Not only were my parents divorced, my dad who had custody of me had just remarried. Alyssa was in her mid 20’s but acted like she was 18. My dad met her one night at a club in Hoboken while celebrating a friends bachelor party. No she wasn’t a stripper, she was just at the bar with some friends.
At first glance Alyssa was the most perfect girl this 14 year old boy had ever seen. Guess dad thought the same thing. She was no more than 5 foot 3, she had deep brown eyes, straight black hair that ran a little down her back. She had pouty full lips and a stereotypical ethnic nose. Dad said the nose was trait passed down to women of her religion. He convinced me it made her more attractive. Not to mention her sharp voice and general aggressive attitude demanded attention.
Dad worked on wall street and we were pretty well off. After the wedding I think dad spent more time working to pay off what Alyssa was spending. Alyssa didn’t just buy for herself, she was always buying stupid expensive gifts for me, dad , the pool boy, the gardener. the neighbors, the dog.
I had just turned 14 as the school year ended. I wasn’t a dumb kid or a nerd. I wasn’t in bad shape but I wasn’t a jock. I knew nothing about women and even less about girls my age.
From the start my new step mother wanted me to treat her like my new mom. Under some circumstances it might have been easy. Unfortunately for all of us, it took my step mother a while to realize that it was easier for her than it would ever be for me.
Alyssa was always wearing revealing clothes or skimpy bikinis. A couple times I got a quick look at her tanning topless out by our pool. I made a point not to take more than a quick peak out of respect for her and my dad. The problem was this girl (my step mom) had an incredible body.
After a while it seemed to me that she didn’t even think her nudity would pose me a problem. She was too wrapped up in the “mother” idea.
Lucky for me she almost always had a friend with her that would distract me from the truly embarrassing.
My dad and I had always spent a week or two of each summer in the Hamptons. This year Alyssa made sure our weekly house was ours for the summer. I figured it cost a lot, because my father had to work most weekends to pay for it. In fact I don’t think he came over after that first weekend.
No joke, 5 minutes after dad left that first Sunday night around 10pm, 5 of Alyssa’s girl friends were knocking at the door. Alyssa got dressed up, gave me money to order pizza and went bar hopping with her friends. It was nice that she thought I was old enough to watch my self.
After pizza and a few (after dark) movies I decided to go to sleep. Every summer I had taken the small bedroom in the back of the house as mine. There was a twin size bed that just about filled the room, it was right across from one of the bathrooms and near the back door.
I never thought of my self as a sound sleeper, but I sure didn’t hear the women come home. I awoke when I felt my bed shake. I opened my eyes just enough to see two of Alyssa’s friends sitting on the edge of my bed.
I didn’t know what they were doing but I heard a weird bubbling sound and also heard the girls cough a lot. I could hear the others drunken noises coming from around the house.
With only a shimmer of moonlight coming into the room I thought I saw one of the girls undressing. I never did see her put anything back on. The taller of the two girls grabbed her friend and pulled her close.
“Its time we stop fooling ourselves. I want you.” As they drew close to a kiss they both broke out in laughter. One girl pushed the other onto the bed and on top of me.
She didn’t notice me. The girl on the bed crawled under the sheets, right next to me and passed out. The other just passed out naked (I assume) and sprawled across the bed. God I hoped I didn’t have to piss that night.
I had all kinds of erotic dreams that night, and when morning came I woke up alone in my bed. The sheet and blanket were gone, I just lay there on my back trying to wake up.
I had decided last year to stop wearing pajamas now that I was older. I slept in an old Metallica t shirt and pair of grey sweat shorts. When I cleared the cobwebs out of my heard I heard the shower running in the bathroom across the hall
I could smell eggs being cooked and heard my step mom and some of her girl friends in the kitchen talking.
I was about out of bed when I noticed that I had woken up with a full blown morning erection. Erections in general were still new to me but I knew it would be obvious to anyone who saw me.
In half a panic I reached my hand into my a shorts to move it and hopefully hide it.
At the same exact time my hand gripped my erection, the bathroom door opened. The taller girl from the night before walked out wearing only a towel. She left the bathroom door open long enough and wide enough for me to see another one of Alyssa’s friends naked in the shower trying to shave her legs.
I couldn’t help but stare. I was seeing my first naked girl in person. The naked girl in the shower looked up and saw me watching her, she didn’t scream or yell. The naked girl in the shower winked at me right as my step mom came walking in my room.
Alyssa gasped in disgust. She had caught me with my hand down my pants, my hand on my erection, and my eyes staring at her naked friend.
“You little pervert.” I think they both said it. The girl in the shower charged out of the shower and was now trying in vain to hold a small towel in front of her.
“What do you think your doing you little pervert?” Alyssa demanded to know.
“Yeah what? You little pervert?” Yelled the girl who had been in the shower. Her towel hid nothing, and my erection was growing harder.
When it all hit me I quickly pulled my hand out of my shorts.
“Dina. Your not helping!” My step mother told her half naked friend. “Go get some clothes on and let me punish my step son!”
I was pretty sure that Dina was either still drunk or very hung over. Using the towel to cover her front side she turned and walked back to the bathroom making no effort to cover her naked butt.
“I am talking to you Tommy” I didn’t hear my step mother clearly till the bath room door shut,
That was when I realized how it must have looked. I tried to defend myself. “No, Alyssa its not what it seems” How do I explain this?
“What ever it is, I don’t like it. I can’t let you grow up to be a pervert. You need to learn to respect women of all ages. You need a spanking young man.” Alyssa pulled me off the bed and to my feet.
I tried to pull the bottom of my t-shirt down past my shorts to hide my erection. Then it hit me. `Did she say spanking?’ I thought to myself.
Spanking was new to the family, dad had never spanked me but my new step mother had made it clear to me that it was an option. I thought it was an idle threat. I mean I was to old to be spanked.
Alyssa marched me into the living room and I followed without a struggle.
Two of Alyssa’s friends were still here and in the living room watching TV. The first girl with the towel was now dressed .
“Dina, come out here pleas!.” Alyssa yelled.
The two hung over girls turned their heads to see why Alyssa was yelling.
“Give me that t shirt” my step mother demanded, as she was pulling it off me. She pulled me around the couch and in front of the television.
Neither girl watching tv seemed to mind. A minute later Dina came down the hallway wearing only a pair of red panties. I was seeing my first pair of naked female breasts.
I was seeing my first pair of naked female breasts.
I was seeing my first pair of naked female breasts.
All of a sudden my heart was racing and all my blood was going to one spot. I was pretty sure I was going to have an orgasm and I was pretty sure I had no say in the when.
“Dina.” Alyssa scolded her friend. “Your evil. Girl. Tommy is supposed to be punished, not rewarded.”
“Punished?” I asked at the same time as one of the girls on the couch.
“Yes. My perverted step son” Alyssa announced to the room. “Was peeping in on Dina in the shower.”
The girls just shook their heads.
“That’s not the worst of it. He was playing with him self too.”
“No I wasn’t” I tried to protest but the bulge in my shorts said different.
“You like spying on my naked friends, I think they deserve to watch you get punished. They deserve to watch you get spanked.”
“Alyssa. You can’t” I couldn’t even beg right, the whole idea hit me with a big shock.
I was pretty sure nothing could be worse than being spanked by my new stepmother in front of her hot friends.I was wrong. “NO!” I screamed out in terror as I felt Alyssa’s hand grabbing the elastic from my shorts.
“Yes you little pervert.” In an instant my young step mother easily pulled my sweat shorts to my feet.
All the girls cheered, laughed and awed at my erection(like the 4th of July). With the strength of a mad step mother Alyssa pulled me over her lap and began a bare handed spanking of my naked behind. She wasn’t that strong, and it didn’t really hurt.
The embarrassment and humiliation of being spanked naked by my young step mother in front of her young half naked friends was pain enough. No girl had ever seen me naked before. Now three of them had seen my erection and were now watching my naked butt get spanked.
After about 20 spanks Alyssa seemed content. She motioned me off her lap and helped me stand up. First I was facing her and my erection was almost in her face. It was all I could do to hold it back.
“Now apologize to Dina, and promise me you won’t ever spy on my friends in the shower again.” My step mother ordered.
I slowly walked around the couch towards Dina, my erection swinging back and forth. Her perfect naked breasts had me mesmerized. “Dina, I am very sorry. I didn’t mean to spy on you and I won’t do it again.” I said as sincerely as I could.
“Aww its ok sweetie, your to cute and naked to be mad at.” She grabbed me and gave me a huge hug. My face buried in her perfect naked tits was ecstasy. At the same time Dina was sliding my hand down her back towards the band of her panties, she was also lifting her leg to brush against my erection. I couldn’t believe it.
Looking around Alyssa seemed preoccupied for a second, but the two girls on the couch were watching me closely. Dina slid my hand under the elastic of her panties and flush against her bare butt.
Her soft skin felt like heaven in my hands. I started breathing very heavy. “Oh No” I gasped when I realized I couldn’t hold it any more.
“Go ahead sweetie don’t fight it” Dina told me, after she stopped “hugging” me and stepped back. The tone in her voice was ecstasy to my ears.
“No!” Alyssa yelled. “Do fight it. I am not cleaning that up.”
“I can’t” I was almost crying. I tried as hard as I could to hold it back.
“You will make a mess of the living room.” Alyssa ran over to me and ushered me towards the big glass door that led from the living room to the side deck. She swung open the door and pushed me out side.
I fell on my knees onto the wooden planks of the elevated deck and let the orgasm flow. I know I was moaning and breathing heavy. Alyssa’s three friends clapped and cheered from inside.
It was the greatest experience I had ever had. I never knew such joy could exist. I didn’t care the older women, or my step mother for that matter were watching. I think that made it better.
I gathered my self hoping to stand up and walk back inside and to the shower. With a deep breath and a smile on my face I tried in vain to stand up. My knees were still weak and my head was still dizzy. I shook my head to clear my eyes.
A small hand reached out to help me up. With out thinking I took the hand in mine and let my self be helped to my feet.
With the tiny hand still resting in mine I tried to blink the sunlight out of my eyes and see clear. As my eyes focused I saw standing in front of me a pretty young blonde girl.
The young girl was around my age. She was very petite and wore a small white bikini top and jean shorts.
Her blue eyes and blonde hair caught my attention. My eyes moved up from her belly button past the tiny cleavage in her bikini top. She was staring right at my former erection and forced her self to move her eyes up to meet mine.
“What a neighborly welcome!” She was grinning from ear to ear. “I am Beth, I live over there.” She pointed a few houses down.. “Wow, that was. I didn’t know that.. I mean.. You’re the first boy.. I ” She was speechless which I found out later was some feat.
For a long moment with stared at each other in silence, her soft tiny hand still holding onto mine.
“Um do you know your naked?” she finally asked.
“Huh. Oh ” I was the one now speechless. The situation and what this pretty young girl had witnessed me do was starting to hit me. I am sure my face was turning bright red.
Every thought of panic ran through my head.
Thank god for Alyssa.
“Tommy!” Alyssa grabbed me and pulled me inside. “Go take a shower.. NOW!” She ordered with one final swat on my naked butt.
“Tommy.?” I heard Beth call me. Without thinking(something I wouldn’t do a lot) I turned around showing her a full view of my nudity.
Her smile was bigger than ever. “Nice meeting you!” Was all she had left to say.
I ran off towards my bathroom past the other women who just applauded and whistled.
“Beth right?” Alyssa asked the young girl. “Who are you?”
“I live a few houses over, with my mom, sisters and little brother.” Beth proclaimed. “My mom sent me over to welcome you to the beach”
“Well tell your mom I said thank you and I look forward to meeting her”
“Actually she wanted me to invite you and “Your son?” to lunch tomorrow up at our house”
“That would be great. Yes he is my son and we will be sure to be there.” Alyssa answered with a weird tone in her voice.
“Will Tommy be wearing clothes tomorrow?” Beth asked. “He is defiantly the oldest boy I have seen naked. Sure is different than when I give my brother a bath.” Beth had an excitement in her voice with everything she said. “What was that stuff?”
I was still listening from the bathroom, when my step mother interrupted the young girl and shocked me.
“Sorry dear, he will have clothes on tomorrow.. If your lucky, maybe I can get you a private show” Alyssa finished with a laugh.
(Was she serious) I thought?
“Really..? Cool. Thanks.” With that Beth ran down the steps and was gone. I took a shower wondering what this lunch could possibly be like.
The rest of the day went by without anything weird happening. Dina joined us at the beach for a little while then left. Alyssa and I returned from the beach in the late after noon.
Our beach house was just across a small street from the beach. It was built on the slope of a small hill and had large stilts supporting it. Under the house was where Alyssa parked her car. There was an outdoor shower and a close line near the steps that lead up to the back door near my bedroom.
On the other side near the street was a set of steps that led up to the larger deck when I had met Beth.
Alyssa told me to shower in the outdoor shower, hang my suit on the line, then head up stairs and get ready for dinner.
The shower was covered, but just barely. The small wood fence had gaps in it from wear and tear and the door barely closed and didn’t lock. If anyone was near by and looked hard enough they might see something.
After my shower I wrapped myself in a towel and hung my suit on the line. I noticed that Alyssa’s bikini was already hanging on the clothesline. When did she do that?
When I got up stairs Alyssa was still in the indoor shower. I went into my room and got dressed and then went and watched TV in the living room.