It has been five months since Megan has become my full-time assistant. She kept with her plan and it is taking a class a term at the local community college. One evening there is a knock on our door as we are finishing up dinner. At the door, I find Megan’s younger sister Ginny. It is obvious that she has been crying for at least the entire mile walk up to our house from her place and probably even longer.

“Megan you better come over here right away and help your sister” I call out. “Come in Ginny, what’s wrong?”

Megan comes running over and giver her sister a big hug and leads her into the kitchen and half closes the pocket doors. I can hear bits and pieces of the conversation, like “Bobby Kirkpatrick is a BIG JERK” and “I HATE BOBBY” shortly followed by “Cindy is even worse, that two-bit slut”. In a little bit, I see Megan rushes out of the kitchen, grabs a box of tissues, and hurries back in.

After an hour or so of consoling her sister, Ginny has calmed down enough that the girls are putting their coats on. “I am running Ginny home Kyle, be back in a bit” When she gets home, she slumps in the chair next to me. “Ugh, why are boys so stupid?”

“Ginny having boy problems I take it?”

“Yeah, typical high school boys. Ginny was dating Bobby and caught him cheating on her with Cindy. Of course, he denied it, but today she learned that Bobby is taking Cindy to the school dance on Friday. She is just a total mess right now. And she is getting all self-conscious about her body that she is going to turn out like our aunt, tall skinny and with a flat chest.”

I could tell there was something more on Megan’s mind than Ginny. She looked down. I move over and sit on the arms of the chair and put my arms around her. “What’s wrong, babe? Something is on your mind more than Ginny I can tell.”

“Nothing. I’ll be fine” and she gets up and walks out. Fine my ass I think to myself. But I am smart enough to keep my big mouth shut.

As I get ready for bed later that evening, I notice that Megan went down to her apartment, and has been in there hardly making a peep. I start to think I am sleeping alone for the night, but then the door to my room cracks open.

“Can we talk?”

“Of course, babe, come in.”

Megan climbs into bed and motions me to get in with her. “Hold me” she whispers. I set up with my back leaning up against the backboard of the bed and pull her in close to me, my legs spread apart to get her close as possible. I wrap my arms around her. Megan emits a soft purr.

“What’s on your mind?”

“Us, I so wanted to tell Ginny that things get better when you get out of high school. When you start dealing with men and not boys.”

“Not all men are good Megan, you know there are some class 1 jerks out there.”

“Those are not men. Real men treat women with respect. That is why I like you, Kyle. You are a real man; one I could take home and be proud of.” She reaches up and back and strokes my cheek. “I want to tell my parents about us, Kyle. What do you think about that?”

“How much about us?” I say a bit nervously. “I am not sure how well your dad will take it.”

“I’m not going to tell them everything silly. I was thinking of treating it like we were thinking of starting to date. And I will start with mom. She’ll know how to deal with dad.”

“Good idea” I lean over and give her a kiss on the cheek and a big hug. “you ready for bed?” Megan reaches over and turns out the light. We snuggle down together.

“Thanks for not trying to do something tonight, I am just not in the mood.”

“I know, I can tell you are not up for anything. Some days are like that.”

“You are so awesome, such a gentleman. Even though you are UP for something, you don’t push it”

I chuckle, “It’s HARD not to be UP for something when your panty-clad ass is rubbing against my cock.”

“You booger, now go to sleep”

I hold Megan in my arms, and we drift off to sleep.

I wake up as the light starts to pour through the window and notice my morning wood. I am not the only one who notices it. There is a pair of hands working to free it from my boxers. Megan starts to gently stroke my dick and plays with my balls. Tenderly she moves her lips over my head, and I begin to feel her tongue circle the head of my cock. It doesn’t take long and ropes of cum begin to shoot down her throat. “Nothing like your boyfriend shooting his spunk down your throat to start your day off right.” I couldn’t agree more, noticing, however, this is the first time she used the word boyfriend regarding me. ‘Are we an item?’ I think to myself. We both climb out of bed to start the day.

That night at dinner Megan tells me how she met her mom for coffee. “I told her I have a problem, a boy problem. She was like ‘isn’t Ginny enough?’ I told her that it wasn’t that type of boy problem. I said I had met a nice man, who appears to be kind and gentle and is a real hunk. But I was unsure how he felt about me. I think she suspected it but did a good job feigning surprise when I told her it was you. I mentioned that I was not sure you were ready for a relationship yet and was concerned that If I brought it up, I might put my job at risk. Her suggestion was, that if I was interested, and was sure I wanted to try, I should drop a few hints and gauge your reaction.”

“Not a bad suggestion” I replied.

Later that week I was out for a walk in the neighborhood. I was deep in thought about Megan and me, and heard “Hi Kyle….Hello…Kyle are you there???” I snap out of my thoughts and realized I was walking past Megan’s house. In the front yard was her mom, Michelle, weeding her flower bed.

“Oh, hi Michelle. How are you? Sorry, I was thinking about stuff and was sort of blocking out the world.”

“Big important thoughts I’m sure”

“Yeah, say can we chat a bit?”

Sure, why don’t you come in the house with me, I could use a drink and break.

We head inside, where Michelle pours a couple of glasses of Iced tea. “So what’s on your mind”

“Megan”

“Oh, I see. What’s going on? Is she in trouble?”

“No quite the opposite. I think I am the one in trouble. How do I say this….hmmm….well, I don’t do so well with tact at times, I am more of a straight shooter, which does me well in business, but not so well at times with women…”

“Go on, it’s ok”

“Well, I am finding myself attracted to her and I am trying to figure out what I should do. I am not sure what she thinks of me and the last thing I want to do is scare her off and lose my assistant. There are moments lately when I think she might be flirting with me, and other times she is just all business. And I am not sure she would want to be hanging out with someone so much older than her. Oh, what am I doing, I shouldn’t be talking to you about this. Sorry, this is very inappropriate of me.”

“That’s ok Kyle. I don’t think you should have much to worry about. In fact, Ginny thinks Megan is sweet on you. I’m not sure, but Ginny knows her sister better than anyone. Take it slow, you are not in a hurry.”

“So you think it would be ok if I asked her out on a date?”

“Yes, Kyle, Scott, and I have been wondering if something like this might happen for a while. I like you a lot and respect how you treat Megan. You are a good man. Scott has the same opinion.”

That’s a relief I think to myself. “Thanks, Michelle, I had better get going. Thanks for the iced tea.” I head out the door and head back up to the house.

“Megan, guess who I talked to on my walk” I announce as we came in the house. “your mom was working in her flower bed and we talked a little bit about us. I think we can slowly begin to be seen dating.”

“Great, so where you are taking me Friday night?”

“Wow, not wanting to waste any time I see. Let me see if I can get a reservation at the Cove House on this late notice. They are normally booked solid weeks in advance, but they owe me a favor for some repairs we did a while back.”

“Sounds like a plan.”

It was hard to wait until Friday. I was able to get reservations for the two of us. Finally, the day arrived. As soon as I got home, she disappeared down to her room and was in there for an hour and a half before it was time to go. Just then Megan came upstairs. My jaw dropped and I hear myself say “Holy Shit Megan, you look great.”

That was the understatement of the night. Megan was wearing a tight-fitting knee-length black dress with spaghetti straps. The dress barely covered her DD-cup tits. Her hair had a small French braid on either side pulled back and was holding the rest of her blond hair that was curled into ringlets. Her makeup looked like it was professionally done. A nice pair of black sheer stocking and 4” inch pumps complete the outfit. With her was another girl I did not recognize.

“Kyle, this is my friend Nicole, she works at the spa and salon by the mall and helped me with my hair and makeup. You like?” The wide eyes on my face and the matching grin was all the answer she needed. I let the two girls giggle for a bit while I went to my room.

As I left, I heard Nicole whispers into Megan’s ear “so are you going to fuck him tonight?”

“Nicole!” Megan exclaims with a fake shocked voice. “Not on the first date.”

“First date my ass.” The girls giggle. “I know you better than that. Go have fun. I’m happy for you both.”

I came back with a small wooden box. “Here, I think you should wear this tonight with that.” Inside was a gold braided necklace and pair of earrings that had two strands of a matching braid than hung about an inch down. At the tip of each braid was a small diamond.

“Oh Kyle, I can’t”

“Oh yes, you can sister” Nicole cut her off. “These are gorgeous. Let me help you put them on.”

I stood there admiring Megan. This was not the sporty casual babe who I normally see around the house, but a sexy woman.

On arrival, we were told our table would be ready in 10 to 15 minutes, we were a bit early. We walked out onto their patio overlooking the cove marina. We found a quiet corner to watch the world go by. I wrapped my arms around her from behind. I reveled in the smell of her perfume and the softness of her body. It was hard not to let my hand wander over her body, but I had to remind myself we were in public. Megan began to caress my arm. She turned around to face me, with my arms still wrapped around her. I felt her lips touch mine and we embraced. I just wanted to freeze this moment a little bit longer and make time stand still.

As we headed back into the restaurant, I could see a lot of eyes checking Megan out. I got a couple of discrete thumbs up from a couple of men, who wished they were me. And since she looked more mature than her age, the wine steward just winked at me and brought a nice bottle of French red wine he recommended to us to go with our meal.

While we were waiting for our dinner, Megan slipped out to use the lady’s room. When she got back, she had me stick out my hand under the table. Next thing I know I have a wet pair of satin panties in my hand. There was a twinkle in her eye and smile, “You’ll have to see what those go with later babe.”

“I’m going to have a hard time leaving here babe. Everyone is going to see that you have given me a problem in my trousers.”

“Good thing I am a problem solver, I have a feeling everyone will still be looking at me as we walk out.”

And she was right. The valet captain could barely keep his eyes in his sockets on our way out. She made sure to hike her dress up a bit as she got in and spread her legs a bit to give him a quick peep at her pussy as he held the car door open for her. After we pulled out of the parking lot, Megan started to laugh. “Did you see the look on the valet guys face? That was Jimmy Helms, we went to high school together. How much you want to bet he pulls out his yearbook and jacks off thinking about me tonight?”

“I ain’t taking that bet. He almost creamed his pants on the spot checking you out.” I had a hard time keeping my eyes on the road the rest of the way home.

I walk out of the kitchen carrying two glasses of red wine. I lead her back to the master bedroom and instead of turning on the lights, I turn on the gas fireplace and pull her down to me on the floor. The firelight catches the diamonds in her earrings and accents the smile on her face. The makeup has hidden her freckles, but nothing can hide her dimples. I reach up and gently brush her face with my hand. Megan shudders. Out lips draw close, she opens her lips to let my tongue in. I start to move my hand down to feel her ample breasts, but she stops me. Slowly she stands up and with a couple of flicks of her finger, the spaghetti straps from her dress fall off her shoulder.

“Pull it down” I don’t need to be told twice. I gently tug at the hem of her dress just above her knee and the dress is off. Underneath a gorgeous dark purple strapless corset with black lace is revealed. Her sheer black stockings are being held up by a pair of garters coming from the bottom of the corset. I have never seen a piece of lingerie that fits a woman so perfectly in real life. Utterly amazing.

“Wow,” I breathe. “I am almost speechless. It’s beautiful on you.”

“I thought you would like it. I know you have a bit of a lingerie fetish.” I marvel in her glow, not just the glow from the fire, but one of confidence and lust emanating from deep inside this young woman. She does a bit of twirl around for me. The sight of her blond curls floating in the air was enough to give me a stiff one, but that point was reached a long while ago. Not only does the firelight dance off the gold necklace and earrings but shimmers off the purple satin of the corset. I can see a glint of moisture dripping from her trimmed pussy.

She extends her hand and pulls me up from the floor. I had taken my suit coat off when we came in the house, so Megan is free to begin to unbutton my waistcoat. She notices the bulge in my trousers and sees that it is in an awkward position and reaches down to my groin and gives me a bit of shift. Megan pauses to unbutton my shirt but decides to rub her hands over my chest. They move back to my ass and she pulls me tight to her body. The feel of her tits pressing into my chest causes me to breathe a bit faster. Meantime my hands are slowing rubbing up and down her backsides. I massage her firm butt cheeks and then move a hand between them. I gently massage her rosebud a moment and then move my hand underneath her. I rub two fingers around her outer labia. Gently making a “V” shape on the outside of her mound.

I rotate the position slightly so I can reach my hand down from the front. My hand gently massing her entire vaginal area. My first finger slips in so easily that I slip a second one in as well. We embrace as I move my fingers in and out. I curl my middle finger forward and find her G spot. Megan starts to suck on my lower lip. With one hand wrapped around her and the other fingering her, Megan starts to buck her hips on my hand. Her body starts to go limp and her eyes roll back a bit.

“Mmmm Fuck yes Mmmmm don’t stop Ohhhh yes fuck yes fuck fuck fuck fuck OHHHHHHHH”

Her body explodes with wave after wave of her orgasm coursing up and down her 5’2” frame, now 5’6” in her heels. She grabs me tight, so she doesn’t fall over. I hold her tight to help her recover. She gives me a big kiss and steps back to catch her breath some more.

“That…that was amazing. Wow…. oh my, did I do that?” She says pointing to my left leg. My trouser is soaking wet along the thigh and down to below my knee.

“Yep, you squirted all over me,” I say proudly. It was the first time I had made her squirt.

“I never did that before, didn’t know I could. I heard about squirting but never did it.” Megan helps me out of my wet trousers and the rest of my clothes. I place each hand on her ass and start to lift her up. She gets the clue and throws her arms around my neck and wraps her legs around my waist. I carry her across the room, my cock gently rubbing her hairy pussy. I softly lay her on the bed, her legs hanging over the side. I raise them and place them on my shoulders and press the head of my cock against her womanhood.

“Mmmmmmm fill me up, fuck me please” I oblige, her soaking moist pussy practically pulls my cock in. One thrust and I am in all the way. “I love your cock, I love how it fills me up. Take me”

I start to slowly move my hips back and forth. Megan purrs like a kitten, my hands wander to her tits. “Faster, deeper please… oh don’t stop…fuck me…yes… oh yes fuck me Kyle” Megan is gripping the side of the bed and my hips go faster. She squeezes her legs tight around my neck, and her tight teen pussy gets even tighter. Her back arches and her body begins to shake. Yelling out with pleasure, her pussy released a jet of squirt all over my cock and groin. This pushes me over the edge and a torrent of seed fills her cunt. I pull out and my body flops onto the bed next to her. After a moment she rolls over on to my side and cuddles. I begin to play with her curls.

“Gentle babe, I don’t want you to rip them out.” I give her a bit of an inquisitive look. “Hair extensions, my hair is long, but not long enough to do all these curls. You like them?”

“Fuck yeah babe, you are so beautiful tonight.”

“Thank you” she kisses my lower lip and her hand explores my jaw. “I’ll take them out later when we are done.” My eyes widen and I smile. She smiles back, “You ain’t done yet, mister.” She reaches down to my semi-hard cock. “There are going to be multiple shots on goal tonight. But first I think we both need a break. You mind get me a glass of ice water.”

How am I to refuse. I kiss Megan on the forehead as I head to the kitchen. I pause in the hallway on my way back at a photograph. Staring at it I break into a small smile. Still holding a glass of water, my index finger traces along her face. “Thanks, I still love you as well.” As I stand there a hand reaches out to hold the glass of water. I look over and a now naked Megan is standing beside me. Her other arm is wrapped around my waist. She is also looking at the redhead on the wall. “I’ll take care of him, Emily, I promise.” We walk back down to the bedroom. The firelight still filling the room, we crawl into bed.

This time Megan is holding me. She softly says “Thanks for being so caring and letting me be in your life. I know you will always love Emily but thank you for making room for me.”

“A wise woman once told me that your love does not replace one person with another, but your ability to love grows as more people enter your life.”

“Emily was a wise woman.” I nod my head.

There was silence for a few minutes as we just held each other. “I am such a lucky guy to have met two beautiful women in my life.”

“Ok, I can take that,” she says with a smile. With that, she reaches down and grasps my cock. “Let’s see what you have left.” With that, she wiggles around and puts my semi-erect penis in her mouth. I’m hard in no time. She motions me to lie flat on my back and carefully spread her meaty pussy lips, so they drape on either side of my cock. Her juices lubricate my cock further and she glides her pussy up and down the length of my cock. It is all I can do to keep from coming right then and there. After another moment, she lifts herself a bit, and with her left-hand pushes my erect member into her pussy. The feel of moist pussy is so good. I enjoy each squat she does on my cock. My hands-on her ass helping to lift her up and down. I think I can still feel some sperm from my first load in her vagina.

I lift her off me and roll her onto her stomach. I come in behind her and slip my shaft into her pussy from a prone position. Draping my body on top of hers I resume thrusting. My hands grasp her shoulders keeping my body tight to hers. Her moans indicate that I must be hitting her G spot again with my cock. I feel her body tensing again and then erupt into another orgasm. Shortly thereafter my cock explodes again filling her with more spunk.

After we recover, she slips out of bed and heads to the bathroom to pee. I head in a little bit later and find her wiping the makeup off her face. The hair extensions are lying on the counter.

“You did look magnificent tonight Megan.”

“Thanks, it was not all me though, Nicole helped.” She stands in front of the mirror brushing her hair. “Yup, we were besties in high school. She went to cosmetology school but wants to be a photographer. She is saving up to start a studio of her own. Her dream is a lingerie store and boudoir studio in one. She was down in my room when you came home and helped me when I went down. I had her park her car down the street so you wouldn’t notice.”

“You are a sneaky woman Megan.” I kiss her. With that Megan walks into my closet and pulls out my football jersey. Slipping it on, she cuddles up to my naked body in bed. Her bare ass wiggles against my erect cock.

Megan turns out the bedside light and cuddles back into me. “Sweet dreams babe.” All I dream about is the cute blonde in my arms that night.

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