Chapter 3

Ann and one of her pretty blonde friends arrived as my parents watched me open the gifts I received for my 16th birthday. I recognized the blonde as ‘Tina the Tongue’, from a couple of videos I had copied from Ann.

Thanks to a suggestion from Ann, my parents gave me a larger computer monitor and one of the highest capacity drives available; for video games, of course. Wink. Cough. Mom and Dad were on their way to Japan the moment we finished the cake and ice cream.

Ann told me, “I don’t have much money, but I think you’ll like what I’m giving you.” She played with the blonde’s hair and said, “She needs to leave in an hour. You two can do anything you want, if HIS UNDERWEAR STAY ON. Is that okay with you, Romeo?”

“YES! YES! PLEASE?”

“And is that okay with you, um ... Juliet?”

“Mmmm! That sounds nice!”

Ann smiled and put my hand in the girl’s. “Good. Go have fun.”

I led Tina, err... ‘Juliet’ to my room, and she kissed me and played with my chest as we stripped. Ann was super-sexy, but the blonde was a lot closer to my age, I thought around 20. I felt, tasted, and squeezed REAL BOOBS for the first time! I was playing with the body of a real porn star!

I got my first taste of vagina, and loved it. I licked, sucked, and fingered her pussy, and got her off after a lot of effort. I had no idea what I was doing, but it was a great fun. She let me hump her leg, and I came in my shorts twice.

I’d never gotten a better gift!

When the hour was up, Ann walked into my room. She saw me sliding a finger in and out of Tina’s pussy, as I tried to make her cum again.

“Time’s up. She needs a shower before she goes. Wash her back, then meet me by the pool, Romeo.”

Our soapy, sexy fun in the shower extended my time with the pretty blonde another half hour. She even let me play with her pussy some more, as she jerked me off and sprayed my cum on her feet.

She sat on the floor of the shower and did something even better. She licked my butt crack, then stuck her tongue in my ASS as she jerked me off again. I didn’t know it was possible to feel so great!

I thought about walking to the pool and meeting Ann nude, but decided against it, since she might get upset. I was happy about my decision when I saw my girlfriend, her daughter Emerald, was with her.

I walked near them and Ann said, “I’m glad you had a nice time with my friend. Since you have that taken care of, tonight Em and I will take care of your other big need.”

I was discombobulated. Did she mean more sex? Were the two of them going to have sex with me? Or give me blowjobs, maybe?

“You’re very lonely. Tonight you can sleep with us, in my bed.”

“But, um, isn’t Em too young?”

Ann laughed. “Naughty boy! That’s not what I meant! ‘Sleep’ as in ‘just sleep’. Lay in bed with us in our pajamas, and cuddle. It’ll be nice. Let’s swim a little, to burn off some energy first.”

That night I got my pajamas on, actually sweatpants and a t-shirt, and happily spooned between the two of them. As I started to drift off to sleep, I touched one of Ann’s breasts, and she gently guided my hand down to her belly.

I woke up feeling aroused, and noticed I had a firm erection. I opened my eyes and saw Ann had gone. 14-year-old Em had a hand on the front of my sweatpants. She was slowly stroking my penis through the thick fabric.

“Em, you shouldn’t do that.”

“Does it feel good?”

“AHHH! I could be in a lot of trouble.” I rolled out of bed and saw a look of disappointment on her face. “Sorry, but we can’t.”

After they left I had a mostly boring and unhappy year, until my next birthday.

After I opened my birthday presents on the day I turned 17, Mom and Dad headed to the airport again. Ann was going to be my ‘tutor’, since I didn’t need a nanny anymore.

When everybody else had left, I happily asked her, “So, Ann, when do you want school to start? What time in the morning? And how many hours a day?”

“I’m going to start teaching you right now, and I plan to keep teaching you until the day you get married, all the hours we’re awake.”

“What?”

“Since you’ll inherit a lot from your parents, you can pay experts to do what you need, accountants, lawyers, and so-on. Instead of writing and math, I’m going to teach you to make a woman’s body happy.”

“Uh...”

“Your parents agreed that I should be your tutor, and I can teach you whatever I want. A lot of our lessons will involve the two of us being naked in bed.”

I felt like I had a porcupine in my throat but was drowning in happiness at the same time. I managed to croak out, “Urrr...”

“If you’ll do what I say, I’ll teach you more than you ever wanted to know about love and sex.”

“Uh...” Again, I had no words. I blindly groped through the dark corners of my mind, but was unable to find the phrase, “Hell yes!”

Ann started by unbuttoning her blouse slowly. She took it off and put it over my head. I set it on the floor and watched as she did a sexy dance and took off her bra. She tossed it at me, and one of the bra straps hooked on my ear. My eyes nearly popped out, as I watched her shake her huge tits only a foot from my face. I loved seeing them bounce.

She stepped out of her underwear and said, “Open wide.” I tasted something tangy and wonderfully sexy, as the lacy black panties touched my tongue.

“Lesson one, women have three openings we use for sex, the mouth, the vagina, and the anus. I think you should practice with all three of mine.”

“Unnn...”

“Jake? Jake? Are you in there?” She snapped her fingers.

“Uh ... yeah. Such a huge surprise! I ... um...”

“When you’re ready, I’ll be in my bed.”

“Uh ... okay ... um...”

I stood there in shock for a few moments, trying to make it real in my mind. When I got to her bedroom she said, “Emerald and I don’t have any diseases, and we both have the birth control implant. You won’t need condoms with us.”

I stared at her beautiful nude body, unable to move. She reminded me, “It’s a lot harder to screw with your pants on.” She lit a cigarette as I stripped, then said, “Lay down on the bed. I think you’ll like this.”

She gave me my first blowjob, and it was a great smokey BJ. She took a big puff from the cigarette, then licked the head of my cock as she slowly exhaled. The wonderful action was hidden in a cloud of smoke briefly. She took another big puff, then wrapped her lips around the end of my dick and stroked the shaft, as she exhaled white streams through her nose.

I would never see a woman smoke in the same way again. I squirted into her mouth in half a minute, maybe less. Watching her swallow my spunk made it feel like she wanted me inside her, that she loved me.

“That was pretty quick. How many times a night can you cum?”

I was honest, and ashamed. “Six or eight, maybe more.”

She put the cigarette out.

“Let’s find out how many times it takes for you to give me an orgasm.” She laid on her back. “You’ve seen a lot of movies, so I’m sure you know what to do.”

I climbed on top of her, stuck my dick in her pussy, and jackhammered away. I squirted into her twice in only a couple of minutes.

She gently pushed me off. “That’s enough for now. Let’s talk a little.”

I wondered why she looked unhappy.

“Did I do something wrong?”

“It’s your first time, so I didn’t expect it to be perfect. You can’t just stick it in. A vagina is dry until the woman gets excited. You need to do some kissing and play with her body, to get her ready first. When you just shove it in dry, it’s very uncomfortable. Sometimes it hurts.”

“I’m sorry. I’d never mean to hurt you.” I felt awful.

“You’ll get better at it, but you have a lot to learn before I let you near my butt. Kiss me and play with my boobs.”

I was more than happy to French kiss her and attempt to breast feed.

“You need a lot of kissing practice too. Way too wet at the beginning, and you don’t just move your tongue in a circle. I felt like I was kissing a washing machine.”

“Sorry.”

“And nipples aren’t rubber balls. When you bite them or squeeze too hard, it hurts. They’re sensitive, like the end of your penis.”

“I’m sorry.”

“It’s ok, you’re learning. I’m wet now, so you can try my pussy again.”

I came in her vagina four more times, but didn’t bring her to orgasm.

There was a look of frustration on her face as she said, “I need to come at least once before we go to sleep. Try to get me off with your mouth and fingers.”

I didn’t like the taste of all the semen I had squirted into and onto her. It took me quite a while, but I finally brought her to a climax.

I started to get up. “Tonight was great! Thanks!”