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Losing My Virginity to My Mother's Best Friend - Part 4

"A high school teen just lost his virginity meets a senior who wants to lose hers."

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Author's Notes

"This is a Part 4 in this series reflecting on how a teen loses his virginity to his mother's best friend, meets a senior who wants to lose her virginity, and who is about to be taken to bed by his own mother. <p> [ADVERT] </p> If you haven't read Parts 1-3, you may want to so that you can be caught up to were we are in Part 4. Oh, and yes, there will be a Part 5."

I walked into the pancake house and looked to see if there was anyone I knew before asking for a table. I didn’t see anyone right off, so I motioned to the hostess indicating an open table by the front windows. This particular hostess just happened to be a senior at the high school I attended and one whom I only spoke to briefly between classes. She worked at the pancake house part-time to put away spending money for college.

She was very cute, even in the hostess attire. She wore light makeup, her luscious full lips with lip gloss made her lips sparkle, beautiful blue eyes, shoulder length blonde hair pinned up atop her head and she smelled so fresh, a vanilla scent. I thought about making a comment like, “Wow, I get to see you out of your street clothes.” Glad I thought about it and didn’t say anything stupid like that.

Her name was Lynnette Bradley and she liked to be called Lynn. She was a member of the high school marching band as one of the flag girls. She was also in the drama club, having been in the high school play each year since she was a freshman.

I took my seat as she placed the flatware and napkin on the table and handed me the menu. “Hi there Tony. Good to see you. What can I get you to drink this afternoon?”

“How about an ice water and a large orange juice, please. Thank you.” I smiled at her as I watched her jot my drink order on her pad. She smiled at me and spun around quickly to head back to the counter. I watched her strut her way across the dining room, amazed at how lovely her ass looked in the tight skirt, her beautiful legs, white ankle socks and white tennis shoes. What a beautiful tan.

Here I was, having just lost my virginity to my mother’s best friend and the first real sex I had ever had other than masturbation. I was euphoric; on top of the world at the moment. I was gazing out the window toward the street watching the cars go by and thinking of Abby’s wonderful sex lessons and what more I was going to learn, let along of the possibilities of having sex with my own mother. What a wonderful dilemma to be in.

I was lost deep in thought and unaware when Lynn came back to the table. She leaned over with my orange juice and ice water and set them down in front of me. “I see you’re a little preoccupied. Waiting for someone else Tony?”

I was brought back to the moment, “I think I missed everyone earlier. I kind of got tied up and didn’t get to the pick-up game this morning. Did any of the group drop in?”

Lynn stood there with her hip cocked to the right and her head tilted slightly. “I just came on shift. I don’t know who was here earlier. On another note, I heard that a group was going to the drive-in this evening. Are you going?”

“I’m not sure. There was talk of going to a movie as a group. Not sure if it was at the drive-in or not though. It might be. If I had made the pick-up game I would know for sure. Now, I have to wait and see.”

Lynn shifted her head and put her pen to her cheek tapping it for a moment. I don’t know what hit me but it sure was suggestive, or at least I thought so at the moment. Wait, was Lynne flirting with me?

“Well, I know you’ve been kind of seeing Becky Harrison.” She quipped. “If it’s not serious or if she doesn’t show up, look for us. Who knows? Now, do you know what you’d like?”

It hit me again. Holly crap Batman! Was Lynn really flirting with me? That never happened before. We only chatted casually in the hall in passing, at parties, and at the pizzeria after football games and other sporting events. Nothing to think that she even had any interest. There was always just casual conversation between us. Or, maybe, my oversexed brain was in overload right now.

“Like?” I asked a little quizzically.

“Yes, what would you like to order?” Lynn smiled at me.

“Oh.” I responded. “Sorry. Easily distracted. How about eggs over easy, bacon, and three pancakes.”

Lynn wrote down my order as she kept looking down at me. “And, who knows about tonight. That’s up to you.” She gave me the most adorable smile and raised her eyebrows. Her blue eyes sparkled and it appeared she batted her eyelashes. She spun around and left me to place my order with the kitchen.

I had to clear my head. I gazed back out the window to the street and the parking lot when I noticed a couple of the guy’s cars pulling in. In all, there were three cars. In a matter of a few minutes, twelve of the guys I played basketball with were standing at the reception podium at the front of the restaurant waiting for Lynn to seat them. Rick, one of the high school team’s captains, junior center and friend, saw me sitting at the table by the window. He waved and put his hands in the air as if to say “Where have you been?”

Lynn grabbed a handful of menus and motioned the guys over to a group of booths near me when Rick slid into the seat across from me and two others, Mark Martin and Tom Reynolds, stood up with their arms resting on the tops of the seats.

Rick asked, “What happened to you Tony? You never miss a pick up game. We played three sets today.”

I leaned back and sipped my orange juice before responding. “I had a few errands to run for my mom and time just got away from me. So, I headed here. Thought I might catch you all here. When I got here, I asked Lynn if you all had been in and she didn’t know. So, I ordered. I thought you all might have already been here and left.”

Shift change in the diner was now complete and there were three more waitresses to help Lynne so that she could focus on the front end of the restaurant although she still had myself and three other tables of customers to handle.

I slid over and let Mark sit down while Tom slid in next to Rick. The others were at booths a few feet away and now handled by the other waitresses. Lynn came over and looked at the new additions to my booth. “I see you didn’t make it here earlier. Tony had asked if you all had been here. Do you three want to order as well?”

All three nodded yes and placed their regular orders, knowing the menu by heart and asking for separate checks for each. Lynn wrote down the orders and gave me a quick grin and a wink as she moved back to place their orders.

I saw the wink. I wasn’t dreaming. She was flirting with me.

We chatted about the pick-up games and Rick brought up going to the drive-in that evening as a group. He brought up finding a place to park near the back and bringing some “beverages”.

Lynn returned with the drink orders for Rick, Mark and Tom. She looked at me and smiled, “And Tony, your order is just about ready. I’ll be right back.” Another wonderful smile and she again moved about to check on the other tables as she made her way back to the counter.

Rick noticed it right off the bat. “Hey, is she flirting with you man?”

The guys chuckled and I just looked at them. “Hey, Lynn and I are not an item. You know that. Besides, she’s a senior and I’m just a sophomore who is looking forward to his junior year. Although, I had kind of had my eye on Becky Harrison.”

“Yeah. Well I say she’s flirting with you. Whatever you are doing, she is sending you a signal.” Rick said with a grin. “Lynn is one of those who’s always been an enigma. She goes to private dance classes, in the drama club, a flag girl. But, I really don’t recall her dating someone steady, at least from our school since I’ve known her. As a matter of fact, there isn’t even any gossip about her.”

Mark chimed in. “Us neither.” He pointed to both himself and Tom. “We always see her at the parties and dances, even the pizzeria, but she’s always with the groups from the band or the drama club. She does go to all of the games for most of the sports though,  football, basketball, wrestling, track and baseball.”

Just as Tom was about to add something, Lynn appeared with my plate of food. She leaned over Mark to sit my plates down in front of me. Her blouse was now snug against her breasts. They were right in front of Mark, whose eyes grew big as Lynn set down the plates. Before she pulled back, she looked me straight in the eyes and said, “Enjoy. I hope you like.”

I responded, “I’m sure I would, or, will.” I know my cheeks were now turning a bit red realizing how my response may have sounded. Although, I absentmindedly think I did it on purpose.

Her quick retort sealed the deal. “I know you will, can, and well, you get the drift.” Another smile and she left.

Rick was the first to respond as I just sat there watching her make her way to check on the other customers. She would casually look over her shoulder at me and smile as she moved about the room. “Yep! That seals it. She’s definitely coming on to you letting you know she’s interested. You catch that?”

Both Mark and Tom nodded and responded in unison, “Yep!”

I smiled and thought to myself, “She may really be interested. Those were suggestive double entendre comments. Glad I paid attention in English class.”

I finally responded to the guys’ jabs, “Oh my. Well, I guess I just might have to make sure I make it to the drive-in this evening to see if you guys are right.”

I began eating as our casual conversations around the booth continued, from cars, to the drive-in tonight, to who was bringing what, who was driving, and what time we would meet up to head over to find a parking place. I was halfway through my meal, often glancing up to see if I could get a glimpse of Lynn making eye contacts several times, each added with a very inviting smile and a wink.

When she returned with Rick, Mark, and Tom’s food, I was halfway finished. Two of the waitresses helped Lynn with the plates. The guys dug right in. I thanked Lynn and the waitresses.

Lynn caught my “thank you comment” and let loose one more salvo, “You can thank me later too, if you like.”

Yes, I caught it. She was now being bolder than before. I had to shift in my seat to allow my cock, now growing from semi hard to full hardness, to have room and not become painfully trapped and having to make a scene to adjust myself. I really didn’t want to do that in front of the guys knowing what kind of ribbing I would take.

Rick couldn’t let it go. “Man! It has to be that shy guy attitude you have. Either that or you have some new cologne or something on. Mark, smell him and see if he smells any different.”

Rick grinned at me as Mark leaned over and made over exaggerated sniffing motions and sounds to the glee of the others. “Nope, smells like fresh soap. Did you just get out of the shower?”

I blushed and shook my head no. I wasn’t about to tell them about my lessons with Abby and the fact that I had really just showered a second time before I left her house. “Like usual, I take a shower before I leave the house. I told you, I ran some errands for my mom. I guess I just don’t stink up the place like you guys do.”

They all chuckled. I kept glancing up to watch Lynn. She checked on us several more times, chit chatting with all of us and always giving me a smile. She dropped off the checks the last time by the table. When we were finally done, Rick reminded us that we would meet up at the Martin’s house and head over to the drive-in just after seven that evening. The movie wouldn’t start until completely dark but we wanted to make sure we’d have the parking area we wanted.

Getting up, the guys dropped a couple of dollars on the table for Lynn’s tip. I had a twenty-dollar bill in my hand with the check that cost nearly five dollars then. They gave me the eye making me uneasy. I responded. “No change. I’ll get some at the counter.”

Lynn was at the register as we approached. “How was your meal, gentlemen?” She actually meant it.

Rick paid first, followed by Mark, then Tom. As they moved to the door to head out, I handed her the check and the twenty-dollars. I smiled at her and said, “I look forward to seeing you there this evening, if you make it. Oh, and keep the change. I enjoyed my meal, thank you.”

Lynn looked at the check and the twenty. She looked me straight in the eyes and said, “Thank you, Sir.” The manager was walking up to her at the register. She mouthed, “Looking forward to seeing you tonight.”

I smiled back and nodded. I know I was blushing.

I met the guys outside as the others began to make their way to the register to pay. I stood next to my Camaro and caught Rick, Mark, and Tom’s attention. “I’ll see you all Mark’s. I’ve got a couple more errands to run.”

I jumped in the car, pressed in the clutch and started the car. The low rumble felt good to hear. I backed out slowly and decided I needed to go home and take a little nap before going out that evening. I drove home with a smile on my face.

**********

I pulled in the driveway and found the garage door open and both cars parked inside. My stepfather walked out the kitchen/garage door dressed in his outside work clothes just as I got out of my car. Seeing me, he smiled and called out, “Just in time. I could use a hand with the lawn if you have some time.”

I waived back and replied, “Let me put on my old jeans and a sweat shirt and I’ll be out to help you. What do you need done?”

The lawn had only had its first two cuttings and didn’t look like it was quite ready to be cut again. “I need to get the shrubs trimmed and put down some fertilizer. Which would you like to do? Your choice.”

Hmmm. I got the option. I knew I could get the fertilizer down faster than he could and I know he would be much happier with doing the shrubs his way. “I’ll get the spreader.”

He responded back, “Good choice.”

I got to the steps and bent down to untie my Converse when my mom appeared at the screen door just as I was bent over. “Oh, you are home. Were you able to drop off the cake pan at the Johansson’s?

I looked up at her and smiled. “Would I let my favorite girl down? Dropped it off.”

I stood up and she opened the door for me. She looked me straight in the eye and smiled before her next comment. “I know she was happy to get the pan in time for tonight’s event. Thank you. I do hope she thanked you too.”

I looked at mom, leaned in and kissed her on the forehead with a nice son-to- mother kiss and responded, “She sure did. I think she’ll let you know how much.”

Mom smacked me on my butt as I tried to slide by her to go and change my clothes. “She already did. She called me with details.” With a second swat, she grabbed my ass cheek and squeezed.

I glanced back at her and smiled as I made my way into the kitchen and out of earshot of my stepdad. I said, “Thanks.”

She smiled. Looking me straight in the eyes, she said, “You’ll get to thank me a lot more later.”

In my room, I just beamed. It only took me a couple of minutes to put on work clothes and I made my way back outside. Mom was busy helping Stan with the hedges, bush trimming and the flowerbeds. I pulled the spreader off the hooks on the garage wall, placed it on the driveway, found the fertilizer, and began my part of the yard work for that Saturday afternoon.

I was done before them. I put everything away and made my way to the down stairs family room. I turned on the TV and didn’t even remember seeing anything before I fell asleep. I was beat.

**********

Mom woke me up for dinner. “Hey there sleepy head. Dinner is ready if you want it.” She had her pink silk robe on, her hair was up and she smelled as if she had just gotten out of the shower, nice and fresh, no perfume or hair spray yet.

I checked out my mom and saw her breasts were free in the robe and nothing on underneath, at least that is what it appeared. As she moved up, her robe loosened up just a bit, her breasts shifting in the silk. She turned and bent over to pick up the two sofa pillows I had knocked off onto the floor. Doing so, I saw her lovely ass, no panties, her pussy lips smooth and looking so inviting. She was shaved as smooth and hairless as Abby. Confirmed, nothing on.

My mom stood upright and smiled at me placing the pillows back on the sofa near my feet. “Well, glad you got some rest. You must have been beat playing all that “basketball” and then fertilizing the yard today. You’ll need that rest for your evening plans. Besides, you’re young. Your batteries recharge pretty quickly.”

I smiled at her and thanked her again for letting me take a nap.

Her response was similar to the one she gave me earlier. “Oh, you will. Later, you will.”

She walked toward the stairs placing one foot on the first step and her hands on the rail showing bare leg all the way up to the top of her hip, the robe slightly open showing her breasts ever so slightly. “And, by the way, while you were taking a nap, Becky Harrison called. I told her you were resting and asked if I could take a message. She said she wouldn’t be able to make it to the movie this evening. She was going to see her grandparents with her mom and dad and wouldn’t be back until late. I guess it was a last minute thing with her mom’s mom. See you upstairs.” With that last comment, she slowly made her way up the stairs.

I glanced at the clock on the wall. It was nearly six. I had to get my ass in gear. I needed to take a quick shower, get ready, and head over to Mark’s house. But first, I was famished and needed something to eat.

I made my way upstairs and mom had set out some spaghetti, home made sauce, Italian bread, and some salad. I made a plate of spaghetti and sauce and placed some salad in a bowl and made my way to the kitchen table. As I started to eat, Stan walked in, no shirt, dressed in just a pair of shorts, having just gotten out of the shower. He noticed my plate and nodded his approval. “It sure does look good. I think I’ll join you. One thing your mom can do in the kitchen is make great sauce. There’s enough there for a couple of meals.”

He made a plate and took some salad and sat down with me.

“Big date tonight?” He asked just before taking his first forkful of spaghetti.

“No, no date. Mom said Becky had called and said she went to see her grandparents with her mom and dad. So, I’ll meet up with the guys at the drive-in. Not sure of what movie’s on. I haven’t checked the paper to see what was playing.”

“Well, don’t forget to drop in and check on the Johansson girls tonight at some point.” He reminded me.

“I won’t forget.” I glanced at the clock and figured I still had enough time to finish my dinner and get my shower.

Mom made her way to the kitchen. This time, I could tell she had on a bra and she had on hose of some sort as she padded softly to the counter to grab a bowl of salad. She turned toward the fridge to peek in and grab a bottle of salad dressing from the door shelf. In doing so, she turned letting the slit of her silk gown separate all the way up her thigh exposing the whites of her thighs, the tops of her stockings, and the white garter belt straps. Stan had his back to her but she let me see her beautiful legs for a few moments before moving to close the refrigerator door.

She reached up and opened the kitchen cabinet that held the glasses. She stood up on her tiptoes to reach for a glass on the second shelf instead of taking a glass off the first shelf. That had to be intentional. Again, doing so, the bottom of her robe rose up to her ass cheeks giving me another great view and showing that she had on a pair of bikini white lace panties along with the lace garter belt.

Mom’s hair was up in the back, held by a few hair clips to keep it off her face and shoulders while she got ready. She had yet to put on her makeup. She ran some water for her glass and brought the salad bowl, a fork, and a small piece of Italian bread to the table before grabbing the glass of water. Sitting down, she took the chair in between my stepfather and myself. We all chit chatted for a few minutes while I finished my dinner and before I picked up my dirty dishes, she placed her hand on my thigh and slowly rubbed it causing the reaction she was looking for, my cock to harden. Well, it did.

I had to turn away from the table to not reveal my raging hard on to my stepfather. I walked my dirty dishes to the sink and rinsed them off. I loaded them in the dishwasher and by that time, I was able to rearrange myself enough to graciously make beg my departure from the kitchen and go take my shower. Stan and mom both acknowledged my request and I began to head back to my room. I passed by mom and she gave me a wink and a smile. I smiled back and took a deep breath.

I showered and shaved in the main bathroom. I got dressed nearly the same as I had been earlier in the morning, but in clean faded jeans and another clean school football shirt. I grabbed a light jacket because it would get colder and damp in the spring evening. I grabbed the old Army blanket from the closet and two pillows from my bedroom. I walked them out to the car placing them in the trunk. I slipped into the front driver’s seat and started the car, made sure it was in neutral, set the parking break and went back into the house. While taking my shoes off, I ran through my mental checklist to make sure I didn’t forget anything. It wasn’t my turn to provide alcohol and I had condoms in my glove box. I was good.

I walked softly over to my mom’s bedroom door and called out, I’m heading out, “Enjoy yourselves tonight.”

Mom came out of the bathroom. She had completed her make up and her hair was now down. She had her dress in one hand still on the hanger and a blue slip in the other. She wore blue stiletto heels, her white lace deep cut bra and white lace panties, garter, and hose. My mom was an absolute knock out.

She smiled at me, winked, and responded; “See you when we get home. If you are home before we are, make sure you take a shower before going to bed.”

**********

I had just enough time to make it to Mark’s. As I pulled onto their street, there were four cars already in the driveway leaving me the street to park. I took note of the fact that I wasn’t the last one to get there though. I walked up to the Martin’s door and as I was about to ring the doorbell, Mrs. Martin opened the storm door for me.

She called out over her shoulder toward the kitchen. “Honey, tell the boys Tony’s here.” She smiled at me and spoke at her normal voice. “I think they are just about ready to go. You can go downstairs and see if they are.”

As I walked in the door, I could hear music coming from the down stairs and saw Mr. Martin on the sofa in the living room just shaking his head and smiling at me. “You guys are quite a group. Reminds me of when we were younger, right Connie?”

The music turned off just as I made it to the stairs and the guys started coming up the stairs. I waited for everyone to reach the kitchen before turning to head toward the door when Mark grabbed his dad’s 1970 Corvette keys off of the family key rack. “Dad, I have the keys to the Corvette.” He smiled at me waiving the keys at me as if to show me he was in charge.

His dad called out in return, “Not unless you want to be grounded for the next month. Take your mom’s station wagon.”

His mom grabbed her keys from her purse and handed them to Mark. “Please bring it back in one piece and clean.”

Mark smiled hanging the Corvette keys back on the rack and gave his mom a kiss on the cheek. He walked out through the garage door and we all followed him out. Once we were all outside, Mark smiled at everyone else before dangling the keys in front of us all. “Guess who can lay out in the back and mess around during the movie in comfort?”

Tom was quick to respond, “Yeah, with yourself.” We all laughed.

Two other cars had pulled up behind mine once we had the garage door opened and Mark got into the station wagon to start it. We were off to the drive-in.

The drive-in theater was half way between our town and the next, just short of the expressway. It took us a whole fifteen minutes to caravan there. We all paid our car fees and played follow the leader to the prime middle spot that had access to the bathrooms and the snack bar as well as easy access to the back rows. We lined up all of us facing forward, side by side, with the exception of Mark and his mom’s station wagon. He pulled up and put the back end out toward the screen. He let down the electric powered back window and got out to open the tailgate for us to sit on. He was right about the car, it was spacious. He had pillows, blankets, an ice chest with ice and sodas. There was even a fifth of whiskey and a bottle of rum in the back seat in brown paper bags.

As more cars began to roll in and it got darker, people began milling around. The screen flickered and scratchy music began to filter through the speakers we had hooked up to our windows. I wasn’t paying much attention when I felt a tap on my shoulder and I turned around to find Lynn standing there.

Lynn looked much different than she did earlier in the afternoon in her hostess attire. Her light makeup was replaced with a little more makeup highlighting her beautiful face. Her luscious full lips were now adorned with red lipstick instead of lip-gloss making her lips so very kissable. Her beautiful blue eyes sparkled with her blonde hair down full around her face and hanging on her shoulders instead of being pinned up atop her head. And, she still smelled so very fresh with her vanilla based perfume.

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I smiled and took a deep breath before making a comment. “Wow! Lynn, you look amazing.” And she did too.

She was dressed in hip-hugger bellbottom blue jeans, a black satin button-up blouse with her band jacket windbreaker, and something I’d only seen on college girls and some women at the mall, high heels with blue jeans. Her heels were black with a three-inch heel, making her legs and ass in the hip-hugger blue jeans look so sexy.

I thought she may have a little trouble walking around on the gravel and pavement combination but she did it and did it well.

She smiled at me and leaned over and kissed me on the cheek ever so lightly. I could feel her breath at my ear when she whispered, “Becky didn’t make it. That’s good for us.” She then took a quick nip at my ear lobe before sucking it between her lips and teeth, tickling it with her tongue, and then letting it go.

I just stood there. Here, a gorgeous senior is hitting on me, I think, and my cock was now trying to snake it’s way around in my own jeans. Yes, I was now getting hard and I was going to have to do something to make myself more comfortable without letting everyone know just how uncomfortable I was becoming.

Lynn looked down and smiled, “Hmm. Interesting.”

I blushed. Seeing she was already watching for my reaction, I turned slightly and shifted myself in my pants, unbeknownst to the rest of our group. Lynn watched and smiled again. “Did I do that?”

We were interrupted with the screen flickering and the pre-movie commercials and promotions beginning. Mark held up two Tupperware tumblers with some ice and asked if we knew what we wanted to drink. I chose the coke with rum and Lynn said she’d have the same. Mark poured much more rum in the tumblers than coke, that’s for sure.

With Mark handing us the tumblers and telling us to enjoy, Lynn and I tapped our tumblers together. I smiled at her and asked, “What would you like to toast to?”

She smiled as her eyes twinkled. She winked and said, “To possible new relationships.”

We tapped the tumblers again and each took a sip of our drinks. Yes, the rum was strong and very little coke. Way to go Mark.

Lynn took more than a sip from her tumbler. In fact, she downed more than half before handing it back to Mark. “Mark, please be a babe and top me back up again. And, a little less coke please?”

Mark was caught off guard. He smiled and poured at least three fingers worth into the tumbler and just waived the coke bottle over it. “How’s that?” He asked.

Lynn smiled back at him and winked. “That will do just fine. And, thank you. Now, Tony, seeing that the movie is going to start here soon, wouldn’t you like to show me the inside of your Camaro so that I can get comfortable?”

I motioned to the car and we began to walk toward it as she took another drink from her tumbler. “You know, the front seats are buckets with the console. I think if I put the buckets forward as far as they’ll go, we’ll be cozy in the back seat.”

Lynn smiled at me as we approached the driver’s side door. “I like cozy, Tony. Don’t you?”

I had to take a very deep breath before answering. I opened the door and finally replied. “Yes, I have to admit, I do like cozy. Especially with someone like you.”

I reached in and pulled seat slide lever pushing the driver’s seat forward all the way and pushed the seat back forward. I moved around to the passenger side door and opened it up and did the same with the passenger seat. I held the door open to see if Lynn wanted to enter the passenger side. She smiled at me and shook her head no. I smiled back at her and closed the door walking around the back of the car to her. She stepped between the open door and the car, put her arm over my shoulder that was holding the tumbler and her other hand went around the back of my head pulling me to her.

“I wanted to do this earlier.” She said. She then gave me a wonderfully deep kiss that surprised me. Although she’d been flirting with me, at least, that is what I thought; I wasn’t expecting that kind of kiss. Her mouth was more than slightly open and her tongue was available immediately. I was sure glad that I had a lot more experience, so to speak, at kissing than I had the day before. My lessons with Mrs. Johansson that morning and afternoon just might have come in handy after all. Go slow, I told myself.

I felt Lynn sigh as we broke the kiss. “Hmm, I liked that. Care to practice some more?” She smiled at me and licked her lips.

I leaned back to grab her tumbler from her hand. “I think I’ll hold this while you slide your way inside.”

Lynn let go of her tumbler and leaned forward to give me a short kiss before leaning into the back seat and sliding over. If you know the back seat of a 1967 Camaro at all, you know it isn’t the roomiest seat but with the front seats up, there was room enough for the two of us to climb in the back and be quite cozy.

Once she was in, I handed her the tumbler. She asked if I had a blanket handy and I shook my head yes before walking back to the trunk and retrieving the blanket.

I handed her the blanket then slid in pulling the driver’s side door closed causing the speaker to clang against the window. I felt like each noise was amplified at that point. I looked over to Lynn to see she was again sipping her rum with very little Coke. Her blue eyes were sparkling. Somehow, the top four buttons on her blouse had magically became unbuttoned showing her beautiful breasts encased in a black lace bra. She still had on her band windbreaker.

“It’s warm in here Tony. Can you help me take off my band jacket, please?” She turned slightly allowing room for me to work the jacket over her shoulders. This gave me another view of her from the side, her full orbs straining against the lace. Once her jacket was off, I tossed it onto the console.

Lynn turned back toward me and slid to the side, leaning over me and across my lap, facing me. She took yet another long pull from her tumbler and leaned forward toward me, my cock now straining in my jeans with her side pressing against me. I knew she could feel my cock pulsing. With her free hand, she again slid it behind my neck and pulled me to her, this time, in an even more passionate kiss than the first.

I could hear the music from the first movie begin and the lights were now out in the drive-in movie lot. Others were mingling around outside as each kiss was more passionate than the last. Abby had stressed how to handle myself with high school girls and I knew I liked what I was feeling and whom I was with. I just didn’t know how far she might want to go. I could have blue balls this evening but I knew, for some reason and regardless, I was going to cum a few times tonight.

In the middle of one of the deep sensuous kisses, I heard a rap on the window causing Lynn to break away and look up nearly the same time I did. It was Tom and Rick and two of Lynn’s friends whom she came to the drive-in with this evening, Brenda and Donna. Brenda leaned into the window and asked Lynn if she was ready to refresh her tumbler.

Lynn smiled up at her and said, “Yes. I could use a refill.” She then sat up and grabbed her tumbler from the top of the console and asked them if they could open the door to grab it from her.

The dome light came on, making us both squint and giving all four of them a nice view of Lynn in disarray. Donna took the tumbler from Lynn and handed it to Tom. “Please be a dear and ask Mark to refresh this. Rum, right Lynn?”

Lynn responded, “Please? “

Donna smiled at Lynn as Tom walked around to the open rear door of Mark’s mom’s station wagon. “Ruthie is in the back seat of the wagon with Mark. We just wanted to interrupt you all seeing that the movie is just about to start. I see you two are becoming better acquainted. Hi Tony.”

"Hi Donna. Hi Brenda,” I responded with a smile. We didn’t move. Lynn chatted with Donna and Brenda as if they were in the hallway at school.

Tom appeared with a refreshed tumbler in just a few awkward moments and handed it to Donna. Donna handed the tumbler to Lynn who then courteously thanked Donna and Tom. Donna smiled, stepped back and shut the door still smiling at us as she turned, grabbed Tom by the arm and they slowly moved back over toward the station wagon.

Lynn smiled at me, took another sip from her tumbler and then put it to my lips for a sip. She giggled and set the tumbler on the floorboard before turning back into me. I wrapped my arms around her as she tilted her head for me to kiss her again when she grabbed my hand and placed it on her breasts. “You can’t just go back to square one and start over.”

She then turned, pulled the blanket up covering us before reaching down underneath the blanket and unbuttoning her jeans and slipping the zipper down. She reached back up to grasp my face in a tender embrace and kissed me deeply again. She then reached for my right hand as I gently caressed her breast and slid it down to the top of her now exposed panties and kept pushing my hand downward as she pushed her hips up to meet my hand. I could feel the heat emanating from her womanhood.

She spread her legs giving me more access to let my fingers slip beneath the panties to feel a closely trimmed patch just right for a bikini. She pushed against my hand as it slipped between her legs. I let my middle finger trace over her mound as she let out a slight moan. She spread her leg open enough to let me slide my finger into the wet folds of her soaking wet pussy. Her juices felt a little different than Mrs. Johansson’s had that morning. While Mrs. Johansson was soaking wet, Lynn’s felt like a silky creamy warm wet sensation on my finger. I split her lips apart and let my fingers wander to her clit. I began to lightly circle her magic button causing her to moan softly, but quite erotically.

Lynn sucked my tongue into her mouth as her body began to shake. I let my middle finger slip into her silky pussy and was immediately rewarded with a deep gasp as she inhaled sharply and a flow of silky fluid greeted my probing finger. I pulled my hand back to try to position it to get two fingers in which caused Lynn’s pelvic thrust forward trying to keep my finger in her. I was successful and slowly slid two fingers into her and was again greeted with a deep gasp as she pushed to help me bury my fingers in her.

Mrs. Johansson, Abby, taught me well. I knew not to rush. Lynn grasped the back of my head pulling me to her tightly and trying to suck my tongue down her throat as I continued to slowly finger fuck her tight and soaked pussy. Her hips kept thrusting on my fingers, fucking them, her sweet nectar dripping down.

Lynn moaned and then she began to mumble as her body began to shake, “Oh fuck, fuck, fuck!”

She clamped her thighs on my fingers as her body continued to shake with my fingers still buried deep in her. I learned that Abby could come multiple times, but Lynn, on the other hand, just had a massive climax and was now so sensitive and needed to take a break from further sexual stimulation. Any movement I made with my hand or fingers caused her to shake, shiver, and moan. It took me two minutes to slide my fingers from her pussy as she took in the euphoric feeling she had just encountered. My cock was throbbing in my jeans, but the look on Lynn’s face was priceless and I just took it in.

“Oh! My! God! Tony, what did you do to me? I’ve never cum like that before, whether by my own fingers or with anyone while heavy petting. I’m still buzzing down there.” She was gazing into my eyes and kissed me again deeply before letting me respond.

I considered Lynn’s comment as very informative. I noticed she said “heavy petting” and didn’t say the words “fucked” or “made love to“ in her comment. “All I can say is, WOW! You are very orgasmic.”

She turned with her head in my lap and having left her jeans wide open and nearly now off her hips, she reached back and unclasped her bra, then grabbed my hand and placed it on her breast. She maneuvered herself to get into a position where she could unbuckle my belt, then my jeans before slipping down the zipper. Now it was my turn to moan softly as she let her fingers trace my throbbing cock through my underwear before trying to wiggle them down. I shifted myself and helped her slide my jeans off my hips giving her access to my cock, which by now, was straining and throbbing before her.

Lynn pulled the blanket to cover herself as I felt her breath on my cock as she got closer to it. She grasped it with both hands and studied it before giving the head a sweet kiss. It was nothing like how Abby had sucked my cock earlier in the morning but Lynn was so intent on studying it, as if it was the first cock she’d seen. Then she told me.

“Oh fuck Tony. Your cock is the first one I’ve been this close to with any guy I’ve been out with. Usually, they’ve already cum in their pants from trying to finger me or came when I placed my hand on their package still in their pants. This is the first hard cock in my hands. It is so hard. I feel it throbbing. Please, please, please let me know if I do anything wrong.”

She then let her tongue slide over the tip and then she lowered her mouth down the shaft of my cock. She softly exhaled as she took me in and then let her lips form that wonderful seal on my cock before she softly began to suck and stroke me. She was no Abby, a skillful teacher and lover, but she was so damn cute and had my cock in her mouth at the moment.

I let my head lay back against the seat as she studied and learned her way around my cock. I let my fingers of one hand gently glide through her hair, as the other was busy cupping her breast and playing with her hard pencil eraser nipple. At least ten minutes passed before she let my cock go with a plop and looked up at me with those beautiful eyes and asked, “Am I doing something wrong? Is there something wrong with me?”

“Oh my no,” I softly answered back. “Why are you asking? You feel wonderful.”

“Because you haven’t cum yet. My mom and my friends said all guys cum in less than a minute. And so far, my experiences, limited as they may be, it has been less than a minute and they haven’t even gotten it out of their pants. Are you sure I’m doing it right? You would tell me, wouldn’t you?”

“Oh God Lynn. Yes, you are doing it very well and no, you aren’t doing anything wrong. You are awesome and the feeling is wonderful. I’m thoroughly enjoying it.”

“Really?” She kissed my throbbing cock again and sucked it once before continuing. “I’ve never sucked a cock. I’ve only read about it in some of my mom’s smut storybooks I found in her closet and we girls have talked about what we would do given the chance. Your cock feels so good in my mouth. At least the books were right about that and the girls all wish they could have this kind of experience. I’m afraid of what happens when you do cum, if it’s like the books said or if it’s like the stories the girls tell. Of course, none of them have actually gone that far yet.”

“Lynn, you are the first girl I’ve been with past second base let alone this far.” I wasn’t lying. Abby was a woman and I’d only been to second base in my attempt to get my hands into Becky Harrison’s panties before today. “I don’t know what happened to those guys before.” Yes I did, but Abby’s lessons paid off at this point. “You feel wonderful. And, I’ll let you know when I’m ready to cum. You can decide where you want me to cum.”

Lynn batted her eyes before taking a deep breath as she continued to slowly pump my cock with her hand. She looked me straight in the eyes and responded, in a matter of fact tone, “Oh, I’m taking this. Mom, you don’t know what you’ve been missing. This boy’s cock is nothing like what you told me to expect.”

So far, we hadn’t seen a single scene of the movie. Lynn continued to tease my cock and treat it as if was her own Popsicle and waiting to see if there was a golden prize inside. She got into it and at one point, got up on her knees with her hips moving, fucking the air. She was so into giving me head that she was near another climax herself. She slipped her hand between her legs and soaked her fingers in her pussy. She drew it out and slipped her fingers into my mouth. I sucked and licked all of the juices off of her fingers, sending her over the edge again.

I really had no concept of time but I knew at that point I couldn’t last much longer and let her know how close I was just as her body began to shake. I grabbed her head gently with both hands and began to pump my cock into her mouth. She locked onto my cock and then mumbled as she let my cock escape from her lips for just a moment. “In my mouth. God, yes, in my mouth, please. Cum in my mouth for God’s sake.”

She sucked me deep again and I felt the cum rise from my depths and let go of four good strong ropes, the first of which nearly gagged her but she was relentless and hung in there to take the other three.

My cock remained hard as she shifted to release my throbbing member from her mouth and look me in the eyes. “Holy fuck! That was amazing! A little different in taste and texture than I thought it might be but, oh the feeling of you cumming in my mouth. I swallowed it all.”

“Lynn, that was amazing. My first.” Like I said earlier, of course I wasn’t going to spill the beans about earlier in the day but she was my first high school girl, and yes, she was amazing.

The movie music coming from the speaker was loud at this point. The windows were pretty fogged up and the car smelled of sex. Well, of Lynn’s pussy juices. Lynn had a glow about her. She was so lusciously erotic as she shifted to sit up, her firm breasts free of her bra, shirt completely open, and her hip hugger jeans over her ass; Wow! Even though she wasn’t actually “freshly fucked”, she had that glow about her.

“Oh my God, I loved it. Your cock, your cum. Did I really do ok?” She smiled at me looking for my approval again.

“Yes, yes, yes. I can’t believe you haven’t done that before. “And really?” I asked. Those other guys never made it past their own underwear?”

She looked so damn sexy looking at me. “Tony, I’ve only been with five guys past a kiss. I’ve had them fumble with my tits and having problems with my bra where I had to take the lead. Then, one guy kept running his fingers over my slit through my jeans. I felt wet but all of a sudden, he came in his pants and the date was over. Let’s just say, I hadn’t had much luck up to this point. And, so you know, they didn’t get hard again. They fumbled around like they were scared or embarrassed to be with me and ended the date. You on the other hand, your cock is still hard.”

Her hand slowly kept stroking my cock. “I’m still hard because its you. You do this. Besides, I never ever would have thought you would want to have anything to do with an underclassman like me.”

“I’ve wanted you to ask me out for quite a while. You seemed to always be more interested in Becky than me. Today, I took my chance. I’m glad I did.”

Lynn finally released my cock. She reached for her drink and took a sip before handing it to me. We chatted for a bit and in no time, the movie credits were rolling. Cars started their engines and headlights came on.

We both scrambled to get ourselves presentable, zipped and buttoned up. Lynn began to brush her hair out when the driver’s side door opened on Mark’s mom’s car. Ruth emerged, her hair frazzled, the buttons on her blouse didn’t quite seem right as if they were not quite matched to the right buttonholes. Mark climbed out behind her adjusting his pants and running his fingers through his hair.

I smiled at Lynn, “It seems Ruthie and Mark may be an item and maybe, just maybe they got past second base.”

Lynn kissed me on the cheek before providing her response, “If it were up to her, she’d have four kids with him and never let him out of her sight. She says he’s going to be a doctor and doctor’s wives do pretty damn good. But, they haven’t gone all the way yet. And as of tonight, I’m the first one to suck a cock to completion. Oh, and I swallowed.” She had a very cute grin at that point and her blue eyes twinkled.

I reached for her band jacket before turning to open the driver’s door. The Camaro’s back seat area is small, but we did make the most of it. I slid out and reached in to help Lynn climb out. She reached back for her tumbler and again gave me another kiss. This time, deep and sensual, with her tongue wrestling with mine. “Becky doesn’t kiss like that, now does she?”

“Lynn, you two are in two different leagues.” I pulled her tight before moving to help her into her band jacket.

“If you can find your way to my house tomorrow afternoon, like four o’clock, we will have a lot of time to ourselves. Maybe, you can take my virginity then. That is, if you can last like you did tonight. Oh, I’m on the pill. So, don’t worry about that and don’t bring a condom. I definitely will not let you use it.”

She handed me a piece of paper with her phone number and address on it. I just stood there, amazed. How was this happening? For my whole sophomore year, I couldn’t get past first base and maybe getting a slight feel of Becky’s tits then in one weekend, no one day, I lose my virginity to my mom’s best friend and get head from a senior and now an offer to take her virginity the very next day.

“I’ll be there. I would love to take you home now if you would let me.”

She gave me yet another kiss and grabbed my cock. “No, we’re having a sleepover at Ruthie’s house. We girls have some chatting and catching up to do.” She grinned at me and headed towards the girls’ car. She looked over her shoulder, waived and yelled out, “See you tomorrow.”

The second movie was a B horror movie with some no name actors at the time. In fact, I don’t even recall the name. I walked over to Mark and the guys, all of which were ready to leave and head to Mark’s house. I waved them off and told them I still had to check on the Johansson girls before heading home. I looked at my watch and it was eleven o’clock. I made my way to the Johansson’s to check on the girls.

As I pulled into the Johansson driveway, both girls were at the front picture window waiting for me. The front door opened just as I put my hand on the door handle. Both Brenda and Tammy were smiling and grabbed my hand to pull me in the house. Just as I stepped in, the phone rang. Brenda ran to grab the kitchen phone and answered it as Tammy dragged me down the hallway towards the kitchen, barely giving me time to close the front door.

Brenda handed me the phone, “It’s mom. She says hello but wants to talk to you.”

I took the phone from Brenda as she watched me intently while Tammy hung onto my waist. “Hello.”

Mrs. Johansson’s sensual voice came on the line and I could hear dance music blaring in the background. “Tony, I sure do hope you got some rest today. Are you just getting there?”

“Yes Ma’am. I did, and yes, I just literally walked in. I was at the drive in with the guys.” Brenda smiled at me and Tammy kept grinning.

“Your mom said you went with the guys. Did you get to have, I mean, see that Becky Harrison girl?”

I must have turned three shades of red at that point. Brenda noticed it right off and her mom sensed it in my hesitation to answer. Finally, I responded, “No, she went out of town with her parents to see her grandparents tonight and will not be back until late. I only stayed for the first show and came here to check on the girls.”

“Well then, don’t you stay there too late, you hear me? You need to get home and get a shower and be in bed by one. Nothing on, you hear me?”

I just stood there. A pregnant pause filled the air. Then I responded. “Ok, you don’t want me to be here when you get home then?”

Mrs. Johansson responded, “No. You need to be home. I think you’ll like what you get tonight. Oh, and I’ll see you tomorrow at eleven. We’ll have some catching up to do then. Bob and the girls will be back at his brother’s house and he should be gone by ten thirty. Oh, and another thing, your stepfather will not be home tonight. He’s occupied and should be home tomorrow morning sometime. Bob and I will drop your mom off. All is good. It will even be better. Tell the girls to be good. See you.” Then, the phone went dead.

I handed the phone to Brenda. She saw the look on my face and as she hung up the phone, she asked me, “Are you Ok Tony?”

I smiled at her and nodded yes. “But, I can’t stay long. I have to be home in about thirty minutes. So, is there anything you two need this evening?”

Tammy laughed and began to tell me about the funny Abbott and Costello movie they watched and Brenda said they were ready to grab their blankets and camp out down stairs. I walked down with them and made sure they were all tucked in before heading home.

I was home well before midnight, in and out of the shower, and climbed into my bed. I didn’t hear my mother come home or in the door. I didn’t even hear her make her way back to her bedroom or her shower run. What I do remember is I woke up with my mother standing at the side of my bed, black garter belt, hose, black heels nothing else on. Her hair was cascading down and she had both hands on my throbbing cock, leaning over watching it intently as I opened my eyes and focused on her, taking in her beauty. “Abby tells me my little boy isn’t so little after all and became a man today. By the feel of this, she’s so right. Care to show me what you learned?”

She let go of my cock and slowly strutted to the door. She looked over her shoulder and called back to me, “Follow me. We need a bigger bed than that.”

I got up and followed her into the master bedroom. She lay there, in the middle of the bed, one leg up slightly and legs spread motioning to me with a “come here” finger move, lusty eyes and a soft, “I loved what I had my hands on in your bedroom and oh my yes, you have grown baby.”

 

To be continued in Part Five

 

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Written by EnjoyBoth
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