The Tutoring; Spring Break

Another Evening with Anna

This is a fictional tale. All characters are 18 and older.

“The scent of pleasure and the sounds of slurping, sucking and sloshing filled the room as Anna bobbed my knob while sitting on my face in 69. I lapped at her swollen reddish-purple clit while reaming out her luscious ass with a glass dildo.

“That’s it, baby! You know just how I like it!” I bellowed into Anna’s creamy twat.

“Huh hu.” Anna mumbled with mouthful of cock.

A few moments later,

“OH FUCK YES!” I growled loudly as I felt my cock inflate!

I clamped my lips back onto Anna’s pleasure bean sucking hard! I buried the glass cock in her stink star as I began to erupt!

“Ugh!”

“Gulp”

“Ugh!”

“Gulp”

“Ugh!”

We traded as Anna devoured my man seed.

Left panting, I slipped the glass dong from Anna’s back door. Anna rolled off and lay next to me. I reached over, setting the lubed covered toy on the nightstand. After sweeping my tongue around my face to collect as much of Anna’s sweet juices from my growing beard,

“I am going to top off my scotch. Would you like a refill of your wine?”

“Yeah, sure.” Anna replied.

With glasses in hand, I went to kitchen.

As I returned to my bedroom with our refreshed drink,

“It’s Kelly. She wants to know if we can talk. Is that ok?”

“By all means, if you do not mind me staying this time.”

“No, but I have no idea what she wants to talk about.”

“Only one way to find out.” As I handed Ann her glass. She took a large swig, set the glass down and tapped the call button.

“Ri……..”

“Hey, it’s me.” Kelly whispered after immediately answering.

“Hey, sweety. Is everything ok?”

“Yeah, kinda. I’m just like upset with my best friend. Or at least I thought we were besties.

“Why don’t you tell me about it.”  

“Well you see…………” Kelly started. Sensing this could be a long story, I took a large pull off my scotch and set the glass down. Climbing back onto the bed, I settled my head between Anna’s legs as Kelly continued.

“Margie goes to Worten Finishing School and I go to Evergreen. Well, you knew that already, sorry. Before we left for school, we made a promise that as soon as one of us lost our virginity, we would call and tell the other.”

“Well, that sounds like a sweet promise made between friends.” Anna interjected.

“See, that’s the problem. I just found out she did like last year and never told me. And when I told her that Bri and I had not yet gone all the way, she kinda laughed at me.”

“Oh, sweety. I’m sorry. Why don’t you start at the beginning.”

“Ok. She’s home on break too. We went to another friend’s house for a small party with a bunch of kids we used to go to middle school with. At the party there was a guy she went with before going off to Warton They were never serious as we were just kids. He had a friend that came home on break with him. They wanted to go for a ride in my new car, so we left. Margie and Sam got in the back together, leaving what’s his name in front with me. As we drove, I could tell they were getting handsy. Before long, her head was in his lap. I mean the top was down and all! People could see and I told her. She didn’t care. Sam’s friend suggested we go park somewhere as he motioned to the bulge in his pants. I’m like eww, no, I have a boyfriend.”

“And then what?”

“Well, Margie finished Sam and then suggested we go back to her house. Her parents are away and her dad had restocked the wine cellar.”

“Not my place, but you’re not old enough to drink.”

“I know but it's ok. Her parents let us as long as we are not going anywhere.”

“Ok. Go on.”

“We open a bottle of pinot grigio and go to the game room to watch TV.” Kelly shared, reminding me of that senior year I went home with Reginald. Two guys, two girls a bottle of wine and a game of truth or dare made one incredible spring break.

“It wasn’t long before Margie and Sam were making out on the couch. His friend came and sat next to me on the other couch and tried to get with me. I told him again I was seeing someone. Before I knew it, Sam had Margie’s blouse open and her bra pushed up.”

“He wasn’t forcing himself, was he?” Anna interrupted.

“Oh no, she was very way it. Next thing I know, her skirt is up and her panties are off. Sam has his jeans down to his knees and is putting on a condom! He he he.” Kelly finished with a giggle.

“What’s so funny, sweety?”

“I’m sorry. I was thinking about how small it was. At least compared to Bri.” Kelly giggled again.

“Oh my. Um, that’s nice to know.” Anna awkwardly replied.

“That’s my boy.” I whispered into Anna’s pussy causing her to box my ears with her thighs and give me the shush sign.

“I mean, really! They’re going to do it right in front of me? Sam was humping away and I looked over at his friend and he’s holding a condom in his hand waiving it at me with a stupid smirk on his face.”

“What did you say to him?”

“I told him he wishes and just turn the TV up. Well. Sam finished in like thirty seconds then got up and went to the bathroom. This is where it gets weird and kinda gross. Sam’s friend gets off the couch, walks over to Margie, who’s still laying there half-dressed and her legs wide open. He drops his pants. Puts on his condom and starts doing it to Margie and she just lets him! Oh, and he’s not very big either. He, he, he.”

“Duly noted.” Anna replied

“Well, a minute later Sam was back and had his jeans off. He told his friend to roll Margie over onto her knees When she did, he knelt on the couch in front of her. She was now performing oral again on Sam while his friend was doing it to her from behind!” Kelly gasped in disbelief.

“I’m sorry you had to witness that sweety.” Anna consoled her young naive mentee.

“I know, right. I mean, do people really do this stuff? I know they like do this in porn, but those are actors.

Oh yes, sweety! Real people do engage in activities like that, I thought to myself. I wonder what Kelly’s reaction would be if she learned that her very own mother and the mother of her boyfriend had both participated in such debauchery. While their first three-way was with me, their first male female male threesome was with Reginald and myself.

“Sam’s friend finished in like a minute and left for the bathroom. Sam finished again and I thought it was over but nooooo! When the friend came back, he sat on the couch in front of Margie, and she began to do oral on him. After a few minutes, Sam put another condom on and started doing it to Margie again. Gross!”

“Are they gone now?” Anna inquired.

“Yeah. They got dressed and left a little while ago. After they left, I asked Margie if I really just watched her lose her virginity and she said no. I asked her about our promise, and she just laughed and said sorry. She said it happened after their winter social. She met a guy and snuck off to his car. That’s when she asked about when I lost mine. I told her that Bri and I were waiting for just the right time and that’s when Margie laughed again and said the first time was overrated and I should just do it and get it over with.”

“Well, if you ask me, I think you are Brian are doing the right thing in waiting until you are both ready. Your first time should be with a caring partner that respects you. The mood should be warm and relaxing. The place should be a comfortable and safe space. The backseat of a car is no such place for having intercourse. Well, at least not your first time. He, he, he.” Anna giggled as she gave me smirk and a wink as I continued to softly tease her still swollen pearl.

Anne had described her first time to a tee. I snuck her off campus to a hotel in town one Friday afternoon. After a meal brought up by room service, I presented her with a box with a new lingerie set. While Anna was freshening up and changing, I set the room. I lowered the lights and put a soft jazz CD into my portable player and perched the video recording strategically on the nightstand. After an hour of foreplay and exchanging oral, I had Anna climb on top. Letting her take control I caressed Anna’s thighs as she slowly lowered herself onto my waiting meat rocket. After a gentle first time and getting her first creampie, the gloves came off! I fucked Anna’s brains out over the course of two nights and until Sunday morning’s checkout. Every flat surface, every piece of furniture, in the shower and on the floor, I ravished this girl’s pussy. Oh, but it did not end there. On the drive back to campus, I took a small detour. Parking in the middle of an old pasture, she rode me in the backseat of that small two door car I had at the time.

“Is it right to be upset with her, Anna? I mean I don’t hate her for it, I just feel kinda hurt that she laughed at me.”

“Well, I understand how you feel. And yes, it’s fair to be upset with your friend as she did not respect your feelings."

"But why would she do that?"

"I'm afraid I have no answer. I can only say this. You two have gone off to different schools. You don't hang out as often now. She met new people and made new friends. Her new environment has reshaped her personality. You may not see it, but you are not the same girl that arrived on campus almost three years ago. The new people in your life and every new experience you have as also reshaped who you are. For the better I may add.

"Thank you, Anna. It's so nice to have some to talk about stuff like this."

"You're welcome, sweety. I hope I can help make some sense of it. Now, my advice is to not dwell on it and………………”

“Tell her to masturbate.” I whispered.

“NO!” Anna mouthed back on protest.

“Tell her it will make her feel better. Tell her that’s what you would do.” I whispered again.

“Ok, ok!” Anna whispered back.

“What I am trying to say, is that when I am feeling down about something, I give myself a little personal time. I think this will clear your mind and help you relax.”

“Like you mean I should masturbate? Like right now? And here?"

“Yes, sweety. I think it’s what your head……, I mean, your daddy would suggest for a moment like this.” Anna coached as a devilish grin crossed my face.

“It seems kinda weird to do that at a friend's house.” Kelly pushed back a little.

“I understand, but didn’t you say your friend had gone to bed and you’re alone?”

“Tell her you’ll masturbate along with her!” I whispered.

“NO!” Anna mouthed in resistance.

“Do as I ask, Miss Anna!” I prodded.

“Yes, Headmaster Richards.” Anna mouthed.

“If it makes you feel more comfortable, I’ll masturbate at the same time.”

“You would!” Kelly gushed.

“Yes, sweety. Anything for my Evergreen sister.”

After a moment of silence, there was some rustling. I envisioned. Kelly disrobing. It was again quiet. I rose to my knees and rolled Anna onto her right side. I then folded her left leg up and straddled her right. Settling into place, I slide my erect penis into Anna’s wet and inviting clam. Anne laid the phone to rest next to her head. With her hand now free, she dipped it under her bent knee and between her legs. Anna began to rub her clit as I slowly pushed in and pulled back. After several minutes, Kelly’s breathing was audible. Anna was in a groove as well. Wanting more,

“Ask her what she’s thinking.” I whispered.

“Tell me what you’re thinking about, baby.” Anna purred.

“I’m dreaming of my first time with him. I am wearing lingerie. The lights are off but the room is glowing with candlelight. There is soft music playing. There are red rose pedals on the bed. After giving each other oral, he asks me if I’m ready. I say yes. After I straddle him, I take his penis in my hand. It’s hard and throbbing. I press his tip to my wet labia. I feel it’s heat against my lips. I’m nervous but not scared. Taking a deep breath and letting it, I start to lower myself onto his penis. I feel my labia stretching open as he enters me. It goes in just a little then there’s pressure. It starts to burn a little. He asks if I want to stop. I say no and keep going. It feels like it can’t go any further but only the tip is inside me. Knowing it’s going to hurt, I bit my lower lip and spread my knees forcing my weight down onto his penis. I cry out in pain, but I did it. I’m resting on his hips now and every inch of him is finally inside me. I’m a woman now.”

“Yes, baby. That sounds so romantic.” Anna moaned as her orgasm was building.

“It only hurt for a moment and now I can feel him inside me. I feel full but it feels right. Like it was meant to be. He asks if I am ready to move up and down on his penis. I raise up until he’s almost out then slowly lower myself until our pubic hair is intertwined. Slow at first, then I get faster and faster. His big strong hands holding my bottom as she helps me to go up and down.” Kelly describes her fantasy.

Her breathing is now rapid and shallow. She’s getting close to her own orgasm as was I. With one hand on the back of Anna’s folded knee and the other groping her left breast, I pounded harder. My balls slapped Anna’s wet thigh with every thrust. The slurping sound of our soaked genitals was noticeably loud. If Kelly held her breath for a moment, I was certain she would her me. This could have only been topped by being on video call with Kelly. Pounding harder, all three of us were nearing a crest. A moment later, Kelly cries out,

“That’s it! Harder, harder! Don’t stop Daddy, I need to feel you cum inside me!”

“Yes daddy, yes! Please cum inside me!” Ann moans.

“Daddy’s cumming babies!” I growled.

“Ugh! Ugh! Ugh! Ugh!” I grunted as pumped Anna’s pussy full on my thick white load to the sounds of both my girls squealing with pleasure as their orgasm roll through.

I unmounted Anna, sat on the bed and laid back to catch my breath. Anna and Kelly were both panting. After a few minutes,

“Thank you, Anna. I feel much better now.”

“You’re quite welcome, sweety. I also felt a release. Now if you do not mind, I am going to go freshen myself up.”

“Ok, but before you hang up, can I talk to Daddy?” Kelly asked, catching Anna by complete surprise.

“Uh, uh uh, sh sure, baby.”

Anna rolled of the bed, cupped her hand to her leaking cunt and shuffled off the bathroom.

“Hey, baby. I’m glad you feel better now. I’m sorry that your friend said those things.

“Thank you for suggesting that. I did need a session of self-pleasure. I’m glad you were there.”

“And how did know this?” I pressed.

“He, he, he! I recognized your grunting.” Kelly confessed and continued, "Anna and were texting earlier today and she said her husband was still stuck out of town. I figured she might stay with you again.”

“Well, aren’t you quite the little detective.” I replied.

“I know, right! Well, I’ll say goodnight now. I need to go clean up as well. Tell Anna thanks again and that I said goodnight.”

“I will sweety. Goodnight my Kelly Cakes.”

“Night, daddy.”

I set Anna’s phone on the nightstand, tossed back the remainder of my drink and slid under the top sheet. Anna returned a moment later, finished her wine and joined me in bed. I turned off the lights. Anna quickly drifted off to sleep but I laid awake reminiscing about that spring break I spent with Reginald and his family.