Her First Times
I ran through several others that year. There was Kim and Pam and Karen just to name a few. Finally I ran across Teresa.
Teresa was short with long dark hair, and she was the bustiest of all of the girls I'd gotten together with. I actually stopped by Teresa's house one day by accident, and caught her outside playing with her sisters.
She had on some tight shorts that day, and the t-shirt she was wearing made it obvious she was braless. That surprised me a bit. I figured someone with a 38DD chest would have that strapped down no matter what. She didn't though, and as we talked I could see hard nipples saying hello to me. She tolerated my staring with a small smile. Finally after chatting for a while, I asked her out.
She accepted, and we took off into town for dinner and a movie at the local theatre. I even talked her into not changing. After all, I was wearing roughly the same thing. So I had eye candy the entire time we ate.
In the theatre, things got interesting. I put an arm around her, and my fingers were almost brushing the top of her breast. I moved slowly of course, simply because this was our first date. I started off gently running my fingers across the top of that incredible mound, and when she didn't complain or stop me, my hand moved lower.
By a quarter of the way through that movie, my hand was filled with one of those huge tits. She turned her head toward me, smiling in the darkness. I leaned over and kissed her then, moving my hand so it slipped down her shirt.
We played like that all through the very forgettable movie that evening. Her hand even ventured to my thigh, stroking it and moving higher until she found my hard shaft stretched across the front of my shorts. The movie was coming to an end, and so we straightened up and got ready for the lights to come on. When they did, we walked out to my car parked nearby.
I fired the engine up and looked over at her. "Home?"
She smiled at me. "I've got some time yet. So let's not go straight home."
I nodded and smiled myself. I knew what that meant. At least I thought I did at that point. So I drove out to my favorite parking place, all the while imagining her naked under me as my cock filled her up.
We got there and I parked. Turning to her in the dim light, we went right back to where we were in the theatre. This time though, we were alone. We were kissing again when my hand slid up to those massive mounds, and got acquainted with them through her thin shirt. After a few minutes she stopped me, and smiled at my confusion. She reached down then and peeled her shirt off, giving me my first view of those amazing tits.
I'd never seen anything like that in my life, and as she sat there smiling in front of me, my hands went to work. When I got to those incredible hard pale nipples, she moaned. I couldn't resist bending over and sucking those nipples into my mouth one by one. She moaned again, holding my head in place as my tongue lashed those hard nipples. When I nipped them gently, she actually gasped.
"Oh yeah. Just like that."
Eventually I kissed my way back up to her lips, and we continued on. Her hand was stroking me as I played with her tits. Then I escalated things a bit.
My trusty hand slipped to her knee, sliding slowly upward. It came to rest right on her covered pussy. I could feel how hot she was through her shorts, but as I started gently rubbing that hot pussy, she stopped me.
"That's not going to happen Chris. At least not tonight."
I must have looked confused because she explained.
"Chris, I'm an oddity in this small town. I'm still a virgin, and I've got no plans to remedy that situation tonight." She smiled gently at me then. "I really like you Chris. You're the first guy ever to see me topless. But I'm not climbing out of the rest of my clothes tonight. To put it bluntly, we're not going to fuck."
That completely derailed my plans for the evening, and I was actually at a loss for words. Finally I managed a few though.
"Ok, that's fine. I'm surprised, but I get it. So we wait then."
By the look on her face, it was her turn to be surprised. I could hear it in her voice to add she said, "Thank you. You're the first guy who hasn't tried to pressure me into something."
"Believe me, I thought about it. But talking you into something you're not ready for isn't my style. I want you to want to have fun. I'm not going to push you to do it."
Teresa looked into my eyes, and saw I meant what I said. She really did appreciate it; I could see that on her face. She leaned in then and kissed me again, her hand going back to my lap. I was getting hooked on her soft hand stroking me when she sat back and shocked me.
"You know there's lots of other stuff we can do. If you still want to."
"In the mood I'm in now? I'd love to. What do you have in mind?"
"I borrowed one of my Dad's porn videos one day. Boy was that educational!"
We both laughed at that, and my hopes and my cock were both high. "So what did you see on there that interests you?"
"Everything honestly. It got me so turned on, I started flashing my dates from my bedroom window." She smiled sadly. "Not one of them looked back. They would have gotten an eyeful."
I filed that tidbit away for further use, coming back to the present. "So what caught your eye?"
"The girl on it had huge tits, and she took the guy and did something I'd never heard of." Teresa had me move aside, then she laid down on my front seat. That was exactly what I wanted, other than her damn shorts still being on.
She reached into her purse, and pulled out a small jar that I recognized. It was petroleum jelly, and I couldn't wait to see what she did with that.
She scooped some up, and applied it to her chest and the inside of her tits. I had a good idea what was going to happen then, and I had a surprise for her too.
"Now, get rid of those shorts and kneel right over me with your dick right here." She tapped her cleavage, which was now nice and slick. I followed her instructions to the letter, kneeling over her with one leg on the floor and the other on the seat behind her. I laid my hard cock right in that amazing canyon, and she smiled up at me. Then she pressed her tits together.
That felt fucking amazing. As my hips started moving slowly, I told her, "This is a first for me too."
"Oh nice!" My length was slipping and sliding through that deep canyon then. I noticed her head tilted up, and she explained with a smile.
"You keep poking me in the throat."
"Sorry." It was my first time at that too, and quite frankly, I had no idea what to do. Other than what I was doing of course. The sight and the feel of it were fantastic. I could barely see my shaft sliding between those immense tits, and the lube was perfect. I held out for as long as I could, but when her fingers started tweaking her nipples, I was done for.
The first huge splash of cum blasted her chin, surprising her a bit. The rest I shot between those heavenly tits, making her cleavage even slicker that it had been. I finally pulled out, and those tits dropped, revealing the hot sticky mess I'd left on her chest.
She was smiling though. "So what did you think of that?"
"Teresa, it was amazing. That's the only word I've got for it."
The cum from my first shot was running down her throat then. I smiled at the sight, and an idea hit me.
"Are you ready for another first tonight?"
She looked entertained. "What have you got in mind?"
I ran my finger through the cum painting her throat. I scooped up quite a bit, and held it up. With an evil smile I said, "Stick out your tongue."
That raised her eyebrows, but after a few moments she did. She knew what was coming.
I ran my finger over her tongue, leaving my cum there for her to taste. She was watching me as the taste spread into her mouth, and finally to my surprise, she slid her tongue back in and swallowed.
I couldn't read the look on her face so I asked her straight out. "How was that?"
"Better than I thought it would be. It's an acquired taste isn't it?"
"I'd say probably so." I reached back then and grabbed an old shirt of my own out of the back to clean her up with. I wasn't going to press my luck that night. Although it wasn't what I'd been expecting, it was fun and I realized something.
I really wanted to see her again.
Usually by that point of the evening I'd be thinking about my next conquest. But I wanted to travel down this road with her for a while, just to find out where it would end.
After the customary making out in her driveway, I looked at her before she went in and said, "I'd really like to see more of you."
That wasn't the right thing to say. She laughed and said, "Gee, no kidding?"
"That's not what I meant. I'd like to see you again if you don't mind."
"I'd really like that Chris. I want to see you again too."
"How about tomorrow?"
She agreed to that right away. So I made plans to come out and spend the day with her. As I watched her walk in, I remembered what she said about flashing her other boyfriends.
I pulled out of the drive, and around the corner. From there I wasn't far from her bedroom window. I got out, and stood leaning on my car and smiling.
She came in and walked over to the window, obviously looking out to see where I was. She looked a bit shocked to see me standing there, Her eyebrows raised, and then she smiled. She reached down and stripped off that shirt again, giving me a really good look at those tits. She even shimmied, making them swing. She reached down then, doing something below the window sill. I couldn't see what it was until she came up with her shorts in her hand. I applauded silently, standing up straight to get a better view. She turned around then and walked over to shut off the light. I got a good look at her tight little ass walking away from me, then the fun was over.
When I showed up the next day, all the cars were gone. When she answered the door, she was in my arms and I was kissing her right away. My hands were on that tight ass, groping it as we made out at the door.
When we broke off that kiss she laughed and said, "Come on in."
I apologized for mauling her at the door like that, telling her, "Seeing you like that last night just made me nuts."
She smiled. "It was on my mind too last night."
"I'm betting you slept better than I did though."
Teresa looked at me and cocked her head. "After a little relief, I just might have."
I arched my eyebrows. "Relief? You mean you..."
"I was hot and bothered, so I let my fingers do the walking. Do I need to be more specific?"
I shook my head and grinned. "No, but now I really want to see that."
"I bet you would."
We went into the living room and sat down. As we talked, all I could think about were those delicate fingers playing with her pussy. I lost track of the conversation so many times I lost count. Finally she stopped, shaking her head.
"I've got an idea. Since your mind is in the gutter, let's take advantage of it."
"What have you got in mind kiddo?"
"Let's check out Dad's instructional video. How's that sound?"
It sounded like I might get laid, so I was all for it. She went in a bedroom, and came out with an unmarked video.
"Here it is. It's one of those amateur ones though."
That was fine with me. She put it in the player, and we were off and running. I liked the look of the girl on it. She looked a lot like Teresa physically. The only difference I could see was her hair and face. And she shaved her pussy. I had to ask, being the soul of discretion.
"So tell me. Do you shave too?"
She smiled and nodded. There was another other added to my current fantasy list. Then she said, "Here's what we did last night."
Sure enough, the girl on the screen was getting her tits fucked. That brought back some memories. We kept watching as the girl on the screen did anything and everything. The video ended, and Teresa turned to me to say something, then started giggling.
"What's so funny?"
"I was going to ask you how you liked it, but then I looked." She gestured at my lap, and I knew what she was talking about. The entire time I'd been imagining her doing every one of those things with me.
I told her that too. "I could just imagine you in every one of those positions."
"I don't know." She looked pensive as she said, "Most of them, yes. But I'm having a little trouble imagining you fucking my ass. You're a little big for that don't you think?"
"Oh hell no. Lots of lube and taking it slowly works every time."
"Are you telling me that because you've done it, or because you want to fuck my ass?"
"Both actually."
"Who was it?"
"You remember Karen don't you?"
Teresa looked amazed. "Oh my God! She's tiny! She let you fuck her ass?"
"Among other things, yes. Like I said, lots of lube and patience saved the day."
Teresa leaned over my lap, and I felt that soft hand wrap around my shaft again. She quizzed me as she stroked me gently.
"So what else did she do?"
"Everything. You name it and she was up for it that night."
"Did she let you fuck her? Not her ass I mean.*
"Oh yeah " I got lost in the memory of that evening then, and missed what she asked next.
"I'm sorry. What did you say?"
"I asked if she gave you head. You know, sucked your dick?"
"Of course she did."
All the information seemed to bother Teresa. I saw the frown on her face and asked, "What's the matter?"
"I'm kind of behind here aren't I?"
I thought for a moment before answering. "Let's put it this way. You're not out fucking everything that moves, so you're behind there. But you're going as fast as you want to. That's the important thing I guess."
I smiled and told her, "Would I enjoy you being a complete and total slut? Of course. But I can see your side of it too. You need to do what works for you."
"Thank you for that." She appreciated my honesty. "Maybe I should speed things up a bit."
"Keep stroking me like that, and I'm sure we can arrange that."
She laughed, and I knew we were away from dangerous grounds. I really would have loved for her to be a complete slut, but there was something else. I actually liked being with her.
She was still stroking me, and obviously thinking about what we'd talked about. An idea popped into mind then, and I reached down and stopped her hand.
That shocked her a bit, but I had a reason. *Let's go for a ride."
We got in the car, and headed out. I was getting these looks the entire way. Obviously she thought I was crazy, but I actually had a plan.
20 minutes or so later, we pulled into a small cement block building. She was really confused now, but I held out my hand and she took it, following me inside.
When we got in she gasped. I'd brought her to what was obviously an adult bookstore.
"What in the hell are we doing here?"
I turned to face her, taking her other hand in mine. "Teresa, there's a whole world of fun out there. It's not just your Dad's video. Although it's a good one, I thought you might like to see what else is out there."
To my surprise, she actually agreed. "You're right. Since you're so far ahead of me, maybe I should see what I'm missing."
I knew the guy behind the counter. His name was Bob, and he was checking Teresa out from top to bottom.
"Damn Chris, where'd you get this one?"
"It's a long story buddy. I need some singles please."
He gave me some change, and we headed back to the booths in the back. My favorite was open that day, clear down on the end. I took Teresa to it and shut the door, locking it behind us.
I gave her instructions on how to work the machine, and put in a few bills. She touched the button, and a movie came on the screen. It was a gangbang, and I saw her eyes go wide.
"Damn!*
*There's a lot more in there. Keep flipping through them until you find something you want to see."
She saw it all that afternoon, and I mean everything. Lesbians, guys on guys. You name it, it appeared before her curious eyes. They even had a few classics on there. She checked out I've of the Taboo movies, popping into it right during the orgy scene. Then she found Linda Lovelace in her classic.
That fascinated her, and when the girl on the screen swallowed a huge cock, she was impressed.
"How the hell does she manage that?"
*Lots and lots of practice is my guess." Theresa nodded, transfixed by the sight of that huge shaft sliding right down the stars throat. I took the proteinous opportunity then to slide my hands up from her waist to those amazing tits, playing with them as she watched. She absently reached back and started stroking me through the front of my jeans then. I stopped playing with her for a moment and reached down and unzipped me jeans to give her easy access. As her hand slid into my jeans, she turned and smiled at me.
"Is that a hint?"
"Only if you want to try. Just remember if you do, watch your teeth. That kind of detracts from the fun."
It didn't take too much longer before she told me, "I've got to try that." She reached up and undid my jeans, letting them slip to the floor. She was getting ready to sit down on the bench there when I pulled her shirt up and off.
She sat down, stroking my shaft right in front of her face. Something caught her eye then, and she looked over and then up at me.
"What's that hola in the wall?"
"It's called a gloryhole. There's probably a guy on the other side of it, looking at every inch of those amazing tits of yours and thinking how lucky I am."
She kept stroking me, glancing over at the hole. Finally I told her, "Try it out. Stick one of those hard nipples of yours through it and see what happens."
She cupped one breast and brought her hard nipple to the hole. I watched it go through as far as it could, then I heard her gasp again.
*Someone's licking my nipple!"
I smiled. "I figured as much. The fun part is it may be a guy, and it may be a girl. You never know."
She finally turned away, her curiosity satisfied for the moment. She concentrated on my cock then. She'd stroke me, move forward and then stop.
After doing that several times, she said, "I'm sorry. I'm a little nervous."
"Take your time. You can do this. There's an easy way you know."
"What's the easy way."
"Open your mouth and stick out your tongue." When she did, I laid the head of my shaft on her tongue. We sat there like that for a moment, then she moved forward capturing the head of my cock in what turned out to be an amazing hot little mouth.
She got it down fairly quickly, and was soon bobbing up and down my length. She couldn't take me all the way down, and that frustrated her, but I reminded her that this was her first time, and she was doing wonderfully.
As she sucked away, naturally I got closer to filling that hot mouth. A warning to a first timer is always appropriate, so I told her I was about to cum. She nodded; she was ready for it. So I didn't hold back. I let my load fly, coating her mouth and tongue.
She did what comes naturally, swallowing as my cum flooded her mouth. To her credit, she didn't even gag. I slid out of her mouth finally, and she looked up with a question.r"
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