I had to pinch myself.
Twenty-four hours before I was standing in Chicago snow and brutal winds that nearly knocked me off my feet, and now my barefoot toes were in ankle-deep surf on a tropical island. As the song goes, “What a difference a day makes.”
Adding to my elation, I was accompanied by two beautiful women. Admittedly, they were relations: my stepsister and my stepmother, but regardless, they made me proud as we walked the surf line under the admiring stares of sunbathers. Both my nineteen-year-old sis and my thirty-nine-year-old stepmother were the obvious objects of those stares. I was of secondary interest, although my six-foot, rock-solid eighteen-year-old physique was a worthy accompaniment to the family. Additionally, I was blessed with a thick cock that bulged provocatively in my speedos. Even from a distance, I could see sunbathers staring at us.
Our getaway from northern climes was a reward of sorts. My dad had died after a long, drawn-out illness a month or so prior, and at my stepmother’s suggestion, we were finalizing our grief in his honor with a vacation to the tropics. He had revealed in his final days that he had a fund designed exclusively for that purpose.
“Look, we all realize my days are numbered, and I’m ready for whatever is next. I know this is a sad time for you, and so I have something to tell you. You need some sunshine in your life, and I’ve made all the preparations once this ordeal is over. And I’ll be there in spirit. I promise.”
So after the funeral and the appropriate end-of-life celebrations and grieving, we were washing away our sorrow in the warm waters of the Caribbean. Our trip coincided with my eighteenth birthday as well. For me, it was truly a way to forget the ordeal we had just been through. But more about that later.
Our family had always been tight-knit as well as a bit unconventional. My bio-mother left my dad when I was a toddler, and my dad remarried soon after to Jeanette, my stepmom who had a daughter who was four at the time. My sister and I became very close from the start. Since she was older, she tended to protect me and as we grew up, our bond only increased.
My dad had been raised liberally by his hippy parents, and our family had similar values. Our family life was an open book. My parents entertained often, and we had lots of “uncles” and “aunts,” as we called their close friends. We later learned that our parents were involved in “swinging,” although that didn’t come out until we were nearly out of high school. We knew our parents had liberal views about sex, but we didn’t understand the extent of it until my sister discovered a video of one of their parties when she was eighteen.
“Oh, my god, Sammy! You have to see this!”
We watched in awe as “mom and dad” had sex with several “uncles and aunts.” Eventually, Mom realized our discovery and did her best to explain what we had seen. And after her explanation, things that we had wondered about started to make sense. Neither one of us harbored ill feelings toward our parents. We accepted their behavior after a serious family discussion where it was stressed that we were old enough to make our own informed decisions about sex.
My sister and I experimented with each other to a degree in our later teen years—nothing serious–just kissing and a little touching. I was a bit timid around girls, but Julie had several boyfriends during her last two years in high school. And with good reason: she was a knockout.
So when I asked her embarrassing questions about the things not covered in school, she took me under her wing. When I was sixteen, she gave me lessons in kissing and what turned girls on. She let me feel those solid orbs, and even on one occasion, she showed them to me. When I showed her my penis as payment, she couldn’t resist and asked me if I wanted a hand job.
“Oh my god, Julie. Sure. Would you do that for me?”
Her response was to try to wrap her hand around me.
“Jesus, Sammy. Your cock is huge. It’s way bigger than my boyfriend’s, and I thought his was big.”
Her compliment caused me to swell with pride, in a manner of speaking.
“Well, you have beautiful breasts, Julie. You take after your mom. Hers are huge, too. Oh, shit. That feels so good. Don’t stop.”
I didn’t want her to stop, but I didn’t know if it was okay to cum on her hand. Guilt was plaguing me.
“Am I sick? You are my sister with my cock in your hand. And ever since I saw that video of Mom and Dad, I think about being in bed with Mom.” I omitted that I felt the same way about her.
“You are a normal guy, Sammy. You’re just frustrated. I’m happy to do this for you. I love doing this to my boyfriend, but I have to say, your cock is bigger and thicker than any I’ve seen, Sammy. I’m not a virgin. I’ve seen several, and yours is the nicest yet by a long shot.”
I admitted I was still a virgin. Julie just smiled and continued to stroke me until I came in her hand.
“It will happen soon enough, Sammy. I promise. And wow! That was quite a load. Remember, this is just between us. I actually enjoyed watching you cum. Love you, brother!”
Julie and I never actually had sex after that, but I continued to fantasize about both her and Mom.
So, on the morning of my eighteenth birthday, I awoke to the sounds of a pounding ocean surf as sunlight streamed through the partially opened window blinds. As I gripped my morning woody in a familiar ritual, I heard a gentle knock on the door, and then the door cracked open. I expected it to be Julie, but instead, my stepmother’s smiling face appeared.
“You awake, Sweetie. Today’s a special day!”
I released my cock in a panic.
“Sure, c’mon in, Mom.”
And then my stepmother stepped into my bedroom in our VRBO that sunny morning and changed my life.
“Happy birthday, Sammy. This is a special day for you, and I have a present for you that I think you’ll like.”
She was wearing only a pink lingerie top that highlighted her large, jiggling breasts. As she entered the room, they deliciously swayed with each step. That’s when I realized I could see right through the material. My eyes fell upon her huge nipples, displayed prominently through the thin fabric. She was wearing nothing but the top and a pair of sheer panties not covered by her waist-length teddy.
Instantly my pajamas bulged back to life as my cock straightened in rigid delight. The thin sheet covering me did little to hide my excitement. It tented obscenely, and I tried to cover it with my hands.
I couldn’t believe what I was seeing. My mother was practically naked in front of me.
“I know I’m not wearing much, Honey. I hope you don’t mind. I’ve been lying awake for some time, wondering how I could make today special for you, and I got myself all worked up thinking about it. Julie and I have been talking lately, and she told me you love to fantasize about my big boobs, so I thought, ‘What the hell. Sammy’s a man now.’ Tell me if I’m being too forward, Sweetie. I’m nervous just talking to you like this.”
I quickly offered reassurance that everything was fine. I patted the bed for her and sat up straighter as I adjusted the sheet to try to hide my erection.
In seconds, she was beside me, and she nervously held my face in her hands. Then, before I knew it, her lips were pressed to mine for a “birthday kiss” as she called it. At first, it was a motherly peck. Then she stopped and stared at me for an uncomfortable time, smiling. She brushed her shoulder-length, flaming red hair aside with one hand and then kissed me again with her freshly painted lips, but this time it was different. I tasted her lipstick as her mouth opened and her tongue found mine, snaking passionately, almost as if in desperation.
“I know you like big boobs, Honey. Are mine big enough? Go ahead and feel them. I love to have them touched.”
She reached down, grabbed my hand, and placed it on her breasts. I took the hint and fondled those magnificent orbs, her hard nipples pressing into my palm with only the thin nylon of her top between them and my hand. This was something i had dreamed of many times. A moan erupted from her throat, and then I felt a hand on my cock.
“Your father and I talked about this before he died. Don’t worry. This is something that he approved. I’m your mom, I know. But really I’m just your stepmom. There is a difference. We wanted your introduction to real sex to be a special event. And my goodness, you are already as hard as a piece of steel. It’s time you experienced the real thing, Sammy. You are a man now! I know you like to masturbate to relieve yourself, but today you are going to feel what real sex is like. I’m happy to be your first if you want. I would be your first, right?”
I nodded, and she removed the sheet covering my lap and gasped. A smile lit her face.
Together we slid my pajama bottoms off and my thick eight-inch cock stood proudly at attention. As she touched me, she explained what she was thinking in a husky voice I had never heard before. She leaned over and whispered in my ear, “Tell me what you would like, Honey. Don’t be shy.”
She tenderly kissed my forehead and then my lips.
“Talk dirty to me, Mom. That really gets me excited.”
I’m not sure why that popped into my head, but it did. And she complied.
She put her lips to my ear, and after first running her tongue lightly around the inside of it, she began using words I had never heard her use before.
“You have a beautiful cock, Honey. Just like your father. So thick and a nice length, too. My cunt is already wet just thinking about your big prick stretching me. I’ve secretly imagined this day for some time, and now that your father is gone, I need this as much as I think you do. Soon you’ll be sliding that beautiful prick in and out of your mother’s pussy. Wouldn’t you like to feel a velvety cunt gripping you instead of your hand? Doesn’t that sound wonderful? I know boys your age like to beat off, but this will be much better, I promise. But first, would you like to suck on Mommy’s big tits. Look how hard my nipples are. Yes, just like that. Should I take off my top so you can do that without anything between your lips and my titties?”
I nodded excitedly, and she slipped off her top, followed by her panties, and now she was completely naked. Her trimmed red pussy-hair matched her tresses.
There! Now we’re both naked. Isn’t this nice? Lie back and let Mommy show you how wonderful sex can be. We’re going to go slowly, Honey. Take your time, but if you have to cum, don’t hold back. Just let me know first if you can do that. I want to savor every second of this.”
My stepmom straddled me and let her big boobs dangle in my face while she wrapped her large pussy lips over my rock-hard cock and began sliding up and down the shaft. Her huge nipples by themselves filled my mouth, and I knew I was not going to last long.
As I sucked on her puffy areola and pencil eraser buds, I looked down to see her labia surrounding my thick cock as she slid her groin up and down my length. The combination of precum and pussy juice provided ample lubrication. My stepmom had a smirky smile as she alternately watched the action of her hips and my reaction to it. Occasionally, she bent down and kissed me, open-mouthed and moaning. I felt her hot tongue in my ear as she continued to whisper her feelings in a husky voice.
The sensations were indescribable. We continued in this fashion for several minutes, kissing and licking. The smile on my mother’s face said it all. She was in heaven, and I was in ecstasy. Occasionally, my cock head would start to slip into the opening I so desperately wanted, but each time my mother would adjust her hips so that I slipped out.
“Look how your big cock is searching for an opening into my pussy. I bet you’d like to feel the inside of my cunt, wouldn’t you? You feel so good just like this, rubbing against my clit. My big clitoris looks so tiny compared to your fat cock. But let’s try this….”
She raised her ass briefly, allowing my cock to rise just enough for her to slide forward and then back so that just the tip of my mushroom head could slip inside her moist opening. She held it there for several seconds, and then she moved her ass so that the entire glans was buried inside her.
I couldn’t believe my eyes. I was about to fuck my stepmom. I was going to lose my virginity.
“And there you are, Sammy. Inside your mother. How does that feel? I bet you’d like to feel more of me. You’re so thick, we’ll have to go carefully so you can stretch me out.”
She slowly sat back and we both watched as inch after my cock slid inside her tight channel. When her ass rested firmly on my thighs, she held it there. Her eyes were closed, and her lips were pressed together in a rapturous smile. Then she began to grind her hips. That was all it took.
“Oh, fuck, Mom. I can’t hold it. I’m cumming. Oh my god, that feels so good.”
“That’s it, Sweetie. Shoot all that hot cum in your mother’s pussy. I love to feel cum shooting in me. Oh, my! Mmmm, it feels like a firehose in me. You ARE excited, aren’t you?”
She wriggled her hips and squeezed me in tight circles as wave after wave of my sperm shot inside her. She wrapped her arms around my neck and pulled my face to her breasts. She held me so tightly I had trouble breathing for a moment, and then I felt her thighs jerk in spasms and her pussy clench my cock as the last of my cum jettisoned into her.
A sound I had never heard before came from her throat, and slowly, her spasmodic jerking subsided. She released me from her arms and kissed me passionately.
“Oh, Honey. You just made your mother cum. I haven’t felt that in some time.”
She ground her ass in little circles and pressed me to her breasts and then finally raised her ass slowly until my flaccid cock landed with a plop on my stomach. We both watched as a stream of my thick, milky, eighteen-year-old sperm drained out of her and onto my glistening shaft and balls. She wiped some of it with two fingers and, without thinking, tasted it.
“Wow, that was quite a load, young man! And tasty, too! You needed that as much as I did. Happy birthday, Honey. But the best is yet to come, so to speak.”
Almost as if on cue, there was a light rap on the door, and it opened with a squeak before I could say anything. My sister stuck her head in the room and with a fake frown, asked, “Well, what do we have here? It seems that someone is getting a birthday surprise. And by the looks of it, I’m too late. I can’t believe you started the party without me.”
My sister, Julie, stepped inside the room. She was dressed in a pair of loose pajamas with teddy bears printed all over them, but her gravity-defying pointed breasts certified that she was a full-grown woman. She walked over to the bed and first kissed Mom, then me.
“Happy birthday, you stinker. Did you enjoy Mom’s little surprise?”
“Oh, my god. This is the best day of my life. This is a vacation I’ll dream about forever.”
“Well, it isn’t over yet, you stud. The monkey is off your back, but let’s see if we can get him excited again, Mom. I’d like a little of that action as well. As long as we’re keeping it all in the family, don’t forget about your big sis. I have my own present for you Not to mention I get to play with that wonderful cock of yours again.”
So, after much hugging and snuggling, in no time we were all naked and groveling in my bed before Mom stopped us.
“As much fun as this is, why don’t we go to the master bedroom where we can spread out on a king-sized bed?”
Mother led the way and I took up the rear admiring the two asses sashaying in front of me. Mom’s was fleshier than Julies, but still beautiful as it jiggled with each step She had perhaps just a hint of cellulite but regardless, I imagined those fleshy spheres resting on my thighs as my cock stuffed the channel between them.
Julie’s nineteen-year-old ass was smaller and tighter, the result of running and yoga daily. Seeing it naked for the first time, I was not disappointed.
The master suite was huge, as was the bed compared to mine. Mom sat on one side and straightened out her legs as she patted the area in the middle.
“Right here, birthday boy. Julie, you get on the other side of your brother. Let’s see if we can get that rocket off the launch pad again. By the looks of it, it is refueled and ready for another…
