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The Boss, The Mom, And The Daughter

"A Thanksgiving Break Triple Play"

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Author's Notes

"For background, I suggest reading the whole series. But, this is more specifically a follow up to Mom’s Princess Visits Campus."

The week before Thanksgiving break was a blur. Classes ran until Wednesday morning. Fortunately, Fall baseball practice was light that week, with no practice on Wednesday through the following Tuesday. The Monday after Thanksgiving in Pennsylvania is a State Holiday. So, all state-sponsored schools, elementary through colleges, incorporate that Monday into the Thanksgiving breaks. The holiday is for the first day of deer hunting season. So essentially, my break began Wednesday afternoon and ran until Monday night.

On Monday morning, I called Donna at her legal office to find out her Thanksgiving plans. When she visited campus in September, we had talked about our likely next rendezvous occurring during my Thanksgiving break. (See Donna Visits Campus for the details).

It turned out that she and her daughter, Lynda, would be going out of town to Donna’s mother’s place on Wednesday. They would be spending Thanksgiving with family and coming home late Friday. Saturday morning, Lynda would be going to her Father’s home for the rest of the weekend, returning home on Sunday afternoon. So, we made plans for me to come to Donna’s house on Saturday for dinner.

My holiday plans were basic. Spend Wednesday evening and Thanksgiving with my family. Spend Friday evening meeting up with old high school friends at a local bar known for honoring fake IDs, Alfies, which was just outside of Reading. Saturday evening and Sunday morning would be “Donna time.” Sunday afternoon would be football time with family. Monday, I would make the 3-hour drive back to campus.

Thanksgiving break finally came. After fighting the holiday traffic on Wednesday, it was good to just relax at home and catch up with family. Thanksgiving Day included the standard festivities. Play in the local pickup football game, eat a feast, and nap through football on TV.

Friday started with the watching of the big annual rivalry college football game between my school and that other school from western PA. Our motto toward them was “Shit on Pitt.” And, we did. This year's contest was a blowout.

Friday evening, I headed to Alfie's. Alfie's was a standard local PA bar that was located near a nursing school and three small colleges. It was also a place where college kids, who were home from school breaks, gravitated to. This was due to a quite liberal reading of the many fake IDs used to circumvent the twenty-one-year-old drinking age.

I spent most of the evening catching up with old friends talking about the ass whipping we put on that western PA school. I also picked up some good intel for Monday.

One of my old high school buddies caught wind of a house party that was going to occur Monday afternoon by the guys on our high school’s basketball team. As was standard back then, practice would be early in the morning to accommodate those players who wanted to deer hunt later that day. So, the party would start at 2 PM. The parents would not be home as they were at the hunting camp until Tuesday night. As this party would be on my way back to school, I figured I would stop by and check that out before heading to campus.

Later that evening, while making my way back to my table, I heard a familiar female voice say, “Lefty, when did you turn twenty-one?”

I thought, “Oh shit! I am fucked!”

The voice was that of my assistant manager at the ACME grocery store where I work during my Christmas and summer breaks. I figured she likely knew I was teetering on being twenty-one, but I didn’t want to lie to her. So, I turned and said, “Hi Deanna! Funny running into you here. This is typically a college hangout place on a Friday.”

Deanna was about forty-eight. She was about an inch taller than me at 5’11”. She was sleekly built with long legs and a nice rack. Deanna was a dancer and still teaches dance in the community.

Deanna replied, “I know, Lefty. I live about a mile from here. I also know that about half of you twits are likely in here on a fake ID, like I used to do, when I was your age.”

Then she winked and said, “So, I remember we did a birthday celebration for your twentieth last August, right before you headed back to school. Your secret is safe with me.”

We both laughed, and I offered to buy her a drink. We stood and chatted. It turned out that her husband left for the hunting cabin early this morning, and Deanna was supposed to meet her cousin at Alfie's. Her cousin showed up, had a quick drink, but she had to leave early because she had a sick kid at home that she needed to get back to.

Deanna and I stood and talked through three more drinks. Deanna wanted to sit down, but there were no seats available. I said, “Well, I have had about enough of the cigarette smoke anyway, we can go out and sit in my car if you want?”

Deanna smiled, laughed, and said, “Is that your standard pickup line, Lefty?”

I smirked and said, “Is it working?”

We headed out of the bar to my car, which I conveniently parked on the back corner away from the road and any lights. One never knows if they might score a young horny nursing student at Alfies. This parking lot is a voyeur's delight at closing time.

November evenings in PA are quite chilly. Neither of us had coats on, so I turned on the car to put on some heat. We continued to chat and Deanna looked at me and said, “Lefty, I haven’t been with anyone but my husband for over twenty-five years. But, he and I haven’t had sex in over a year. He has gotten fat, lazy, and just gets drunk most nights. I am lonely. I didn’t come here to have a hookup. But, I think I am interested in having some fun with you. But you probably have no interest in an old lady like me. I am more than twice your age.”

I replied, “Deanna, you are a beautiful woman.”

I leaned in and kissed her. We broke the kiss. I kissed her again, and Deanna opened her mouth as I pressed my tongue to her lips. Deanna softly moaned into my mouth. I broke the kiss and whispered into her ear, “Should we take this to your place? This parking lot will soon be crowded with people leaving the bar.”

Deanna replied, “I have too many nosy neighbors. We can’t go there.”

I kissed her deeply again and started to lightly rub the side of her neck. I then whispered into her ear, “I know where we can go. There is a baseball field not far from here. No one will bother us there. Do you want me to drive there?”

Deanna nodded yes. The park was less than a ten-minute drive. It was very dark, and I parked next to the storage building. When we parked, I left the engine running so that we could have heat. We moved to the back seat so that we would have more room. We began to make out. My hands roamed Deanna’s body, which was firm and tight. When I rubbed her ass over her jeans, she cooed into my mouth.

Deanna put her arms around my neck, which gave me easy access to her ample breasts. I fondled them on the outside of her sweater, then reached around her back and went inside her sweater to unhook her bra. With her tits free of the bra I started squeezing and pulling her nipples from under her sweater. Deanna was moaning and sucking hard on my tongue.

I broke the kiss and asked her if she liked her nipples sucked. She nodded yes, and I started to pull her sweater up over her head. Deanna was now topless and I was licking her tits and sucking on her nipples. Her nipples were hard and long. She whispered, “Suck harder.”

I alternated nipples. As I did, I progressively sucked harder. Deanna was panting and crushing my hand with her legs while I was rubbing her pussy through jeans. Deanna opened her pants and wiggled her jeans and panties down to her ankles. She was breathing hard and said, “Lefty, I can’t let you fuck me, but please finger me. I need to cum.”

I ran my hand from her calf to her thighs. Her legs were strong from all the dancing. When I got to her pussy, I played with her pubic hair. Deanna took my hand and put it on her wet pussy lips. I teased and tugged the lips. I played with her clit and Deanna was moaning into my mouth. I then plunged two fingers deep into her soaked cunt. Deanna was rocking on my hand. I inserted a third finger and began finger fucking her hard. Deanna was now sucking and biting my ear. While driving my three fingers deep into her pussy, my thumb was ramming into her clit. Deanna lost complete control and was pushing my hand deeper into her by pushing upward. Her orgasm was loud, wet, and intense.

Deanna pulled my hand away from her pussy and was rubbing my cock through my pants. She said, “You know, my husband and I started to date in high school and all through college. I have never felt or seen another hard dick.”

I opened my pants and my dick was sticking straight out. I had gone commando because I still hadn’t done my laundry. Deanna started stroking my dick while we continued to kiss.

Deanna whispered in my ear that she wanted to make me cum. It seemed she was intent on giving me a handjob. I said, “Deanna I want you to suck me off.”

With that I guided her head down and she proceeded to lick my dick. She kept her hand halfway up my shaft and only sucked the head of my dick. I moved her hand and pushed her head down so her nose was touching my pubes. I then used her hair to guide her up and down. I was soon ready to cum and when I moaned, Deanna tried to pull off of my dick. So, I pushed her head down, and held her on my dick, while I pulsed my cum into her mouth. Deanna was humming on my dick while I came.

When I let her up she told me she had never let her husband cum in her mouth. She said she was surprised how much semen I had and that it tasted better than she thought it would. After about ten minutes of cuddling, we decided we should head back to the bar. It would be late enough that no one would see me drop her off. When I dropped her off, I kissed her goodnight and whispered in her ear, “See you at ACME on Christmas break. Maybe we can find some mistletoe in the loading dock.”

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She laughed and said, “Or, maybe we can find a motel.”

I slept in on Saturday. I finally did my piled-up laundry. I went for a run. Time was dragging. Finally, it was 5 PM and time to head over to Donna’s. When I got there, Donna was dressed in sweats and bare feet with red painted toenails. She offered me a beer and I asked her about her Holiday. I heard about all the relatives, the minor spat she had with her ex when she dropped Lynda off with him, and that she would have to swim extra laps this week to burn off all the food that she ate.

I said, “I didn’t know you were a swimmer. You never told me that.”

She replied, “Well, I swam in high school. But, once I had Lynda, I was too busy. But, after our meet up Labor Day weekend ( see Donna’s Campus Visit for details) I realized that Lynda is at school late most days with cheerleading, so I have time to myself in the evening. So, I started swimming laps at the YWCA.”

We ate. We had a few drinks and settled in on the couch. We started to make out, and I could tell the swimming had definitely toned up Donna’s body. I whispered into her ear while nibbling on it, “The swimming has really made you more firm. Could I see you in your swimsuit?”

She smiled from ear to ear from the compliment and said, “Thank you for noticing! I will be right back.”

While Donna was gone, I stripped down to boxers. I figured if she was going to be in her swim attire, I should be in pseudo swim attire. When Donna came back, she was wearing a red one-piece bathing suit with shoulder straps, and which was tight against her chest and cut high at her crotch. It appeared to be a standard lifeguard bathing suit. I could tell that she likely trimmed her bushy pussy to accommodate this cut.

I told her she looked great in the suit. I motioned for her to turn around. She did. The suit was tight around her butt and most of her glutes were exposed.

“That swimming has given you a grade A ass!” I said.

I walked up behind her and put my arms around her waist pulling her butt into my stiff dick. Donna turned into me and we began making out. My hands were roaming her body, and she was moaning from the touches. I converted the back of her swimsuit into a defacto thong so that I had all of her fleshy ass in my hands. I picked her up and carried her to the couch. I sat her deep onto the couch and got onto my knees. I lifted her feet to my mouth and began licking and nibbling her toes. When Donna moaned, I started licking my way up her legs. When I got to her inner thighs, where the suit covered her pussy, I sucked a hickey on either side just below the suit line. Then I licked the wetness on her bathing suit made by her arroused pussy and worked my way up her body. When I got to her cleavage, I left yet two more hickeys above the suit line on each boob.

Donna was moaning with wanton desire as I kissed her deeply and worked the suit's straps off of her shoulders. We then peeled the suit off, and I began kissing my way south on her body. Stopping at her boobs, where I pushed them together, so that I could lick and suck both nipples at one time. Donna loved this as her nipples are extremely sensitive. I then alternated putting each breast completely into my mouth, which caused Donna to breathe more heavily. Finally, I slightly tugged each nipple with my teeth and Donna yelled, “Oh God, yes, that feels good.”

I worked my way down to her soaked pussy. I teased the labia and her clit, before I snake fucked her with my tongue. Donna grabbed my head, pushing my tongue deep while bucking into my nose.

Once her orgasm subsided, I took her by the hand and bent her over the arm of the couch. I then proceeded to fuck her hard from behind. “Yes, Lefty, Yes!” Donna wailed.

I kept stroking, and I grabbed each of Donna’s wrists and pulled her back slightly, arching her back. Donna was no longer calling my name; she was yelling to God. It was my turn cum. I shot streams of cum deep into her pussy and collapsed onto her back.

I whispered into her ear, “The swimming has made you more flexible. That was awesome.”

We got up and wandered to her bedroom. We lay down and snuggled and drifted off to sleep. At some point, I thought I was having an erotic dream. I awoke, and it was not a dream. Donna was under the covers sucking my dick and I was rock hard. I pulled the covers down and said, “Now that’s an alarm clock I need every morning.”

Donna looked up, smiled, and said, “I want you to lie there while I get my cardio in.”

She impaled herself on my cock and slowly leaned backward. Then she rocked forward. Her tits were swaying as she started to pogo stick on my dick. Donna picked up her pace. As she started to loudly orgasm, she leaned forward, and we were chest to chest. She stopped her riding and grinding. I started pounding her with pelvic lifts. My dick slipped out right as I was cumming and I shot my load between her ass cheeks, which eventually made us both a gooey mess.

We decided to take a shower. Donna was the first to go into the bathroom. Within minutes, I heard her scream, “Lefty, you asshole!”

I ran into the bathroom and saw Donna standing in front of a full-body mirror. She said, “I can’t believe you put those hickeys on my thighs and tits. I have swim class tomorrow and my suit will not cover them.”

I laughed and said, “I guess there will be rumors floating around at the pool.”

“You are such a boy,” she replied.

We showered. We had breakfast. We discussed tentative plans for my Christmas break. Donna left to pick up Lynda from her Dad, and I went home.

On Monday, I headed back to school. I decided on the way that I would stop at the high school basketball house party for about an hour. Many of the old JV players, from when I was on the varsity team, would be there, as well as many of my old teammates. As I was leaving the party and getting into my car, Lynda, Donna’s daughter, and two of her cheerleading friends came walking down the street. They stopped to chat for a bit. The two other girls walked to the house and Lynda said, “Hey, my Mom is at work, and then she has swim class. If you want we could go to my house. It’s not far. I really had fun last time and I have been thinking that I want you to be the first guy to fuck me.”

I replied, “Well, I would be honored! But I don’t have any condoms. Do you?”

Lynda shook her head and said, “We can get some.”

I laughed and said, “It’s at least a twenty-minute drive to a pharmacy. I really do need to get back to school at a decent time. I didn’t study this whole break. But, if you want, we can go to your place and still have some fun.”

Lynda climbed into my car and I let her give me directions to her house, despite the fact that my dick could drive to that house on auto pilot. When we got to the house, she took me straight back to her room. We sat on her bed and began making out. I whispered into her ear, “Do you remember what it was like when I licked you and then you sucked me?”

She said, “Yes, can we do that again?”

I said, “Yes, we will. But, we are going to 69 and do it to each other at the same time.”

Lynda kissed me and we roamed one another’s bodies some more. I stood up and backed away. I said, “Take your clothes off. I never saw you naked last time.”

She stood up and disrobed and said,” I have never been naked in front of a boy before.”

I replied, “You are beautiful, Lynda. How about turning around so I can check out your ass.”

I was thinking to myself that she is the spitting image of her Mom, just eighteen years younger. I had her turn to face me again. I then peeled off my clothes and approached her with my dick pointing the way.

She reached out to grab my cock while I started sucking her tits. I told Lynda to get on the middle of the bed on all fours. I then laid on my back and scooted under her until my face was directly below her pussy. I pulled her hips down putting her pussy onto my mouth. I began licking her sweet young cunt. She got the message as she started giving me head as well. I snaked my tongue in and out of her pussy and squeezed her ass hard using my thumbs to separate her cheeks wide. When Lynda started an orgasm, I rammed two fingers into her cunt. She was grinding back into me and loudly yelling, “Oh my God, oh my God!”

I started biting her ass cheeks, while she was cumming. Just playful little nips. But, then as I was cumming into her mouth, I bit a little harder. Lynda sucked me dry. She then turned around and licked her way up to my mouth and I could taste my cum on her tongue while we kissed.

I whispered into her ear, “I hope that I didn’t hurt you when I bit your ass. You had me out of control with your sucking.”

She replied, “It didn’t hurt. In fact, I really liked how hard you were squeezing my ass. The bites made me even more horny.”

We kissed some more and discussed Christmas break and that she wanted me to fuck her over the break. I told her we could arrange that, but now I needed to hit the road.

Lynda got up and went into the bathroom. As I was getting dressed, I heard Lynda yell, “Lefty, you asshole.”

I ran into the bathroom and said, “What’s wrong?”

She said, “Look at my ass! You left teeth marks. I have Phys Ed tomorrow, and we are required to shower afterwards in the big open shower! There will be ten girls in that shower with me. They are going to see this!”

I replied, “Oh, I guess there will be some locker room gossip going on tomorrow. Any chance the two friends you ditched at the party, who saw you leave with me, are in your PE class?”

She said, “Yes, and they will tell the whole cheerleading squad.”

I grinned ear to ear. We said our goodbyes, and I headed back to campus. All I could think about driving back was that this holiday weekend was better than any Penthouse Forum story I had read. How in the hell am I going to make Christmas break work!

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Written by Lefty63
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