I turned 18 in February, and I made it my goal to find a girlfriend or at least have sex. By the summer I still didn't have a girlfriend neither had I done the deed yet. But I swear I never thought my first time would be with the divorced MILF next door whose son was a Junior in college and lived in the dorm. It all started innocently enough when Janet (Ms. Davis) saw my mom and I pull up in our driveway and after she and my mom talked for a few minutes Janet asked if I could help take some things inside for her that were a bit heavy.

Mom volunteered me for the job, so I had no choice. I'm no Mr. Universe, but the stuff Janet wanted me to carry was stuff my mom easily handled every week. Like dog food and mulch. But after I looked at Janet, it was obvious she wasn't wearing a bra and her big boobs swayed back and forth, and her hard nipples were practically poking through her T-shirt, so I really didn't mind. Now I had no idea where this would eventually lead, I figured I'd get some spank material for later. The trick was to look as much as you can but to not get caught. Especially with my mother still there. Mom either didn't notice or didn't care about braless Janet. That's when I noticed mom's nipples were hard too. Either she wasn't wearing a bra also or she had gotten hard in a secret bonding with another female. Obviously, I've never seen my mom's boobs. but I could tell they were much smaller than Janet's boobs. I also almost came right then and there when they hugged, and their hard nipples touched.

After unloading the items from her car. Janet asked if I could spread the mulch and play with and walk the dog, a Great Pyrenees named Cash. Her son usually did this, but he was away at college even during the summer as he had a job near the school. She explained.

I had to remember to look into her eyes as she spoke and not just stare at her incredible tits. Janet had long black hair, brown eyes and a plain face with freckles. She also had freckles on her chest wear her shirt didn't cover and I wondered how far down they went onto her tits. I always had a thing for freckled covered boobs from the porn I watched.

After about 2 hours of doing things for her, she called my mom and asked if I could stay and watch a movie as sort of a payment. She'd feed me too so my mom wouldn't have to cook. Mom wanted to go meet her friends and see a movie herself, so it all worked out.

About an hour into the movie I looked over and noticed Janet was sleeping. I also noticed her shirt had ridden up, exposing the bottom of her breasts. I said her name a few times, but she was totally out. I knew it was wrong, but I just had to look at those tits. My logic was she should have worn a bra or at least put one on when I came over. She did neither, so in my mind she wanted me to see them, or she was a big tease. Either way I was going to look. To test the water, I poked her arm. Then pinched it. No reaction. Then, before I could stop myself I lifter her shirt and exposed her huge tits. They were long and tubelike and spectacular. And yes, the freckles did go to her tits. Her milky white tits looked great in the glow of the TV. Her areolas were big and had bumps on them and her nipples were on the long side, but not too long just the perfect length. I considered taking a pic but thought that was going too far. Plus, my luck my mom would look in my phone and see it.

I pulled her shirt back down. "Ms. Davis!" I said loudly and shook her awake.

Her eyes popped open, and she sat up. That's when she noticed her shirt was pulled up a bit, revealing her stomach. She quickly looked at me and then back down to make sure her boobs were covered.

"I should get going. My mom will worry if I'm not home soon," I said.

"Right," she said. "Thanks again for the help."

"Anytime," I said.

"I was hoping you'd say that. Could you mow the lawn tomorrow?"

"Sure, what time?"

"Anytime is good. I'll even pay you," she offered.

"Deal," I said.

Then I went home and jacked off to the mental picture of those tits.

"Hello, Ms. Davis," I said when she answered the door.

"Hey Nate. And please call me Janet." A picture of me screaming her name over and over as I fucked her missionary as her boobs bounced all over the place popped into my mind.

"Right, Janet," I said, snapping out of my sick and twisted thoughts. Although she was wearing a white T-shirt sans bra and not only could I see her nipples (which were hard again) but her areolas were prevalent too.

Of course she wanted it bagged, so it took me three hours. I was a sweating mess. Then I had to walk Cash again. He was a cool dog and people kept stopping me to ask about him.

After a nice drink of water, she handed me Fifty dollars. "Here's your payment," Janet said. "And as for the tip. Did you like what you saw yesterday?' she asked.

"What do you mean?" I asked looking quickly away.

"Don't even try and deny it. I saw you looking at me even with your mom right there. I also felt you lift my shirt up to look at my boobs. So, did you like what you saw?"

Fuck it, might as well admit the truth. "They're awesome!" I said.

She laughed and then said, "Thank you. I grew them myself," she joked.

Stunned, I looked at her confused.

"It's a joke," she said.

"Oh, right," I said and laughed nervously.

"Would you like to see them again?" she asked.

"Obviously," I said.

"You can look but you can't tough," she said. Then before I could reply she took both hands and lifter her shirt and flashed me her huge tits.

I bent down and got as close as I could since I couldn't tough them.

Just then the doorbell rang, and we both jumped. Her tits bounced up and down and I almost came in my pants. Worse than just an interruption, it was Carol, my mom. Then the door opened, and Janet barely put her shirt back down when my mom walked in, asking "Hello, Janet. Have you seen Nate?"

"Yes, he's here. Didn't he tell you? I asked him to come mow the lawn for me today," Janet explained.

"No. It must have slipped his mind," Carol said.

"Yes, well you know 18-year-old boys. All they think about is sex. Everything else goes right out the window," Janet said, smiling.

"Oh yes. I know. Is that what you're thinking about now Nate?" Mom asked.

"Mom!" I said, turning even redder than I was at almost being caught looking at our neighbor's tits.

Both women laughed at my discomfort.

"Well, we better go. This one still has his own chores to do," Mom said.

"Thanks again, Nate. I really appreciate you looking after me," Janet said with a wink. Then gave me a hug. Her tits squishing into my chest. Then she whispered, "Come over tomorrow and I'll let you touch them."

I practically ran out the door before either one could see my hard cock through my jeans.

The next day I told my mom I was going back to Janet's house to help her again. She said I had to call her Ms. Davis even if she told me to call her Janet. Whatever.

When I got there Janet was wearing a shirt and a bra, I could see the straps. She saw my face and said, "Don't worry I'll let you tough them, but you need some guidance in seduction first. You don't just go right to the boobs or grabbing the ass. A woman likes to be seduced as well as she likes to be fucked, but if you seduce her first, she'll let you fuck her anytime you want."

Janet taught me how to kiss. I actually got hard when our tongues touched. Then she taught me how to take off a bra. Several of them as they're not all the same. Watching her tits spill from her bras almost made me come over and over.

Finally, she let me touch her boobs. I grabbed, cupped and squeezed them. I got behind her and grabbed them, pinching the nipples. Then I spun her around and bent down and took them in my mouth. First one then the other. I licked all over them, even lifting them up and licking underneath. (She later told me no one had ever done that, and she liked it.) I traced her areolas with my tongue licking the bumps with my tongue while tracing her other areola bumps with my finger.

After about 30 minutes, she told me to stop.

"My turn now. Take off your pants," she instructed.

"Um..."I said.

"You're not the only one who's going to have fun today," she said. "Tit for tat, so to speak."

Janet traced my hard cock through my boxer/briefs, tickling the head and my balls and laughing when I jerked away. Then she yanked down my underwear and out sprang my cock. I guess it was bigger than she expected because she gasped.

"Oh, you have nothing to worry about, Nate. Nothing at all."

Then Janet grabbed my cock and started stroking it. I reached up and played with her tits and it didn't take long before I was ready.

"I'm going to come," I said. She aimed my cock at those huge tits, and I let lose all over them. She rubbed the head of my cock on her nipples, leaving traces of sperm on them. Then I watched as she licked the cum from her tits with her long, thin tongue.

The next day she taught me how to eat pussy. She was shaved but had a landing strip above her cunt. Her fat pussy lips were great to lick and suck on. She didn't taste as bad as I thought she might and there was no fishy smell either. She told me not to be shy and to try things. Most women liked guys that just did stuff, if she doesn't like it, she'll tell you.

After making her come twice she gave me a blowjob. When she looked up at me after having sucked my balls while stroking my cock our eyes locked. Then I felt her tongue swirl around the head of my cock, and I warned her I was going to shoot. She clamped down and I unloaded in her throat. Janet swallowed every drop. I ate her out again and ran my fingers through her landing strip while using my thumb to rub her clit. I had her coming in no time.

The following day we graduated to fucking. I wasn't sure how tight she'd be as I fingered her with two fingers while eating her out, but her cunt clamped onto my cock like a vice. She was really wet too and in no time we both came. My seed spilled out of her after a while. Without a second's hesitation she turned over and told me to fuck her from behind. I did. We both lasted longer, and she came, squeezing my cock until I erupted inside her. Her pussy was like a velvet glove over my cock. I told her this and she told me not to expect a tight or wet pussy from every woman. We're all different she told me.

Mom was gone the next day, so I left a note explaining where I was, but not what or should I say who I was doing.

I was fucking Janet from behind when she told me to spank her.

"What?" I asked.

"Spank me. I've been a bad girl," she said.

I did as instructed, and she told me to spank her harder. I did.

Between Janet yelling at me to spank her and me grunting and spanking her neither one of us heard my mother walk into the bedroom.

"Oh my God! Stop spanking the neighbor!" Mom said. Then added, "Wait, stop fucking our neighbor! Seriously. What the fuck?" Mom asked looking between Janet and myself.

"Fuck Carol, don't you ever knock?" Janet asked.

"I did. Obviously, you were too busy fucking my son to answer the door."

"Look, he wanted to learn, and I was willing to teach him. Plus, he is 18. Would you rather he didn't know how to please a woman?" Janet asked.

"I'd rather not think about my son pleasing anyone, let alone the next-door MILF." Mom said.

"So, you think I'm a MILF?" Janet asked coyly.

"Don't get cute," Mom said. "No wonder he was always coming over here. You never wear a bra, and your nipples are always hard."

"Well, flaunt 'em if you got 'em," Janet said, lifting her tits.

"Hey, I've got nice tits too," Mom said, taking off her shirt, she too wasn't wearing a bra. Her pair shaped tits also had freckles but were smaller and her areolas were medium. Unlike Jante's nipples which hung low, mom's pebble-like nipples tilted upwards. I can't believe I'm staring at my own mother's tits.

"Nathanial!" Mom shouted. "I'm your mother!" Then she noticed my hard cock.

"The one who deserves a spanking is you!" she said and grabbed me and pulled me across her legs and started spanking me. Hard. After about ten smacks she told me to stand up. My cock was even harder.

"Pervert!" Mom said, shaking her head. Then she noticed the precum my cock leaked out on her sweats, and she peeled them off. She wasn't wearing any panties. She was shaved with no hair at all, but she did have a bellybutton ring. She had sandy blonde hair, hazel eyes and a cute face.

Suddenly, she grabbed Janets hand and pulled her across her lap and said, "You like getting spanked? We'll see how much you like it after I'm done."

Janet's tits swung like two pendulums, while moms bounced every time she made contact with Janet's ass. When mom shoved a finger in Janet's pussy I decided to join in too and shoved my cock in mom's mouth. She opened right up and before I knew it, she was sucking my cock like a pro or what I assumed a pro would suck a cock like.

Janet soon came and I felt mom's tongue run over and over the head of my cock, then she looked up at me and that's when I lost it. I blasted my load inside mom's mouth, and she too swallowed all of it, save what she traded with Janet when they kissed.

Janet then made me show my mother what she taught me. The weird part wasn't fucking my mother it was kissing her. Her fat tongue was different than Janet's, but I liked it too after I got used to it. I licked mom to two orgasms, then I fucked her.

The Janet and Carol (mom told me to call her Carol as saying mom freaked her out) rimmed me. I shot a load inside Janet's mouth while mom I mean Carol licked my asshole. I then had to rim them.

I asked if I could jack off on their tits. They both agreed, even rubbing their nipples together. In no time I shot my last load.

The next day Janet came to our house, and I fucked her and mom in the ass. I impressed them both so much they introduced me to their friends for hookups. Sometimes together, sometimes one on one. I did find a girl my own age to date, but I'll always be grateful to Janet for showing me the ropes. She still has the best tits I've ever seen, just don't tell my mom.