The first 2 weeks back home were pretty busy. I met up with old friends, had about 8 nights out partying with my old crew and just had fun. I got a job as a life guard again and spent 4 days a week at the pool. My oldest firend, Erica, had also gotten a job at the pool. We spent a few late nights hanging around with each other at her place as her parents were up in Alaska for the summer. One of those nights though I think will interest everyone...

I guess I should describe Erica. She's about 5'5, lean and athletic like me (we were on the swim team together), nice ass and probably C cup breasts. Short blonde hair and blue eyes.

After work we threw on cover clothes then went to her place and cracked open a bottle of wine from her parent's stock. We sat around drinking away and talking about... honestly I don't remember. We were still in our life guard bathing suits and whatever we'd tossed on over them. It was still early, the sun was barely down, but for some reason I don't remember why, maybe the wine, we decided to do a joint. Erica rolled it and we had our hits from it. I've never been that into 420 but it was that kind of night. After that we decided to go use the pool in their back yard.

The pool was covered in an inflatable thing so it was private. We ran inside and zipped it up. Now Erica has never been shy either... "I don't wanna hafta dry my work suit, mind if I skinny dip Lilly?" Oh boy, yes I'd been around Erica naked before obviously showering and the like, but that was well before I'd 'changed' myself with Frank... But I couldn't exactly object, and decided just to go for broke... or maybe it was Mary Jane... but anyways I blurted out "I will if you will!"

"Deal!" and we stripped off naked.

We goofed around in the pool for awhile. In the end we just kind of sat on the lip and talked... and then the subject of sex came up.

"You started shaving Lilly, got a boy friend???" And she giggled as she looked at my hairless mound..

I looked down at my bare mound, then over at her, she was trimmed but had a landing strip... "Well... maybe... and I get waxed not shaved... I gotta find somewhere."

"Why maybe, you don't wanna tell me you got a guy pounding you? Come on we've been friends since like Grade 3!"

"I know I know... yea I got me a lover ok?"

"A lover... ohhh, not a boyfriend a lover... it is a he right? Older? Sugar Daddy???"

I felt a little uncomfortable "Yes I have had a guy fucking me, older, no he isn't a sugar daddy, just my lover"

"Mmhmm... why are you so embarrassed about it?"

"I dunno... this is just weird Eri..."

"Cause we're naked? We've been naked before? Or has something changed?"

I felt that feeling of surprise flush, I tried to hide it but it didn't work...

"Oh ho! You little minx! Ok spill the deets!!!"

"Erica listen... ok yea I've been getting fucked good..."

"But what, come on???"

My mind was working against me... the wine, the joint... "I've been experimenting..."

"ooh... like with another girl???"

I just nodded. "Yea..."

"And you like it don't you?"

"Eri..."

She held up her finger "Hey it's cool... was... well was it good? Did you ummm... go down on her?"

"Well... I... I don't know if i feel comfortable telling you this stuff..."

She moved closer to me... "Lilly, I'm curious... I've wanted to be with a girl?" And she suddenly kissed me.

Now my mind was screaming stop. I carefully pushed her back. I stood up out of the water and wrapped myself in a towel. "Erica no, I can't, I like you... I mean we're best friends I won't mess that up..."

Erica was obviously upset. She stood up, grabbed the other towel and practically ran to the house. I let her be a few minutes and got dressed, then brought her clothes and went in after her. I found her balling her eyes out on the sofa.

"Erica please don't cry... it's the wine getting to you..."

She looked at me "I... I'm sorry Lilly... now I feel stupid..."

"Why?"

She suddenly stopped crying... "Why? you mean you aren't offended?"

"Not offended, but I'm not comfortable with... well... us becoming more than friends."

She just nodded... "I think I need to sleep this off, I'll see you?"

"You betcha, text me tomorrow ok?"

Erica nodded, and I left. (Sorry if you wanted there to be sex but... no.)

The next day Erica and I went for coffee and laughed it off. The next month or so though our relationship felt a bit strained it finally went back to normal.

Frank finally messaged me halfway through July. I told him about the night with Erica, he responded that I'd done the right thing. He told me to finger myself but to resist coming for as long as I could every day. He also had me keep up using the Ben Wa balls as I had been. He said he'd set up a Skype session in a couple weeks.

Those 2 weeks were busy for me. On top of being a life guard I had some work for my dads medical office, redesigning their landscaping outdoors. Saturdays though were all mine, my parents were both at work. That Saturday rolled around. I didn't get dressed, just put on a bra and panties, and I waited by my laptop so excitedly that when the alert went off I nearly jumped out of my chair.

Frank came on the screen wearing... well... something in black leather?

"Hello Lilly... how's summer?"

"Ok, I'm missing our lessons"

"Good, well today you will get to watch" and he changed the view. There was a girl tied over the back of a chair. It wasn't Candace, I didn't recognize her, nor did I recognize the location. The room was dark, there was a post in the middle and some other furniture I couldn't make out. The girl had long black hair, very large breasts and brown areola. I couldn't see her face but her body was long and thin. "Lilly, this is Sam... she's pledged to my friend Walter... She's mine today because she needs discipline more than Walter can provide."

He walked around her. He ass was pointed way out. Frank showed me something. It looked like some kind of shredded umbrella?

"This is a crop... it's a handle with strips attached. You aren't ready for this yet Lilly, but Sam here" And he swatted her exposed ass with the crop "Is used to it. I thought you'd like to watch this Lilly?"

"Frank I..." I couldn't take my eyes off the screen. I was feeling VERY aroused "I do".

"Good, I'm going to strike Sam 18 more times before I turn her over... she can't count them as I have her gagged"

I watched him tease and use the crop on Sam. Her ass was turning red quickly. I couldn't help myself and slipped a finger into my panties and started to finger myself. Sam was screaming and... laughing? as Frank cropped her ass over and over. Finally he let her have a lot of strikes quickly then he put the crop down.

"Did you enjoy that Lilly?"

"Yes..."

"Are you fingering yourself?"

"Yes"

Frank just smirked at the camera then undid Sam from the chair. Now I could see her face. Small dark eyes... I'd say she had a elvish face. Frank took the gag out then pushed her to the floor on her knees and undid his.... umm... bottoms. Her hands were still bound but she moved into position as Frank pulled his cock out. She didn't need to be told, I watched her suck that cock I craved so much into her mouth. She sucked him hard, obviously with experience, for a good ten minutes. Frank just pulled his limp cock from her mouth. He hadn't let on that he'd cum but he obviously had.

He grabbed Sam by the hair and dragged her up. He pulled her back to the pole and tied her to the back of it standing. He bent down and I heard something being done, her legs were opened and she was mostly spread eagle. Her labia were clearly visible even on the iffy Skype connection, dark and totally bare. Frank picked up the crop again. He swatted her hard on each tit, then to my shock directly to her kitty. Sam screamed then seemed to moan in pleasure. Frank smacked her a few more times on each tit, then 4 times to her kitty hard.

I got myself to the edge and let myself cum. I couldn't stop myself... I think I cried out cause Frank looked over at the screen and smiled. He put the crop down then shoved a dong into Sam's vag. He worked it hard and she started laughing again... I didn't understand why she was laughing but didn't care really. I watched as she obviously came. Frank pinched her nipples as she came down causing her to shudder.

He came back over to the webcam "Did you enjoy that Lilly?"

"Yes I did..."

"Good, I'll be in touch" and he ended the session.

An email came the next Saturday from Frank with a list of 3 things to do:

The first was to pee standing up once everyday for the rest of the summer, and get used to doing it so I wouldn't have to concentrate so hard... I worked on that but it was still difficult.

The second was to use the Ben Wa balls every other day for 1 hour, 30 minutes standing. That one was harder to figure out to do without attracting attention, but I figured out how to do it early in the morning.

The third was to stop fingering myself period. I was not to touch myself until I saw him again in 4 weeks! This one was the hardest by far...

Summer rolled on slowly. I finished out my life guard job in mid August (there was a maximum number of hours per month for summer hires and I hit it for August only 2 weeks in). Erica and I didn't hang out as much. I did meet up with some other friends a few times, went to a couple end of summer parties, and the like. It was over so soon, but one last thing to tell you all about...

At one party, out in the country, I met this girl named Emony. She was a tall lean black girl and we hit it off. Probably 6' tall, big round tits DD, maybe DDD, size and a tight firm body all the way down. She was a marathon runner. We went off from the party somehow ended up alone in a kind of grassy clearing. We were both a bit sloshed.

We started getting really close and somehow we kissed. I didn't pull back and neither did she. I was only wearing a bikini top and she only a t-shirt. I don't remember all the details but I ended up on my back topless with her on top of me sucking on my nipple. Her skin was soft and her hair smelled nice and sweet. She pulled her shirt off and her bra. She rubbed her tits against mine and we kissed again. Unfortunately someone else was coming and we grabbed our tops and went and hid as 2 guys walked around and dragged on joints. We giggled, put our tops on again and that was it. (Again, sorry there isn't more to tell... but I have to be honest about what happened). I did see Emony again a year later but we never got intimate again.

Late August I heard from Amy, she'd found a place as was taking it if I moved in with her or not! I talked my mom into taking me back a couple days early. The apartment was really nice. Basement, about 15 minutes walk from campus, private entrance, parking, 2 bathrooms and bedrooms, laundry and a full kitchen. I agreed to move in and got my deposit back from the dorm reservation.

So the summer break was over. My new semester started that Tuesday, right after the long weekend. But I had 5 more days to wait till my other education continued...

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The Sex Student - Part 15 | 2016