We all remember our first time. It’s an important, if sometimes cringe-worthy, milestone on the road to adulthood. Our minds replay the scenes again and again, as if from an old, favorite film. Here is my story.
The busy luncheonette adjoining the main concourse didn’t look too toxic. I dropped my duffle bag and slid onto a stool at the counter without anyone so much as looking at me. I take that back. A waitress slapped down a mug and, unsolicited, filled it with steaming black coffee.
“Back in a second, Hon.”
I pulled a menu from the metal condiments rack and stared at pictures of fried eggs, club sandwiches, and something called a Happy Waitress. I sighed, slid my wallet out of my faded jeans, and quickly glanced side to side before checking my cash for the third time since crossing the California state line. Traveling, even on a shoestring, was an expensive proposition.
“I recommend the lobster thermidor. The chef is famous for it.”
I spun around to face a smiling, well dressed woman in the booth behind me. On the table was a Town & Country magazine and cup of tea.
“Hah! Thank you for the suggestion. I was just about to ask for a wine list.”
She crinkled up her eyes and laughed
“My name is Jane. Why don’t you join me for dinner? I would adore company as charming as yours.”
I hesitated, not wanting this woman to think I was pitching for a free meal. I realized she had probably seen me counting the bills in my thin wallet. She persisted, however, and assured me that we could go Dutch. Maybe I just needed some human contact after an anonymous week on the road. I picked up my coffee and duffle bag and relocated to the vinyl covered bench across from her. I was curious to find out what someone like her was doing in a low rent bus depot in a sketchy section of Oakland.
Jane explained that she was there to pick up her niece, who was to spend the summer at her ranch near Napa. Apparently, the girl had missed her bus from Portland and would head out again in a few days. Jane had decided to have a cup of tea before heading home. At 18, anyone over the age of 30 was just plain old to me, yet I found myself drawn to Jane and her quiet, confident manner. She tended to purse her lips like a Cheshire cat and fix me with liquid, green eyes when she smiled.
Jane wore a simple beige blouse, sleeveless, that fell naturally whenever she moved. I guessed it was silk. A modest gold chain around her neck was the only jewelry she wore, save for a watch with a creamy leather band. Her slacks were black, which matched her gleaming loafers.
Everything about her was put together just so. Jane’s slender arms were tanned and toned. Wavy, shoulder-length hair was tastefully highlighted in soft, golden hues. If she wore makeup at all, it was imperceptible. There were just the faintest of wrinkles at the corners of her eyes.
As we chatted, I was surprised at how much she seemed to know about the life of American teenagers – how we dressed, the music we liked, our attitudes. She was remarkably candid about herself and told me that she had been married twice but never had children. She was 46, and liked to ski and ride horses.
“Helps me work out my frustrations,” she winked.
I felt myself blush at the moderately risqué remark and hoped that she hadn’t noticed. Jane was through with men, she said, at least as far as permanent ties were concerned. She lived with her best friend now – a younger woman named Callie. I wondered if Jane was telling me she was now a lesbian.
I was usually cautious around people I didn’t know well, but soon found myself answering her very direct questions about my romantic life. There wasn’t much to tell.
I had lettered in two sports in high school but always felt impossibly inadequate around the distaff sex. Although my buddies told me some of the girls at school liked me, I had never summoned the courage to ask any of them out. It felt good and a little exhilarating to bare my soul to Jane. She listened with a serious air and nodded as I tried to explain my shyness. When I finished, I guess I expected some comforting platitudes. Instead, she folded her napkin, fixed me with those green eyes.
“There are universal rules of attraction between the sexes. It’s all about animal instinct. You need to let that part of you go and follow the scent. Until you do that, you’ll continue to be frustrated.”
I was dumfounded. The look on my face must have been priceless because Jane started laughing. I was embarrassed, but also intrigued by her comment. I knew I hadn’t been the only sexually inactive kid in high school – far from it. Still, it seemed that the jocks I hung around with either had girlfriends or were at least comfortable talking and joking around with girls.
Jane asked what my next move was. I said I would catch a southbound bus and sleep during the ride. Hopefully, it would be the final leg of my cross-country trip to see my older brother in Long Beach. Nonsense, she said. Her place was only a couple of hours from here. I could sleep in the guest room, have a nice breakfast, and strike out again in the morning. I protested and we went back and forth for some time. Eventually, Jane had her way. Truthfully, the thought of clean sheets and a soft bed was pretty appealing. As we walked to her car, I noticed how petite and delicate she was. I fairly towered over her at 6’3”. We zoomed out of Oakland in her Land Rover.
We arrived at Jane’s house at about 7:30 PM. Actually, to call it a house would be an injustice. She lived in a gorgeous, mission-style ranch in the middle of wine country. I was surprised when a rugged looking young guy came out to greet Jane and take the car around to the garage. Jane hadn’t mentioned him at all. He nodded my way and said his name was Mike.
“Oh! Where are my manners? Chris, this is Mike. Mike is a house guest of ours. He’s staying with us for a while and helping us out with things,” said Jane.
Mike took the Rover and I followed Jane through the front door. The place was huge, with high ceilings. Music was coming from somewhere in the rear of the house so we followed it, finally going down a few steps to a large family room. Next to a huge fireplace across the room, a stunning woman with long dark hair rhythmically swayed her hips to a reggae tune while sipping a glass of red wine. She could have been in her late twenties; I really couldn’t tell. She was certainly a good deal younger than Jane.
I was again surprised when I saw two girls sitting on a couch playing a video game. Jane had neglected to mention them as well. One looked like she was about my age. She had a very pretty face and a thick mane of brown hair that I really liked. Her friend was, I don’t know, a few years younger – a skinny blonde waif, really.
“Jaaaney!!” squealed the dancer. She rushed over to give Jane an elaborate hug and a kiss.
“Callie, this is Chris. I met him at the bus station. He needs a bed for the night and so, well … here he is!”
“Chris. Wow! You’re tall. How old are you?” Callie extended her hand for a formal shake. Her smile was dazzling.
“I, uh … Eight-eighteen. Hi.”
Callie’s smoldering dark eyes, thick brows, and full lips had me completely tongue-tied. She wore short cut-off jeans with a loose fitting gauze top. The light behind her and the bounce in her blouse made it plain that she wasn’t wearing a bra. I could make out small dark circles under the material. Callie was tall, about 5’9” or 5’10” with long, smooth, slightly bowed legs.
“Girls, come over and meet Christopher,” said Callie. “This is Rachel,” she squeezed the older girl’s shoulder. Rachel shyly looked away as we shook hands.
“And this is our precocious Britt.”
The younger girl smiled under her white-blonde mop. Both girls wore long, cotton peasant-style dresses. I stole a glance at the mounds pressing against the material of Rachel’s frock.
“Oh, and have you met Mike?”
I turned around to see Mike leaning in the doorway with a beer in his hand. He raised it in salute. Mike was ruggedly handsome with dark features, deep set eyes, and wavy black hair.
“Let’s seeeee … yes … Dwight is finishing up some chores with the horses,” continued Callie. “You’ll meet him later.”
Who were these kids? I had gotten the impression from Jane that she lived here alone with Callie. Come to think of it, who, exactly, was Callie? Jane had said very little since we arrived, allowing Callie’s dynamic personality to fill the room.
Introductions made, Callie instructed Mike to show me to the room we would share for the duration, whatever that meant. She said tonight was Game Night but I should first get a nice hot shower and put on some clean clothes. Mike was pretty talkative and, as we walked through the long hallways, he quickly filled me in on the cast of characters.
Apparently, all the kids were strays of a sort. Jane always seemed to be bringing home someone new. After a while, the guests would move on, usually with some extra cash in their pockets. Mike had been here the longest of the current group, about three months. He was 20, a couple of years older than me. He had played football in high school before he took off on the road. I had noticed the muscles in his tattooed arms under the tight tee shirt. Mike was about three inches shorter than me but weighed at least twenty pounds more.
“Then Jane doesn’t really have a niece in Portland?”
“No!” Mike laughed. “She found me at the bus station, too!”
He told me that Rachel, 18, and Britt, 16, had arrived together about three weeks ago. Rachel had some sort of problem with her stepfather. She was very sweet, but extremely shy. Mike said she hardly ever talked, except to Britt. Britt was just a bundle of teeny-bopper energy. He wasn’t sure where she and Rachel had connected but Britt’s goal was to tag along with a touring band in San Francisco. Dwight, who I hadn’t yet met, was a 19 year old kid who had come from a pretty tough part of L.A.
“So what’s the deal with Jane and Callie?”
“Well, this is Jane’s house. She’s loaded, you know. But Callie rules the roost, here. She calls all the plays, except when it comes to Rachel. They met when Callie was a student in college - some kind of track star - and Jane was an assistant professor,” Mike continued. “Jane just threw a massive blowout for Callie’s 30th birthday last week. There were tons of people here. Shit got pretty wild.”
This was a lot of information and I must have had a pensive look on my face. Mike smiled and punched me hard on the shoulder.
“Relax,” he said. “We have a pretty good deal here. We do some work around the place and, well, keep the ladies entertained. You just need to get used to the lifestyle. You’ll see!”
Mike turned to leave as I headed into the bathroom for my shower.
“Wait,” I said. “What the hell is Game Night?”
“Oh, it’s just something Callie cooks up about once a week,” Mike giggled, “It’s different every time and you never know what the rules are. Everybody plays, though. I guess that’s the one rule that never changes. Callie’s Rule.” He smiled, “Dude, just try to relax and roll with it!”
Callie was right; the long, hot shower felt great. I dried off with a big fluffy towel and walked into the bedroom. Laid out on the bed was a pair of while cotton gym shorts. A handwritten note was on the pillow: “Took your things to the laundry. See you downstairs! Love, J”. Sure enough, my duffle bag was empty. Even my ratty old sneakers had disappeared.
I pulled on the shorts, which felt pretty skimpy. They weren’t the baggy, nylon basketball shorts I was used to. I looked around and there wasn’t a shirt to be found. I thought about going through some drawers to look for one but didn’t want to mess with Mike’s stuff. So I walked downstairs wearing the shorts and nothing else. I felt really weird not wearing any underwear beneath the flimsy garment.
When I rejoined the group, it was already getting dark and there was now roaring fire in the large fireplace. Some kind of techno music was playing in the background and I could feel the percussion of the bass. I was startled to see that everyone had changed their clothes, too.
Mike was wearing shorts nearly identical to mine, as was the thin, athletic-looking black guy standing next to him. Neither one wore shirts. That put me a little more at ease. The two girls were dressed in black three-quarter length tights, plain white cutoff tee shirts that exposed their ribs and tummies, and little white half socks. What kind of games were we going to play?
My eyes almost popped out when I saw Jane. She was standing at the bar just a few feet away from me pouring wine from a decanter. She had on a white sleeveless micro-fiber top that accentuated every detail of her upturned, pear-size breasts. I could see little impressions where her nipples pushed against the stretchy fabric. There was no evidence of an undergarment. My gaze trailed down past her exposed belly button to a pair of hip hugging black Lycra compression shorts that started barely above her, um, private area. Her body looked more like a teenager’s than a forty-something. Realizing I was staring, I looked away, embarrassed.
Callie was the first to say anything.
“Welcome back, big guy! I don’t believe you’ve met Dwight,” she motioned in the direction of the two boys. “Feel up to playing some games?”
Once again, Callie had me speechless. She stood directly in front of me wearing a diaphanous white top that went to her waist. Beneath it was a white, spaghetti strap bra with a red and pink floral print. A matching cotton bikini bottom completed the picture. I was confused, aroused, and shocked that she would display herself like this. The panties didn’t hide the swell of her mound down there and I couldn’t help notice a dark triangle beneath. I just couldn’t take my eyes from her womanly hips, flat stomach, and narrow waist. Her boobs, while not huge like the girls in Playboy, were round and heavy enough to test the delicate bra.
“Why don’t you have something to drink? You look dry.” Callie looked up at me down, running her warm hands over my shoulders and biceps. “My, we didn’t realize how well put together you are!”
It was true; I had very broad shoulders. It was a family trait. And lately I had been admiring the lean muscle I had packed on them.
Mike walked over and handed me a Heineken. It was then that I noticed that underaged Britt was sipping a glass of white wine. I didn’t know what was going on here but it was clear that the usual rules didn’t apply.
Dwight came over to bump fists with me and ask about my trip but I still felt like a fish out of water. It was like everyone was watching me, even though they resumed their conversations and sipped their drinks.
Next, Britt took me by the hand, and guided me to a seat between her and Rachel on the couch. To say that I was self conscious is an understatement. For one thing, I couldn’t quite find a way to sit that didn’t cause my thin shorts to ride nearly up to my crotch. Sitting next to the lovely Rachel, with her flowing hair and lithe body, drove me to distraction. I smiled at her and took a big gulp of beer, trying not to look down at the long slender leg that was touching mine. I was glad that I had taken a shower and at least smelled good.
Even sitting next to the 16 year old had me feeling funny. Britt still held my left arm and she was now playfully rubbing her foot on top of mine while she peppered me with all kinds of questions. I was starting to feel a familiar flutter in my groin.
After a few minutes, Callie tapped her wine glass with a spoon.
“Attention, ladies and gentlemen. Tonight we play Lady’s Choice.”
Britt shouted a whoo-hoo and clapped her hands over her head.
“But since we have a new guest,” Callie continued, bowing slightly in my direction. “We will allow him the honor of the first round.”
I had absolutely no idea what this woman was talking about, but Britt put her hand on my back and started pushing me forward. I looked at Rachel; she raised her eyebrows a bit, gave me an encouraging smile, and nodded toward the front of the room. I got the message and stood up, stepping in front of the gathered audience.
“Now, my choice for your first opponent is your new best friend, Mike.”
Mike got up and moved next to me. Opponent?
“Good sirs, the rules of the tournament are simple; with every contest there is a champion. And to the champion goes the prize.”
Callie rolled back her shoulders and let the sheer teddy drop to her feet.
“And I am the prize,” she beamed.
“Wha-what? What are we supposed to do?” I asked. My head was swimming.
That’s when a ton of bricks hit me in the ribs, sending me to the floor. Mike was on top of me grabbing my wrist and trying to pin it over my head. His chunky thighs clamped around my left leg like pliers. So this was the game. I didn’t want to play but Mike was trying to make a pretzel out of me. I bucked up my hips to get some leverage beneath him. Man, was this kid strong. Mike’s right arm supported most of his weight so I knocked it away and slid out from under him. I tried to get on his back to hold him down but I wasn’t built for wrestling. Mike rolled his compact body over and managed to get on top again.
As we wrestled, I heard clapping and encouragement from our audience. I was quick but he was strong. After about five or six minutes of tumbling around on the Persian carpet – it seemed a lot longer – Mike was able to get me in some kind of hold. His body was pressed up against my back and – oh, my God – he had a hard on! What’s happening? Is Mike gay?
Just then, I heard three loud slaps on the floor, “One! Two! Three!” Callie stood over our heaving bodies and declared Mike the champion. He stood up and offered his hand. I thought for a second about kicking him in the balls. But, no, he beat me fair and square. Besides, I couldn’t care less who the winner was. I just wanted to get out of there.
We stood next to each other, breathing heavily from the bout. Our shorts were all but torn off and I tried to adjust mine. I looked down and saw the pup tent in Mike’s shorts. Oh Jesus, this would be bad.
Callie stood in front of us as Mike and I faced the others.
“Mike has won the prize – yours truly,” she curtseyed to more applause. “Now let these brave knights show us their lances.”
Mike dropped his shorts and stepped out of them! A hard dick stood straight out in front of him, bouncing slightly from the movement. I couldn’t help but look. It wasn’t very long but it was super thick and powerful looking. A mass of dark curly hair completely hid his balls. Mike reached down and pulled back the skin on his rod, away from a massive, uncircumcised head.
Callie smiled at me, “Christopher?”
WHAAAT?!! My breathing was labored and my chest felt heavy. Part of me wanted to run but I just couldn’t move. I felt alarm and arousal at the same time. I knew there were six sets of eyes waiting for me. I looked at Jane and remembered she said about letting go.
Slowly, my shaky hands pulled the shorts over my narrow hips and let them drop to the floor. I kicked them in front of me as Mike had done. My nipples tingled and hardened as the air hit my genitals. I could tell without looking that my cock was hanging low between my legs. I felt blood beginning to swell it. I followed everyone’s stares to my dick. I wasn’t hairy like Mike. I had a triangle of brown pubic hair but nothing on my balls, abdomen, or chest. I didn’t know how I felt about not being completely hard like Mike but I could see that, even in this semi-soft state, my dick was a lot longer than his. That gave me at least some measure of comfort.
Jane got up and stood beside me as Callie stepped back. Her eyes surveyed my nakedness while and she placed a hand on my left buttock. I flexed involuntarily and warmth radiated in my chest cavity.
“Chris, I told Callie and the others that you’re a virgin.” I looked at her. “That’s okay; it’s nothing to be ashamed of. You’re nervous right now and you may be experiencing some performance anxiety. It’s perfectly natural.”
I couldn’t believe what I was hearing. Did she have to tell everyone? Even the two high school girls? Jane continued talking as she squeezed my tight ass muscle.
“Mike is going to penetrate Callie now, since he won the match. But first these ladies need to see you good and hard.” She turned her head toward the couch.
Penetrate?? Hard?? My heart jumped when the 5’5” sylph stood up and walked over to me. Alarm and outrage mixed with excitement. She smiled demurely as she rose up on her tip toes and placed a hand lightly on my chest for balance. I instinctively bent my head to meet her mouth and she kissed me softly – my first real kiss. Her lips were soft and sweet. I died when her tongue gently slid into my mouth to find mine. I felt a pulse in my cock to match my heartbeat. One hand went to the bare small of her back and pulled her closer. I slid the other up and under her shirt, exploring her warm, braless back. She smelled fresh and clean.
Then she did something that floored me. Rachel took half a step back, took my penis in her right hand, and sort of held it across her open fingers as if she was weighing it. Then she took the darkening head between her left thumb and fingers, gave it a gentle tug, and began to knead and twist it. It was like an electric shock! Rachel’s right hand closed over the growing column. I saw the member surge and thicken right in her hands as she worked it.
Jane looked down between us and announced, “Oh yes, he’s going to have a nice erection.”
Within ten seconds, my boner was rigid and pointing toward the ceiling. My circumcised head was swollen and gleaming with a drop of liquid from the slit, its ridge almost blue. My shaft stretched its thin skin as it strained upward. I had never been so aroused. Rachel let go and stepped back with her lower lip between her teeth and an apologetic smile.
“Ooooh, I love how it sticks straight up like that! He’s got a long one!” chirped Britt.
I was beyond shocked at this point; shocked at their behavior, and my own. Callie motioned to Dwight.
“Dwight, why don’t you join the other boys?”
I hadn’t noticed until then, but the elastic on Dwight’s shorts were pulled completely away from his flat belly due to an obvious hard on. Smiling, he moved next to me and pulled the shorts to his ankles, springing free a long, black boner. It curled slightly upward with a very slight list to the right.
“Isn’t it amazing haw many sizes, shapes, and colors the they come in, ladies?” asked Callie. “And every single one is a marvel!”
She moved in front of Dwight and me and gently handled our erections. I tensed up and held my breath. I could hear Dwight breathing deeply.
“Well, Chris is definitely longer than Dwight, by about half an inch, maybe more. It’s a very good size – we’ll measure him later. He’s cut, obviously,” she continued matter-of-factly. “Dwight has a nice fat head and his balls are bigger, but Chris has a little more girth on his canon. You brought us a nice stud, Janey!”.”
I was humiliated and thrilled at the same time. I felt like a horse on the auction block and my heart was racing. Callie stepped away and I saw Jane, Rachel, and Britt running their eyes over my naked body.
“But Michael, you know I just love your sturdy road paver.”
Callie held her hand out to Mike, who took it and led her to a large sectional sofa a few feet away from us. I noticed that it had been rearranged to form a giant rectangle. As she walked away from me, I got my first good view of Callie’s spectacular ass. Nice round globes moved beneath her panties. She was nearly the same height as Mike but he was thickly muscled while she was long and slender.
Mike stepped behind her, released the catch on her bra, and threw it on the floor. Her breasts fell out and bounced right back. Callie’s pink nipples popped out like erasers and I could see goose bumps on her arms and legs. Transfixed, I held my breath. Again, as much as I wanted to leave, I found that I couldn’t. The entire demeanor in the room had changed as everyone watched Mike take control of Callie. He snapped the elastic of Callie’s panties.
“Take em off.”
Callie compliantly bent over and she carefully slid her underwear over one foot and then the other. Mike’s engorged phallus poked the crack of her ass as she did this. Before she could straighten up, Mike shoved her hard and Callie landed on the cushions with her elbows bent. Mike kicked her feet wide and I could see her pink, fuzz covered slit. A clear, viscous fluid leaked along the channel.
Mike moved forward and, with his hand, moved his enormous mushroom head up and down the wet vagina. Callie moaned and shook as her darkened labia gave way to the motion. Her puckered anus was clearly accessible so Mike slid his glans over that as well, soaking it with Callie’s own juices.
I looked over at Rachel. She was watching the couple intently with her legs crossed tightly, rocking her pelvis slightly. A finger absently traced patterns over her breast. She must have sensed my stare because our eyes met for an instant. Her eyes dropped to my aching, turgid penis and she smiled before turning back to the developing scene. Her young friend, Britt, had a hand jammed right down the front of her tights, moving it rhythmically under the stretchy black fabric.
“Please fuck me now, Mike,” Callie hissed. “I need to be fucked hard with that fat cock.”
Callie was positively trembling now. Her knees were up on the sofa; her head and shoulders were pressed down against the cushion. Callie arched her long back, pushing her ass in the air. She was completely vulnerable to Mike.
I didn’t know how that unyielding, massive thing would fit into her silky, narrow entrance but Mike held Callie’s hips and began to press his pelvis forward. Callie’s lips succumbed as Mike steadily plowed ahead. She yelped in surprise as he brutally buried himself all the way into her. Mike started pumping with his slimy, thick thing while she shook, and cursed, and pleaded for more. The walls of her vagina moved in and out with his strokes and the musky aroma of her cunt filled my nostrils.
Suddenly, Callie’s muscles tensed and rippled. Her head flew back and staccato breaths issued from her mouth as an orgasm overwhelmed her. Long strands of hair stuck to her sweaty forehead and back. It was magnificent.
“Ahhhh, I’m gonna come,” groaned Mike.
Mike’s quivering tool pulled out of Callie with a sucking sound. To my shock, Britt appeared at his side and took the slimy phallus in both hands. She was shirtless now with erect nipples popping out from little breasts that were more developed than I would have guessed. She held the wide base with one hand and started pumping the stout shaft with the other. Mike’s buttocks clenched and she pulled his skin all the way up to the bulbous head, tweaking it with her thumb. She pulled back hard as great airborne strings of semen splattered up and down Callie’s back. Britt held Mike’s hairy balls as she continued to pump the last drops of cum from his cock.
“No getting soft, Mike,” Britt warned while pulling off her tights.
Naked, she knelt and began to lick Mike’s cum and Callie’s secretions off his dome. The meat was too wide to get her hand completely around, yet she had complete control of him. She jammed her pointy tongue into his still leaking slit and kissed the sensitive underside. I couldn’t help getting turned on by the sight of that sixteen year old body in its early stages of maturity. Britt’s round butt protruded nicely, her thighs were lightly muscled, and her mons was covered with wispy golden hair.
“That’s my good fucker. You’re a good hard boy,” she said. “You want to fuck Britty’s little pussy, don’t you?”
I couldn’t believe my ears or my eyes. By this time, Callie has risen from the sectional and walked naked past me to where she had left her wine glass. She looked at me and then Jane.
“Leave some for me, Janey. I’m gonna work him hard when it’s my turn.”
Rachel appeared with a moist towel and gently cleaned Mike’s semen from Callie’s back, butt cheeks, and crotch. The three women were looking at me. I sensed, very strongly, that much would be expected of me before the evening was out. Rachel gave Jane a questioning look.
“Sorry dear, I found him,” said Jane in answer to the unspoken question. “Besides, it’s age before beauty!”
Jane wrapped her arm inside mine and guided me toward the sectional playground next to Britt, who was still torturing Mike’s now purple sledge. Jane stopped, faced me, and raised her arms in the air.
“Undress me, please.”
It is difficult to describe what I was feeling – excitement, fear, nervousness, lust. I started shaking as a shot of adrenaline hit my bloodstream. Until this evening, I had never even kissed a girl. I placed my hands on the smooth, warm skin of Jane’s ribs and slowly slid them up her sides and under her uplifted arms, taking the Lycra top up and over her head. She gave me an approving smile as her little breasts bounced freely and long, finger-like nipples pointed up at me. I couldn’t help myself. I gathered one in each hand and rolled the pink erectile tissue in my fingers.
Jane let out a long breath and shuddered slightly before turning around, patting her behind. I understood the instruction and pulled the compression shorts to the floor. This left me crouched behind a small round butt. Her legs were parted just enough to give me a view of her prominent pussy lips. I reached up to gently massage and pull her soft cheeks apart, revealing the darkened circle around her sphincter. A dusting of fine blonde hair covered Jane’s thighs and the small of her back. I couldn’t believe this refined 46 year old lady had me strip off all her clothes with the intention of letting me defile her.
Rachel walked up to us with Dwight in tow and kissed Jane deeply on the lips. Jane fixed Rachel with her eyes.
“Get your clothes off.”
Dwight removed Rachel’s top as the girl quickly stripped off her tights and socks. She was a good two inches taller than her mistress, with fuller breasts and brown nipples that popped out like thimbles. She had the legs of a thoroughbred, muscled buttocks, and narrow hips. At eighteen, she was physically mature, but with a young girl’s colt-like aspect. The obedient, naked girl was the same age as all the girls I had been afraid to approach. She could easily have been sitting next to me in Chemistry just a few months ago.
Jane placed her hand over Rachel’s hairy vulva and slid her middle finger deeply into the girl’s vagina. Rachel went weak at the knees before gathering herself. Jane removed her glistening digit.
“Chris has her dripping like a bitch in heat,” she said to Dwight. “I want you to eat her pussy and lick her asshole, but don’t fuck her and don’t let her come.”
“You can suck him off if you want. He’s been very patient this evening,” she said to Rachel.
Turning to me, Jane smiled broadly and put her wet finger to my lips, giving me a taste of Rachel’s young pussy. It was as if I had inhaled a line of cocaine. I stood, pulled Jane close, and lifted her up. Jane’s legs wrapped around my hindquarters and my hands held her up by the ass. I felt my penis rub against her wiry, neatly trimmed bush. My only thought now was to get inside her. As our open mouths met, I backed up until my legs hit the sectional and I plopped onto the cushions with Jane on top of me.
I landed a few feet from Britt, who was now lying on her back with her knees splayed wide over Mike’s muscular arms. He lifted her little ass in the air with his hands and drove his tongue deep into her squirming pussy. She was still encouraging him in the most profane of manners and twisted her hard little nipples in her fingers.
Jane stretched out next to me with both hands stacked on my erect pole. Our lips were still pressed together as she moaned:
“Oh, I want this big virgin bone inside me…”
I played with her tits and nipples as she squirmed and jacked me with hot hands. Jane kissed her way from my throat down to my chest and stomach. Then she was crouched between my knees, pushing them wide. I groaned as she bathed my cock head with her hot tongue. The sensation was so intense I nearly had to pull away. I looked down in time to watch her full lips slide over the swollen bulb and halfway down the shaft. Her mouth was warm and her lips were soft. Jane’s tongue feathered the underside of my dick while she glided up and down my pulsating member.
I felt a thump to my left. Rachel had plopped onto her back and her face was just inches from mine. On a whim, I leaned over and kissed her, gently sucking her lower lip. She pulled back with a surprised smile. Looking down, I saw that her legs were draped over Dwight’s shoulders. His head was buried in her dark bush and she was squirming in obvious pleasure. She giggled and leaned in for another kiss, this one a long steamy affair, as the two of us were serviced orally by our partners. It was the most intense moment of my young life.
Jane was an expert at the practice of fellatio. She seemed to know when I was at the brink of exploding in her mouth. Several times she backed off and allowed the pressure to subside, only to start over again by sucking on my tingling head.
Frustration and anticipation mounted. Eventually Jane disengaged and began to crawl up my body like a cat, knees and hands on either side of my rangy frame. We kissed again deeply as Jane’s golden hair fell across my face. A slippery pussy pressed my tumescent erection against my body and ground up and down its length. My fingers dove into the crack of her ass, exploring her puckered button and slippery labia. Jane groaned in my mouth without breaking contact. Everything was warm and wet and wonderful.
To my right, Britt was letting loose loud sounds that were a cross between euphoria and pain. He body was completely off the sofa, except for her shoulders and head, and was stiff as a board. Mike frantically rubbed his big tongue between her legs where she held two spread fingers.
I felt movement to my left as my fingers pushed deeper into Jane’s crevice. Dwight had pulled Rachel closer to him and was now on his hands and knees above her. His rigid snake was centered over her face. As he lowered his hips, Rachel’s tongue slid out to accept his super-elongated, mahogany-colored head into her mouth. Dwight moved slowly in and out and I could see the glistening trails of Rachel’s saliva on the dark shaft. With each movement, she took more of him. It was hard to tell who enjoyed it more. Rachel fondled Dwight’s testicles, the size of lemons, and fingered herself with her free hand.
Jane was driving me crazy by sliding her moist pussy up and down my burning shaft. I couldn’t take any more. I quickly flipped our bodies over and she grunted as I slammed her back against the cushions. Poised above her, I pushed out the inside of her knees with my own, opening her sex completely to me. Rachel and Dwight turned to watch us as his lubricated instrument was suspended inches above her face.
Jane took my penis in hand and aimed it down to her crotch. I lowered my hips and she slowly rubbed the head up and down the narrow slit just inside her labia. I watched curly pubic hairs grab and release it as the knob traveled up and down. I had never felt anything like this. Then Jane positioned me at her opening and placed her hands lightly on my hips as she drew up her knees to my sides. I began to press downward. This was finally it.
“Take it slowly,” she breathed, “You’ll come quickly the first time but that’s natural ... We have all night.”
As I pushed, I felt her flesh resist slightly and haltingly give way as it adjusted to the girth and shape of my cock. She exhaled under me when I went as far as I could and began to pull slowly back. I repeated the slow stroking motion, loving the warm, snug fit. Jane’s hips were moving with me now and rising up to meet me as I pushed deeply into her. I pulled too far back once and my dick sprung out of her. I heard Rachel giggle but Jane deftly reinserted my virgin penis. Now I started pumping harder and Jane matched the effort, breathing harder now.
“Oooh, you’re hitting my cervix.” She whispered.
I froze. “Am I hurting you?”
“No,” Jane smiled. “I like how you fill me up, Chris. Go harder now. Don’t be afraid to fuck me.”
I started jacking my hips and ramming my oak in and out of Jane. Legs tightened around me and I felt a familiar pressure building quickly in my groin. I exploded and pumped what felt like a gallon of hot seed deep into Jane’s body. Relief and pleasure coursed through my body like a drug.
“Don’t stop,” panted Jane. “I’m going to come. Keep going … Harder ... There ...”
I shifted forward and drove down into her over and over, pushing her petite body into the cushions with the force. Jane’s fingers raked my back. Suddenly, everything tightened around me as Jane fused her shaking, skinny body to mine and began to grunt loudly and invoke name of the Lord. Slowly, her body relaxed and Jane just lay there smiling up at me.
“So, Chris, was it worth the wait?”
“I can’t believe it,” my chest was heaving. “Thank you.”
She crinkled her eyes and laughed. I was kneeling between Jane’s legs, looking down at her naked, sweat covered body. Her hair was a tangled mess, her pubes were matted and sticky, and her nipples poked up at me. To me she looked beautiful. My slowly deflating phallus, still thick with blood, was covered with viscous fluids.
“That was hot, Chris,” Rachel spoke for the first time. “Congratulations.”
She and Dwight were smiling at me. I then felt bare skin against my back and two long arms wrapped around me. Callie’s dazzling smile appeared as she peeked around my right shoulder.
“Mmmmmm …that WAS hot, you two,” she cooed. “Nice maiden voyage!”
Jane squeezed my softening charger and kissed me on the mouth before hopping off the sofa and heading across the room. Callie moved in so we now knelt facing each other with my dick swinging long and heavy at rest. Her round boobs swayed provocatively with dollar size areolae beaming up at me. I cupped a hand over her vulva, as I had seen Jane do to Rachel, and slid my middle finger into her compliant vagina. Callie panted lightly and her boobs transformed before me, nipples growing visibly hard. I lifted a breast and lowered my head to take a half inch long nipple into my mouth. I sucked and rolled it over on my tongue while Callie groaned and ran her hands through my hair and over my shoulders.
“Ooooh, you’re learning to be a bad boy, aren’t you?” she whispered.
I lifted my head and pulled Callie’s chest against mine, running my hands freely over her back and ass.
Rachel had resumed ministering to Dwight. His lean body stretched above her in a plank position now, while she sucked on his bomb-shaped head. Her cheeks billowed in and out while one hand jerked his boner rhythmically. Dwight’s scrotum and testicles had contracted, forming a huge, blue-black lump at the base of his stiff penis. Dwight let out a gasp, his body stiffened, and his buttocks clenched as he announced he was coming. Rachel stroked faster, her mouth filled with dark meat.
“Baby, I’m coming!”
I could see swallowing motions in Rachel’s slender throat. Dwight jerked repeatedly and trembled before falling next to her in a heap. Rachel remained on her back with tiny rivers of thick white cream escaping the corners of her mouth.
Watching the lithesome teen service the black stud so completely with her mouth while I held Callie’s soft body against me, brought a familiar stir in my penis. I felt myself growing, soon pressing urgently against Callie’s belly.
“Back so soon?” giggled Callie, as she reached between our bodies to feel the resurgent member. “I love teenagers.”
I took Callie’s shoulders and started to push her down onto the sofa. She placed her hand firmly against my chest and stopped me.
“Patience, lover, it’s not my turn.”
I blinked at her, uncomprehendingly. I had gone from diffident, self-conscious virgin to a hungry-for-sex predator in the space of an hour. I needed to have her right now.
“It’s MY turn.”
Surprised, I turned around to see the 5’3” Britt standing over me. Her flaxen pussy was inches from my nose. The sixteen-year old sat down, leaned back on her hands and spread her legs.
“Come here and lick me, fucker.”
Stunned, I crawled over to her open crotch and brought my face down to her little cunt. Britt’s rose-colored inner lips were open slightly, like the petals of a flower, and glistening with her secretions. I placed my tongue inside her labia and took in the musky-sweet nectar. My tongue moved easily up and down, drinking in her juices. Nearing the bottom, I felt her opening.
“Up here,” she instructed. “Softly. Get your tongue good and wet.”
Two of her sticky fingers were spread, giving me access to the little hood at the top of her labia. I flicked at it gently.
“That’s it, little circles.”
The teenager moaned as I followed her verbal cues. I put my lips over it and sucked generously and pushed a finger into her vagina. She squirmed, lifted her hips, and moaned louder. The hands on my head and movement of her pelvis provided all the feedback I needed now.
Suddenly, Britt pushed my head away from the delicious feast. She pressed her fingers on either side of the fleshy structure and out peeked a glistening, white-pink pearl.
“Right there. Easy.”
I carefully applied the very tip of my tongue to the slippery clit and pushed down on it. The reaction was immediate. Britt threw her head back and her body stiffened as if her body was attached to a live wire. I continued to work my finger inside her. I moved my tongue in a circle, pressing directly on the fattened nub. Britt’s slender thighs clamped down tightly on my head.
“Ohhhhhhhhh, God … ohhhhhhhhh!”
After thirty seconds of contorting her body and cursing, Britt shoved my head away from her bush. She lay on her back, breathing heavily. I was intoxicated by the taste and smell of her most intimate place and I loved that I could give her so much pleasure with my mouth. She seemed much older to me now. I was again aware of my throbbing bone. I wanted to fuck again.
To my right, Dwight had meanwhile mounted Callie and was plumbing her with long steady strokes.
To my left, Jane sat on Mike’s chest, applying liberal amounts of lubricant to his upright phallus. I wondered what she had in mind for him.
“It’s finally MY turn,” purred Rachel, crawling toward me with a surprisingly mischievous smile. “Jane said you’re MINE now.”
I was still kneeling between Britt’s legs when I had turned to the sound of her friend’s voice. Without warning, Rachel lunged at me, like a panther onto its prey. I fell backward with Rachel on top of me as Britt rolled out of the way. Rachel was in a frenzy.
Our mouths found each other and she clamped a hand around my rocket. The acrid taste of Dwight’s ejaculate was still on her lips and tongue. I was surprised that I didn’t mind it. Rachel ground her vulva into my hip. Matching her passion, my hands ran down her back and over her writhing ass. I needed to get into that smoking body.
“Oh, I’m so horny, Chris,” she groaned. “I’ve wanted you all night.”
I was stretched out on my back now and Rachel sat on me, her thighs spread wide. My stiff cock stood upright against her belly, past her navel. She put her hands on my chest and raised her round hind quarters in the air. Droplets clung to the dark tangle of pubic hair as it hovered over my rock-hard erection. Rachel centered my tool and slowly began to sink down onto it. I could feel every slippery muscle in her tight tunnel as she carefully impaled herself on me, inch by inch.
Rachel leaned forward, toward my head. I held her tender, swaying breasts and rolled plump, burgundy nipples between my fingers.
“Oooooh, I love that, Chris.”
Over and over, Rachel traveled the length of my willing slave to the limit her body would allow. I looked down to see her pussy stretched wide around the wet appendage. Now she had most of her weight supported by her hands on my heaving chest as her ass and pelvis pumped faster and faster, forcing me through her tight vagina. I reached around to dig my fingers into her crack, feeling her power and urgency. I thrust my slave upward to meet her assaults.
“I’m gonna come, Rachel”
“Me … ohhh. … me too.”
We both convulsed as I pumped white hot semen deep inside Rachel. When our orgasms subsided, I could tell we were both completely spent.
Rachel lay on top of me dripping in sweat as my dick slowly relaxed inside her. It was a nice feeling. Her smell was a sweet mixture of sex and her natural fragrance. We kissed deeply and murmured sweet compliments to each other. I closed my eyes and breathed deeply.
“BREAK TIME, BOYS AND GIRLS!”
I opened my eyes to see Callie looking down at us.
“You’ve got thirty minutes to recover, lover. It’s CALLIE’s turn next!”
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