The Package (What would you do?)
A misdelivered package results in a good time.
A misdelivered package results in a good time.
The long awaited spring break comes an Mrs. Logan helps us out.
The first time I had sex was with my Aunt Ellen. I was 12, and she was 41. My parents went on a trip for four days and asked my her to stay at our house to watch my sister and I. I had never really fantasized about my Aunt, but more than once I had tried to look down her top or up her skirt. Even though she was over 40 and fairly plump, I remember that she had nice big boobs that jiggled when she walked, a sweet round ass, and was very attractive overall. Her husband had died about 3 years earlier, and although she was very attractive she had not started dating again and I’m sure had not had sex in over 3 years. At 12 I was really starting to get interested in girls and spent alot of time jerking off and fantasizing. Little did I know that my dreams would come true that week!
The day that Aunt Ellen arrived and my parents left for their little getaway, things were pretty normal. My Aunt and sister and I had dinner together and caught up on things. Aunt Ellen lived a few states away in the Midwest, so we only saw her a couple of times a year. After dinner, Aunt Ellen had some wine while my sister and I took our baths and got ready for bed. It was a humid summer night and after tossing and turning for a couple of hours, I got up and went into my parent’s bed (theirs was the only room in the house that had air conditioning back then). Aunt Ellen was already asleep, so I quietly slipped under the cool covers and fell fast asleep myself.
Sometime in the middle of the night, I awoke while having a vivid wet dream. In my dream, one of the cheerleaders at my school was letting me feel her pussy. In my half awake/asleep state I slowly realized that my young cock was rock-hard. Then, as I came to my senses I realized that it was poking at something warm and squishy — the crack of my Aunt Ellen’s ass! She was laying with her back to me, and somehow her nightgown had worked itself up above her waist. It was then that I discovered that my Aunt Ellen was not wearing any underwear and my rigid cock had happily poked out of my boxer shorts, wedged itself between her legs, and was now prodding at the area between her anus and pussy. My precum had already made the whole area slippery. She was still asleep, and I was frozen in fear that she might awake and find my cock between her legs. I laid still for what seemed like forever, hoping that my cock would soften and I could pull away. But no, it stayed right there throbbing happily against my Aunt’s warm, plump folds.
While I was trying to decide what to do, she suddenly stirred, shifted on her pillow a bit, drew her knees up and arched her back slightly towards me. I held my breath until I was sure she was still asleep. But then I had a new sensation — the new position she had shifted into had caused the tip of my cock to move directly into the juicy opening to her cunt. No longer in control, I pushed forward slightly and felt the head of my cock slip between her pussy lips. I can still remember that incredible feeling — the first time my cock touched sweet soft pussy flesh. Completely forgetting that the pussy I was entering was my Aunt Ellen’s, I pushed forward a little more and without warning starting squirting cum into the opening of her cunt. I immediately pulled back in horror and shot my remaining streams of cum on her ass and the bed. Quietly, I slipped out of bed and hurried to my room where I laid awake worrying about what would happen to me the next morning when Aunt Ellen discovered dried cum all over her ass and pussy.
In the morning I was a nervous wreck. I tried not to make eye contact with Aunt Ellen when she summoned me downstairs to breakfast. To my surprise, she made no mention of the night’s events and acted as if she was completely unaware that I had even been in bed with her. Was she too embarrassed to talk about it?, I thought. Finally, I decided that she had slept through everything, had not noticed the cum and went straight into the shower unknowingly washing away the evidence!
All that day I couldn’t stop thinking about what had happened. After an uneventful dinner, Aunt Ellen was again having some wine and watching a movie as my sister and I went off to bed. I had no chance of sleeping, as I laid in bed playing with my cock and trying to get up the courage to get in bed with my Aunt again. After about 2 a.m., I crept into her room and once again slipped quietly under the covers. As I cautiously moved closer to her, my hard cock brushed against her naked butt cheeks. Was her nightgown pushed up above her waist again, I thought? No — as I lightly slid my fingers from her ass up her back to her shoulders it was clear that she had gone to bed totally nude! Seizing the opportunity, I carefully reached around her and cupped one of her huge tits in my hand. The feeling of her large, soft boobs and her hard nipple in my palm made my cock throb even more. I gently squeezed her tits while my cock once again probed between her cheeks. Just like the night before, she shifted again and gently pushed her ass and pussy back towards me. I thought that maybe in her sleep she was subconsciously aware of a cock pushing between her legs and involuntarily shifted to allow it entry. Once again, I felt the head of my cock probing her juicy pussy opening. This time, though, I pushed forward slowly until my entire length was inside of my Aunt. I held it there for a moment, savoring the feeling of her large, warm cunt. Then, I lightly cupped her tit and began gently moving my cock in and out of her. Before long, I could feel myself ready to cum again. Thinking quickly, I decided that it would be too risky to cover her ass again and if I quickly pulled out and came in my hand I might wake her. I pushed in as deep as I could and pumped my seed deep into my Aunt’s womb. At only 12, I didn’t know enough about the risk of pregnancy so I innocently and happily filled Aunt Ellen with my semen. Slowly, I let my cock soften a bit then I carefully slid it out of her and went back to my room.
The next morning, it was the same thing — a normal breakfast and no mention of the previous night. I spent the third day of her visit eagerly anticipating her last night with us. After bedtime, it was business as usual. At about 1 a.m. I could wait no longer and I crept into bed with Aunt Ellen. Again, I found her completely nude. But this time she was sleeping face down with her knees pulled up underneath her and her ass sticking up under the covers. Odd sleeping position, I thought, but perfect for giving me easy access to her big warm pussy. With her in this position, instead of laying down beside her I carefull pulled the blanket and sheet up over her back, exposing her ripe ass. Then, I got into position on my knees behind her. Just as I was about to slide my cock into her pussy opening, I had another thought. In the dim moonlight, for the first time I could actually see her round ass and gaping cunthole. I moved my face closer to get a good view. I could smell her pussy juices and see her cuntlips glistening. Some boys at school had once told me that guys like to lick women’s pussies, so I decided to give it a try. Cautiously, I tongued her pussy lips then pushed my tongue inside of her. At first it tasted strange and new, but after a while my saliva mixed with her juices as I gently sucked at her cunt. As I buried my face in her big, sloppy cunt I could smell her asshole near my nose. I found the smell of her ass very erotic, and so I moved up and tongued her asshole. After I had satisfied my appetite for pussy and ass, I got up on my knees again and positioned my bulging cock between her butt cheeks. The entire area was soaked and slippery from my licking and sucking, so I slid my cock up and down her crack a couple of times then pushed forward. As I felt it enter my Aunt, the feeling was a bit different — somewhat tighter and not quite as soft. I surmised that the difference in feeling must be due to the different position Aunt Ellen was in this time. It felt fantastic anyway, so I pushed in deeper. As I gradually slid my entire cock in, I heard Aunt Ellen let out a low, soft moan. I stopped as my balls pressed against her mound, terrified that she might wake up. After a few moments of silence, I was sure she was still sleeping. As I cupped her ass cheeks with my hands and started to pull out a bit, I discovered why she felt different this time. I wasn’t in Aunt Ellen’s pussy at all — my cock was buried deep in her asshole! With all the slippery wetness, this new position, and my lack of experience, I had accidentally pushed my cock into her asshole. It was much tighter than her cunt and just as much fun to fuck, I thought. In my young mind, I worried that maybe boys weren’t supposed to stick their dicks in a girl’s (or in this case a mature woman’s) ass. But the feeling of my Aunt’s tight ass gripping my cock as I pushed in and out of her soon made me forget those worries. I became completely lost in the moment, seeing her round ass cheeks bobbling in front of me as I pushed into her. Soon I forgot all caution and began slamming my Aunt’s asshole, watching her body lurch forward and jiggle with each thrust. With a few last thrusts, I held my cock deep in her and shot stream after stream of cum deep into Aunt Ellen’s bowels. As I finished spurting, I held onto her ass to steady myself while I caught my breath. After several minutes of remaining still, my cock was still rock hard and buried to the hilt in my Aunt’s ass. Her ass was gripping the base of my cock tightly, preventing it from going soft. While I was contemplating what to do about this, I felt my Aunt’s ass flex and squeeze my cock even more several times in a row. This got me eager for another round. Throwing caution to the wind, I began to move in and out of her ass again. With her bowels full of my cum, her asshole was much more slippery than before and I pumped in and out of her very easily. As I fucked my Aunt’s ass, suddenly she raised up on her hands, spread her legs more and arched her back. Shocked and surprised, I knew she had to be awake. I stopped suddenly and started to pull out. But before I could, she pushed back towards me and engulfed my cock with her asshole. As I remained motionless, my Aunt Ellen was assfucking my cock! In disbelief, I watched my 41 year old Aunt knowingly and eagerly slam her ass back into my engorged cock. Soon, this was too much to take and somehow she could tell I was ready to cum. Before I knew it, she pulled away from me, swung around quickly, and took my cock in her mouth. As my cockhead pushed through her lips I was already starting to shoot. Most of my cum went down my Aunt’s throat and the rest dribbled out of her mouth, down her chin, and onto her big pillowy tits. She sucked the last few drops out of my softening cock, then scooped the cum off her chin and tits, put it in her mouth and swallowed. I fell onto the bed, totally and completed in bliss while my Aunt Ellen rolled over and put the covers back over her. After a few moments, I wasn’t sure what to do so I crept out of the bed and returned to my room.
The next day my Aunt Ellen left after my parents returned. She gave me a knowing smile as she got into her car. I saw her several times after that, but we never discussed those nights. Also, I never had any more sexual contact with her until almost 20 years later. But that’s another story….
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A young man’s first time with an unusual lover.
How far would you go for the one you love?
This work is purely fiction and has no links to any real life characters or events. All characters in this story are 18 and over. All work is of my own writing. It’s a work in progress. Story is not based on any real life people. All incidents are purely fictional. Any resemblance to real person, living or dead or real life events is purely coincidental.
Out of town on business and miles from the wife can tempt a man to stray.
I had no idea where the address was. I decided I had to take a cab, and had the money, from sucking cock. I was not sure what to expect, likely some sleazy hotel, but I found myself in Manhattan. Perhaps I should not be surprised, these kind of people had all the money, and thought they could afford anything they wanted. I found myself deposited at one of the most posh buildings I had ever seen, and seeing a doorman, I looked at the sheet of paper. I needed to know the name, I knew the man would stop me from going in, besides I didn’t know the apartment number.
The man looked me up and down. I knew he was aware what I was, or at least had guessed by now. He seemed prepared, and took me to the elevator, and escorted me himself. I was surprised when he took me up to the top floor, where I knew some of the most expensive penthouses in the city had to be. He knocked on the door, as I stood there nervous, unsure of what to expect.
I was shocked when a woman answered the door, certain it must be a mistake. The man smiled. “I believe this is your guest you were expecting.” The woman who had to be in her forties and a good fifty pounds overweight smiled. “Of course John, thank you.” When the man was gone, the woman turned to me. “Well come in dear and make yourself comfortable.”
I went into the huge living room, with massive windows, with views of the city. I felt the woman’s hands go in front of me, and start to undo my jacket, and it slipped to the floor. The woman motioned her over. “Come, what can I get you to drink? Wine?” I shook my head. “I am only 17.” The woman chuckled and poured her a glass of some kind of alcohol, not wine. “Don’t worry, it is just between us. We have been told this is your first time, you may need a little courage.” She took the glass and nearly choked on the drink. “What is it?” A man had walked into the room, a tall but quite thick around the waist man, who looked to be at least a decades older than the woman. “My best 100 year old Scotch.” He came over and accepted his own glass but his hands went to my breast and squeezed tightly. “He wasn’t lying, look at the breasts on her honey.” His wife took my other breasts and rubbed my nipple. “I know why we always go to him, he knows how much of a breast woman I am.”
The woman continued on my breasts, as her husband went behind me, and undid my corset, letting it fall to the floor. His wife kneading my breasts harder as she whispered. “Your name my love?” I finally found my voice. “Rose.” Her husband had slid his hands down and removed her garter and slid his hands into her thong. “Is that a nickname for your lovely rose lips?” I shook my head. “No.” His wife laughed. “I am Jen and my husband is Mark.” Feeling the thong pushed off, and my stockings, down to the floor, my face went rose red, aware I stood naked in front of not one but two people. I know I had done so with John, she laughed her pimp’s name seemed fitting, as that was what the man was, but this was different. I wasn’t only a virgin, but straight, I had never been touched by a woman before.
Jen noticed I still looked extremely uncomfortable as her husband lifted my legs one at a time, to remove the last remnants. “Oh the little lamb is scared Mark. I think we need to give her another drink.” Mark stood and went to pour more, as Jen pulled her down on the couch. Mark sat down with her and handed her a much fuller glass. I shook my head. “I am seventeen.” He pressed the glass into my hand and Jen whispered. “Trust me, it will make it easier for your first time. Now drink up.” I slowly sipped the glass, still burning as before, my head already spinning from the first glass I had drunk. My body felt warm, and I had to rest my head back against the couch.
Jen smiled as her hand went to my right breast. “See, doesn’t that feel better?” Mark’s hand went to my other. “We will soon make you feel so good.” I felt the hands on my breasts, rubbing at my nipples, light at first, but with more and more pressure. As Jen bent and started suckling on my breast as if she was a baby breast feeding, my head went back against the cushions. I kept trying to tell myself, in the fog of my brain, this was wrong, and I wasn’t gay, but my body was going so wet. John noticed, and putting his hand between my legs, felt the juices. He smiled at his wife. “She is definitely nearing ready for a cock inside of her. Should we toss a coin, see who goes first, I know you have that new dildo you are anxious to try out?” I heard the words and shook my head in the fog. “No, please no.”
Jen reached for another glass and put it to my lips. “Drink beautiful, drink.” I found my lips pressed open, as more of the whisky went down my throat, forced to swallow or drown. Mark smiled. “I think she is right, it is her first time, she should have a real cock between her legs..” Jen was pouting but agreed. “But I get to enjoy that fine cunt first.” I had no idea what was happening, my mind all a haze, not sure what she meant. My body betrayed me as I whimpered when Jen’s hands left my breasts. Her husband laughed and kissed me. “Oh don’t worry, I’m here.”
At first as his mouth played on my breasts, I didn’t notice Jen. She disappeared from my side, but I barely registered as my legs were put on the coffee table, as if for a doctor’s exam. I jerked, even in the haze, when I felt a hand down there. Jen ignored me, and parting my lips, she stuck her mouth down there, her tongue dipping inside of me. I whimpered and sobbed, feeling the tongue licking at me, increasing as the tongue began dipping inside of me over and over, a hand massaging my clit as her mouth worked. Her husband’s mouth continued on my breasts. I found my hand placed on a cock, realizing somewhere along the way, I wasn’t the only one who stripped, both seemed to be. When my hand remained still, Mark forced my hand up and down his cock, keeping a hold, until I had the motion myself. I had little sense of what I was doing, as I pumped him, feeling the cock go hard in my hands. As I was starting to come to my first orgasm, He removed his mouth from my breasts, and I found my head forced down over his throbbing cock. I opened my mouth, as the cock was fed into my mouth, he pumping it himself, as he climaxed hard, at the same time as I did. Jen was smiling as she licked me clean, and I was forced to lick Mark.
I found myself half carried into the bedroom and laid down on the bed, in the middle, but pillows under my head. Jen lay with me, her mouth back to my breasts, as I felt Mark between my legs. He saw my eyes as I noticed he was still hard. He smiled and motioned to a bottle on the table. “When I knew we would have you all night, I popped a nice blue pill.” I squirmed as a finger inserted deep into me, and another, and another. Jen soothed me. “He is just stretching you, wouldn’t want to cause you too much pain your first time.” Mark heard me continue to sob and motioned to his wife. “Perhaps you should give her something else to think of.”
I was worried it was more booze or some kind of pills, my head already in a total fog, but no. I barely registered what she was doing, as she put a knee on either side of my head, until she lowered herself over my mouth. She smiled. “It is my turn, eat me out my pretty Rose.” I wanted to protest, to fight, but my arms were lethargic. I found the pussy down over my mouth, and when I protested, the pussy pushed forward, cutting off my nostrils, making it near impossible to breath. I finally started to lick, having no idea what to do, but desperate to breath. I was so lost in it, I barely noticed when my legs were being lifted until they were bent so they were nearly up to my shoulders, and my ass up in the air. Even with his stretching, and how wet I was, the pain was intense as I felt the head of his cock pushing in.
He smiled as he fed the start of his nine inch cock into me. “I am going to do it quick, it will hurt at first, but I am sure you will soon enjoy.” With that he rammed hard into me, ripping through my hymen, in one swift thrust. Even with all the booze, the pain was intense, and I bucked even in the position. I was unable to push him free, and as he held in place to give me time to adjust, the burning was intense. He slowly started to fuck me with fast deep thrusts, and every time I thought I may get used to the pace, he sped up, fucking me so hard my head bounced. But still the pussy remained over my mouth, and I was forced to continue to lick. Jen cummed hard in my mouth, as I felt her husband fill me. I was grateful, due to periods, I had been on the pill for years.
I felt my legs drop, and Jen bent and kissed me. “Good girl. Now up on your knees pretty one.” I was so dizzy and in so much pain I wasn’t sure I could, and collapsed when I tried, on my front. Mark shook his head and thrust a pillow under me, so raise my ass up. “She seems a bit of a feather weight, but this should allow you room.” Jen had gone into her bed side table, and pulled out a huge strap on, and got behind me. “I have been waiting to try this out.” I was nice and stretched from him, but it was still intense, as the huge dildo forced its way in. I was soon taking another cock, as her husband’s slipped between my lips, as I was forced to once again suck him off. By the time they had both cummed again, and I had, the whole world was so hazy. I found another glass at my lips and this time I didn’t protest as I drank, and all real consciousness slipped away, as if I was removed from my body. Jen kissed her husband. “I’ll get the lube.”
In the morning I woke up with a painful groan. My head was throbbing desperately, but so was the rest of my body. It took a few moments, and noticing the two naked bodies I was pinned between, to remember. I thought them asleep, until Jen who was in front of me, began massaging my breasts and took me in for a kiss, and I could feel Mark position me for a fuck. After all the use the night before I was loose, but dry, and no booze to mask it this time. My protests and cries were cut off by a hungry kiss, my lips forced open, as a tongue slid inside. Thankfully he came quickly, and no more blue pill, he went for one ride.
Mark pulled me out of bed. “Take a shower, you will find clothes in the bathroom.” Jen pulled me in. “I think we will share the shower.” Mark left them to it, and I found myself in a pulsing hot shower, having my body scrubbed clean from top to bottom. I was forced to finger her, as Jen fingered me, and we both climaxed at the same time. I was relieved when I was let out of the shower and dress. She handed me pills and explained when I protested. “Something for the headache. You drank a lot last night, and we used you for hours.” I winced as I felt a hand on my ass, as I took the pills, hoping they’d work soon. “Stop.” She laughed. “Oh, I had a feeling you might forget that part.”
Back in the sitting room, I refused to think of what I missed. Mark handed me an envelope. “John has been paid his share already, here is your money.” Jen slipped some money in her bra. “And here is a tip. You can keep the clothes.” She was grateful to have real clothes to leave in. “Thanks.” Mark French kissed her. “Our driver will take you home. We’ll be seeing you soon.”
I rushed away as soon as I could, finding a car waiting for me downstairs. I got back to my apartment building, where John was waiting for me. He had a Cheshire cat smile. “I heard you were quite the ride. I am sure you never made 200 in one night.” I pulled back. “200? That is all I made for an entire night?” He laughed. “After my share of course. A discount to get them to come back. They have hired you again, once a week for the next year.” I cringed at the thought. “I need to sleep.” He handed me a phone. “You will get a text when your next client is ready, day or night.” I took the phone. “Fine. But no more women.” He pulled me in tight. “If you tell me what you will do again, I will hire you out only to women, and perhaps some canines.” I pushed away. “No. You can’t expect me to take a dog.” He laughed. “Soon enough. The rich have odd tastes.” I pulled away from him, and hurried away, tears streaming at the memory, and thought of a dog.
He took out his own wad and laughed to himself as he counted the three grand. “The little slut really thinks I got paid so little for her cherry.”
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