Chapter 40: Firsts, Part I

January 1981, Milford, Ohio

On Monday morning at school, Tracey Jones pulled me aside and told me she had a question she needed to ask me. She and I were on different lunches, so I asked if I could call her, but she wanted to talk face-to-face. I suggested that I’d drop by her house after I saw Doctor Mercer that evening if she wanted, and she was fine with that.

When I walked into Miss Barkhurst’s class, where I was the teaching assistant, I sighed. Dona Bingham was in this class. She looked daggers at me when I took my seat by the lab table at the front of the class next to Miss Barkhurst’s desk. There wasn’t much I could do about it.

Bethany was still on the same lunch as I was, along with Kathy, Larry, and Brent. This was the smallest group that we’d had in quite some time. I noticed also that the ‘Holy Rollers’ table had only four or five people, including Kara, where they’d had twelve last quarter. It was almost as if whoever made the schedules was working against all of us.

After school, I dropped the girls at home and went to my appointment with Doctor Mercer. She was, once again, happy with my progress, but given the way things had gone before, she wanted to keep seeing me for several more weeks. I laughed at her comment and readily agreed because she was absolutely correct.

When I left her office, I headed over to Tracey’s house. Tracey’s mom let me in, telling me how glad she was to see me, offered me a Coke, which I accepted, and then Tracey led me to their finished basement. We sat on the couch to talk.

“Steve, uhm, I have some questions,” she said, turning a bit red.

“You can ask me anything!”

“Well, I’ve been going out with Marty Heller and, well, we kind of fooled around.”

I chuckle, “Kind of? You can just tell me. I’m not going to get upset. I can only answer questions if you ask them, not if you beat around the bush.”

“Sorry. I should know better with you,” she smiled. “We went on a few dates and then, during Christmas break, we had sex. It was OK. I liked it and all, but he’s not as experienced as you are.”

“Tracey, from what I’m told, and not to brag, nobody in the school is as experienced as I am!”

“True,” she giggled. “Sorry. So far he’s licked me, I’ve given him a blowjob and we’ve had regular sex. Then, on New Year’s, we were at a party and had a bit to drink. We were fooling around in a bedroom at the house we were at. We wanted to try it doggie-style, and at one point he slipped out and bumped into my butt. I giggled and then he asked if we could try, you know, doing it there. We’ve heard people can do it that way. Well, it hurt like hell, so we stopped. Do people really do that or is it just a rumor?”

“He just tried to put it in without doing anything else?”

“Yeah.”

Good god, it was a wonder she could walk! That must have hurt like hell. It was bad enough when Jennifer had stuck her vibrator in my butt after putting baby oil on it.

“No wonder it hurt! First of all, you really need to use lubrication, like baby oil or Vaseline. Second, if you’ve never done it before, he should use his little finger first, then a larger finger, before he even tried to do it. I’m not surprised that it hurt like hell!”

“I guess we had no idea how it was supposed to work. So people really do that? And they like it?”

“Yes, they do it. Some people really like it, others don’t.”

“And you? Have you done it or do you just like know about it from a book or something?”

“I’ve done it,” I said.

I saw from Tracey’s look exactly what she was going to ask next. She was silent for a moment, though.

“Could you, uh, show me how to do it? I know I’m not supposed to ask you for sex, but this is like a teaching thing, you know, like being the lab assistant,” she said, turning bright red.

I didn’t really see any harm in it, so long as she wasn’t going steady with Marty.

“Are you and Marty going steady?”

“No, we aren’t. He knows I was going to ask you about it. We both want to try it, but he had no clue who he could ask.”

“Did you tell him you were going to ask for a lesson?”

“No. But he’ll be OK with it. He knows you took my virginity.”

“And how does he know that?” I asked with a wan smile.

“I told him, silly. He and I both told each other who our firsts were. His was...”

“STOP!” I commanded. “I do not want to know and I don’t need to know.”

“Wow, Steve, what’s the big deal?”

“I do not talk about stuff like that. Guys should not talk about who they’ve had sex with. It’s a rule I follow. In fact, if you talk to any of my male friends, they might guess that I’ve had sex with certain girls, but I never talk about it with them. Ever. If I did, it would eventually get back to girls who then would never want to do it with me because everyone would know. Anything you’ve heard has come from the girls, not from me!”

“I guess I see your point. Sorry. So, will you show me how to do it?”

“Yes, I will. When?”

“Tomorrow, if you’re free.”

“You don’t want to waste any time, do you?” I chuckled. “I’m TA at the computer lab at the Junior High after school. How about I pick you up around 7:00pm?”

“Cool! Thanks!” she gushed, then moved closer to me and gave me a deep kiss. “I’m looking forward to it!”

I headed home for dinner and started reading All the King’s Men by Robert Penn Warren, on which I was planning to write my Senior thesis paper. It was a fictional story, but it was based on Huey Long, a Southern political boss. I didn’t have any other homework, so I managed to read about forty pages.

On Tuesday, after a normal day at school, and the usual flirting from Krista King in the computer lab at the Junior High, I headed home for dinner. I ate, did part of my physics homework, then went to get Tracey. She bounced out of the house as soon as I pulled into the driveway and hopped into the car as soon as I had stopped.

“You seem a little excited, Tracey!”

“I am! I really want to learn how to do this. I told Marty I’d know how to do it this weekend!”

She was the most enthusiastic girl I’d ever seen with regard to anal sex before even having done it. With the exception of Katt and Jennifer, it was mostly experimental or a one-time thing. With Jennifer, it had been experimental and in her wild moments, she wanted it. Katt liked it and wanted it all the time. That made me wonder what Mikael would think. But with that firm butt and fantastic muscle tone and control, what was not to like?

When we got to the building, Tracey practically dragged me upstairs and into the apartment.

“So, what do we do?” she asked, grinning.

“That depends on you.”

“Could I talk you into licking me and fucking me the regular way first?” she said, cocking her head slightly.

“Sure,” I chuckled. “What about protection?”

“I put my diaphragm in before I left home!” she said with an impish smile as she unbuttoned her blouse and shrugged it off.

“Why do I have this wild thought that you’ve planned this all along?” I said with a smile.

“Well, no harm done if you didn’t give me a regular fuck first, but why not take a chance and ask?” she said and removed her jeans.

“One good tongue lashing and one good fucking, coming right up!” I said, removing my shirt and jeans.

Tracey removed her bra and panties, turned down the bed, and got in.

I removed my underwear and got between her legs and, without warning, shoved my tongue as deeply into her pussy as I could. Tracey groaned and lifted her hips to push her pussy hard into my face. I licked and sucked and kissed her to orgasm, then moved up, positioned my dick and pushed it all the way in with a single hard stroke.

“Ungh!” she groaned. “Fuck me, Steve!”

I fucked her hard and fast. We screwed furiously for a few minutes before she arched her back and came hard. I was right behind her, firing jets of cum deep into her pussy.

Tracey sighed, “Damn, that was good! Now, cuddle me until you can do it again!”

“You’ve become quite confident!”

“Well, you taught me. You were right, by the way. Marty thinks I’m fantastic in bed and he likes having sex with me. He just needs practice. And I’m going to give him lots of chances to practice!”

“It’s ALIVE! I’ve created a monster!” I said in a theatrical voice.

“No, you didn’t create me,” she laughed, smacking my chest. “You just let me see myself as someone who was desirable. Marty likes my body!”

“So do I! And having an enthusiastic partner really helps.”

“I’ll show you enthusiasm, Steve Adams!” she said, pushing me over onto my back.

She moved down and licked my dick clean, then sucked me to an erection very quickly.

“I’d let you cum in my mouth, but I know we have limited time! So, teach me!” she demanded.

“Turn on your stomach, please,” I said, slipping a pillow under her to provide a better angle.

“The pillow helps, because it makes your butt stick up in the air a bit,” I said.

I opened the drawer next to the bed and pulled out the jar of Vaseline.

“First, I’m going to rub some Vaseline on you, then on my pinky. I’ll gently push that in, and then when you’re OK, I’ll do the same with my index finger.”

“OK, Steve. Go ahead!”

I got a big blob of Vaseline on my finger and rubbed it up and down between her cheeks, making sure I got plenty on her hole.

“Oooh, that feels different.”

“I’m going to push my little finger in now. Just relax, please.”

She let out a deep breath and visibly relaxed her muscles. I put some Vaseline on my pinky and placed it against her hole, and gently pushed. It popped in quickly.

“Oomph!” Tracey groaned.

“Everything OK?”

“It just feels strange. Go ahead. Just do it all and don’t worry about asking!”

I slowly pushed my pinky in as far as I could, wiggling it around a bit, causing Tracey to moan softly. After a few minutes, I pulled my little finger out, then put some Vaseline on my index finger. I pressed it into Tracey with one smooth motion.

“Ungh!” she grunted.

I moved my finger around a bit, then slid it most of the way out and pushed it all the way back in.

“Ungh!” she grunted again.

I repeated the motion a couple of times and decided that she was clearly ready. I slowly withdrew my finger and wiped it with a tissue.

“Push your hand between your legs and rub your clit or finger yourself. It’ll help you cum,” I said.

She quickly did so, pushing the tips of two fingers into her pussy. I put quite a bit of Vaseline on my dick, positioned it against her rear entrance and pushed forward, causing my glans to enter her, feeling the extreme heat surrounding me.

“Unnngggghhhh!” she groaned loudly.

I pushed forward and slowly entered her. When my pubic hair touched her butt, I stopped and waited, enjoying the tight sensation of her butt around my dick.

“It feels so full!” she gasped. “Do it, Steve. Fuck me in the butt!”

I saw her begin to furiously finger herself as I pulled back and pushed forward. Each time I pushed all the way in, Tracey grunted. I made several slow in and out strokes and then increased my speed. Tracey was gasping for breath and actually pushing her butt up to meet my strokes as she worked her fingers into her pussy.

“I’m going to cum!” she gasped, then a few seconds later screamed into the pillow as a massive orgasm overtook her.

A few more strokes and I pushed as deeply as possible and fired jet after jet of hot cum into her butt. I lowered myself onto her and we lay there for a few minutes, trying to catch our breath. When my dick started to soften, I pulled out of Tracey and she whimpered.

“I loved that! I never came so hard, even from your expert fucking!”

I chuckled, “Glad I could be of assistance!”

I got up from the bed and took her hand to help her up.

“Let’s take a shower. I need to clean up. I have to warn you that you’ll leak for a bit.”

“From front AND back!” she giggled.

We showered together, making sure we were both completely clean.

“You know, I might not have gotten that lesson completely right. Perhaps you can repeat it now, so I’m sure!” she said with her impish grin.

“That’s up to Marty from now on. Just make sure you get yourself some Vaseline and take your time. Also, he’s likely to cum right away if you don’t either screw or give him a blowjob first. He’ll be super excited. Don’t criticize him, just keep trying until you get it right!”

She hugged me tight as I turned off the shower and grabbed two towels. We dried off, then got dressed. She helped me change the sheets on the bed, and I realized I’d need to do laundry. I grabbed everything and put it in the washing machine and went back to sit with Tracey until it was done. We chatted and about forty minutes later, I switched the load to the dryer, then drove her home.