got a call on my cell phone. It was Kylee. “You can come up now,” she said and again the line went dead.
Okay, what the hell was going on, I wondered. Should I go or had Kylee suddenly switched sides and was I going to be in more trouble if I did. Or even more likely, did Kylee think she had things under control when she really didn’t.
The thing was as good as my questions all were, I knew it didn’t matter because I knew I was going to go so I got out of my car and up I went.
Kylee met me at the door. “It’s about time you got here,” she said with a smile.
“I was wondering what was going on up here.”
She smiled. “Actually, you were worried about what was going on here, weren’t you?”
“Well yeah.”
“Come on. You should know me better than that. I always come out fine in the end.”
Well yeah, I told myself, but sometimes only just barely and sometimes, she didn’t get out without a little help from her friends.
“Would you like to meet her?”
“Who?”
“Sheri.”
“Who’s Sheri?”
“She’s the private detective, Silly. I think you should meet her.”
This was dumb, I told myself. If there was anyplace, I shouldn’t be, it was in Kylee’s apartment with a detective that my wife had hired and yet as dumb as I knew that to be, I let myself be drawn into the apartment.
Kylee motioned to the woman sitting on the edge of the couch. “This is Sheri,” she said.
The woman was just sitting there. She didn’t move at all. She was staring straight ahead and if it weren’t for the fact that her eyes would blink from time to time, I might have thought she was a statue.
Kylee giggled. “Sorry, I forgot to release her.”
Release her, I thought. What the heck was Kylee talking about?
“You can talk,” Kylee said.
The detective took a breath of air almost as if she’d been holding it. “Hi,” the woman said.
Nothing I could do about it now, I thought. She was still looking straight ahead but I already knew she’d seen me. There was going to be no way I was going to get out of this easy.
“This is my boyfriend, Doug,” Kylee said and I couldn’t help but groan at that. There was no way we should be giving out free information like that.
“Nice to meet you,” Sheri said in a near monotone.
“Sheri, Doug here would like to see your tits. Would that be okay?”
“Sure,” the woman said and then without any further ado, she took off her top.
“You need to take off your bra, too, Sheri.”
“Oh. Okay.”
She took off her sports bra and suddenly, I could feel my dick getting harder and harder as I just watched her sitting there. I wanted to look at Kylee but I just couldn’t. I had to watch the woman sitting there. “What’s um, what’s going on?” I finally asked.
“I think that’s rather obvious,” Kylee said. “She’s got her top off. Did you know her tits are full of milk?”
It took me a moment before I could answer and still, I couldn’t take my eyes off of Sheri. “What?”
“Her tits. They’re full of milk or maybe they will be. She’s a regular moo cow, aren’t you, dear.”
“Moo,” the woman on the couch said. Not moo like she was just saying it. Not moo like a human would say it, but moo like a cow would say it.
“Oh my,” Kylee said. “I think someone needs to get her tits milked, doesn’t she?”
“Moo,” Sheri moaned again.
“Doug, do you think maybe, you know, we could help her?”
I wanted to ask her just what the heck she thought I should do but before I could open my mouth, I seemed to know exactly what I could do. Heck, she’d already said it herself. She was a moo cow and she totally needed to get her tits milked.
I leaned down and then I was kneeling in front of her. “So someone needs to get her titties milked,” I said.
“Moo!”
“Don’t you worry,” I told her. “I got what you need. I got what you need right here,” and that’s when I started to suck on her tits.
“Moo,” she moaned contentedly.
I know what you’re thinking. How could I know that? How could I know she was moaning contentedly? Well, I don’t know how I knew it, I just knew she loved having me suck on her tits and the more I sucked on her tits, the more I knew she loved it.
“I think she needs something more,” I heard Kylee say.
I might have asked what Kylee meant but I already knew. “Stand up,” I told Sheri.
She stood.
I’d already seen her big, beautiful tits but I’d yet to see her pussy and I knew what I wanted. “Take off your shorts,” I told her.
She took off her shorts and I couldn’t help but notice that she had a nice ass. Not too small mind you but not too big either. It was just a nice ass that just seemed to fill her panties up just right. God, I loved that ass.
All she was wearing now was her panties and I knew what I wanted. “Take off your panties,” I ordered.
Again, she complied and until that moment, I hadn’t realized just how beautiful her pussy was. It was in fact the most beautiful pussy I’d ever laid my eyes on.
“What do you want to do?” I heard Kylee whisper.
“I want to fuck her.”
“Well don’t let me stand in your way.”
I wasn’t. “Sit down,” I told the other woman and again, Sheri did exactly what I told her to do.
“I got something for you,” I said.
“You’ve got something for me?”
I nodded. I couldn’t believe I was doing this but there I was, taking my shirt off and my shoes. I took my jeans off and I could feel my cock straining against my underwear and when I took that off, my cock was suddenly free. To tell the truth, I don’t think I’d ever felt as hard as I’d felt as I was right there.
“Do you like this?” I asked.
She nodded. “I like it.”
“You want to suck it?” I asked.
She hardly sounded all that enthused but when I brought my cock forward and offered it up to her waiting mouth, she showed me just how excited she really was.
As she sucked my cock, one hand slipped behind my leg while the other one reached around me to grab my ass and she wasn’t just grabbing it. She was squeezing it and she was stroking it and if her touches were any indication, I had the feeling that there was no way she wanted to let my cock get away from her mouth.
I could have cum right there and I have little doubt that she would have made me do it if I’d let her but there was so much more that needed to be done. I pulled back and her mouth tried to follow me. “We have to stop,” I said.
“Why?”
Truthfully, it was a hard question to answer. There was a part of me that wanted to just keep on going but I knew I was going to get something even better if I stopped her. “We just have to,” I said.
“Oh. Okay.”
Yeah, that’s right. She accepted it, just like that and I found that rather hot. “I’m going to fuck you,” I said.
“Mmm, I know. I want you to.”
That’s all I had to hear. I tipped my little moo cow back. “Spread those legs,” I told her.
She spread them and moments later, I was there, sliding my cock into her wet and waiting pussy.
“Do you know what she told me?” I thought I heard my girlfriend whisper although honestly, how could I have heard that, and yet I was sure I heard her in my mind.
“She said she’s never been fucked before,” I thought I heard my girlfriend whisper. “She says she’s been looking for just the right man who could fuck her virgin pussy.”
I couldn’t help but groan. It couldn’t possibly be true but what if it was. What if I was getting a pussy in mint condition.
“It’s true,” Sheri moaned.
“What is?”
“I’m a virgin, or at least I was. Oh my God.”
I didn’t care if she was or not. All I knew was I wanted to fuck her. All I knew was I wanted her pussy.
“Oh my God,” she moaned. “Oh my God.”
I was so close to cumming. It wouldn’t take that much more.
“Can you,” she asked and then she stopped and then she started again. “Can you—”
“Can I what?”
“Can you—”
“Can I what?”
“Can you cum in my pussy?”
“You want me to cum in your pussy?”
She nodded.
“Sure, Baby,” I told her. “I can give you whatever you want.”
“Just one thing though.”
“Yeah, Baby. What’s that?”
“I’m not on birth control. If you cum inside me, you’re going to make me pregnant.”
Fuck.
“But I want you to do it. I want you to fill my tits up with milk.”
Fuck. I knew I shouldn’t, but—
“Please, Baby,” she purred. “Please. I want it bad. I want you to fill me up. I want you to fill my tits up with milk. I want you to make me your moo cow.”
Fuck yeah, I couldn’t help but groan to myself. I knew I shouldn’t but I knew I wanted it, too. She wasn’t just Sheri. She was my moo cow. I thought it was a cute nickname and I wanted her tits too always be full of milk.
“Please, Baby, please.”
“You want it?” I asked her.
“Yeah, I want it.”
“Okay. If you want it, then here it comes.”
Okay, maybe it was wrong of me to do but if you’d been there, if you’d heard Sheri moan the way I heard her moan, I think you’d agree with me that making Sheri moan was the only thing I could have done.
“I think I’ll leave you two alone.”
I looked up and I realized that my girlfriend was getting ready to leave. “Where are you going?” I asked.
“You don’t need me,” she said. “You’ve got a new friend.”
“But—”
“You’re a great guy and all that,” Kylee said, “but really, it’s time I was moving on. There are other places to go and other people to see.”
“But—”
“Aw, poor Doug. Still worried about what your wife might think.”
I wasn’t worried about that at all. In fact, up to that very moment, I hadn’t given Meg a second thought.
“Just so you know. You shouldn’t worry abut that. I’ve already taken care of that.”
“You’ve already taken care of what?”
“Your ex-wife, Silly.”
“My what?”
“Your ex-wife. She was holding you back and she was bringing you down so I took care of her.”
“What’d you do?”
“Let’s just say she’s got someone else to focus her fixations on.”
“Who?”
Kylee just smiled at me. “You have to realize it doesn’t work that way. Let’s just say that she’s not thinking about you anymore so you shouldn’t be thinking about her. Besides, you’ve got your little moo cow to take care of.”
I looked back at Sheri with her fucking big tits and I realized that Kylee was right.
“Doug,” Sheri whined. “Can you fuck me again?”
“I think someone wants your attention.”
I’ll admit it. For just a moment longer, Kylee had my attention. I wasn’t sure just what the heck it was that she’d done but whatever it was, I knew I liked it and I knew I couldn’t wait to get back to fucking Sheri’s ever loving pussy.
“Coming,” I said.
“Have fun with your new life,” Kylee said and I knew she was already heading for the door but I just didn’t care.
I looked at Sheri. “How about we stick my cock in your little cherry pie,” I told her.
“Mmm yeah. You know exactly what I want,” she purred.