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When my ex-wife Deanna and I had first gotten married, her younger sister Jillian was about 18 years old. I had known her since she was around 15 or 16. It was pretty obvious she had a bit of a crush on me. I was 23 at the time, so I guess she must have thought I was a cute older guy. The thought of flashing her didn't enter my mind because of her age and the fact that she was my girlfriend's (later my wife's sister).
My wife's mother had died when both girls were quite young and my wife moreor less became a mother figure to her. So after we got married, it was not unusual for her sister to visit our apartment quite often. My interest in flashing her started when I discovered that she was trying to get a peek at me. On several occasions I became aware of her in the vicinity of the bedroom or bathroom door at times one might expect me to be nude or getting dressed. I was very hesitant to do anything too obvious to outright flash her because I was not sure what would happen if it backfired and my wife should find out. But it was tempting as by this time she was a full-fledged teenager who apparently had a fairly healthy sexual curiosity. My wife used to tell me about some of the questions her sister used to ask about boys and sex. From what I could surmise, I felt certain that Jillian was definitely a virgin, and most likely very limited in her sexual experience.
I began to wonder if there might not be some way to flash her safely. An opportunity came shortly after her 19th birthday. My wife and I had planned to take a week's vacation to Disney World as it had only recently opened and we were curious about what attractions were there. My wife suggested that as a graduation gift to her sister, we could invite her along on the trip. We were not exactly making the greatest income in the world, so I knew we weren't talking about getting a separate room for her which meant, of course, that we would all be sharing the same room. This could lead to some interesting possibilities, I thought.
We decided to drive down to Florida where we would stay at a Kissimmie area hotel for which we had reservations. But before we arrived there, the first test of the plan came when we stayed overnight on the road at an economy motel. It had been a long day of driving and everyone was tired so we all pretty much were prepared to go to bed early. I staked out the bed to the left, being sure to grab the side of the bed next to the nightstand that separated our bed from the one my sister-in-law would be sleeping in. As the ladies shared the bathroom to get ready for bed, I removed all my clothes except for my jockey shorts and climbed into "my side" of the bed. When everyone was in bed, I waited as everyone drifted off to sleep. My wife is a fairly heavy sleeper, so it wasn't long before I could quietly remove my shorts for any fun that might follow. There was just enough light in the room from a small gap in the curtains that with the light out in the room, you could still make out distinctly features of my sister-in-law in her bed. She was dressed in a medium length nightie and was covered up, but I could see enough of her to tell which way she was facing and could see enough ofher face to distinguish her eyes, nose, etc. When I was sure my wife was asleep, I stroked myself slowly under the covers until I was hard, then quietly pulled back the covers to reveal my cock should my sister-in-law wake up and roll over to face our bed. But being as tired as I was from the first leg of the trip, I fell asleep.
During the night, I - being a lighter sleeper than my wife - became aware of her sister getting out of bed, I supposed that she was heading to the bathroom. Though I was uncovered, I was no longer erect but there wasn't much I could do about it now. Little sister stumbled her way to the toilet, turned on the light, and closed the door. This gave me the chance to stroke myself a little in case she came out and happened to glance toward our bed.
As she flushed the toilet, I stopped stroking my now semi-erect cock and placed my arm over my face in such a way that it would be hard for her to see if my eyes were open and yet allow me to peek out at her. When she came out of the bathroom, she did not immediately turn off the bathroom light, but instead wandered over to one of her suitcases to get something out of it. With my eyes open underneath my forearm I could catch a glimpse of her as she kneeled down to open her suitcase. The latch of her suitcase made noise as she opened it, and I guess she looked over to see if the sound had woken us up. In doing so, she got a great view of my fairly well-lit and rapidly hardening dick. It was extremely difficult to control my breathing at this point as the excitement of knowing she was looking at my dick was really affecting me. Her eyes opened wide as she realized she was staring at my dick just standing there at a rakish angle from my belly. She started to look through her suitcase for whatever it was she wanted and back again at my dick several times over the next minute or so. It was clear that I had her attention and that she was indeed interested in what she was seeing. I considered reaching down and touching or scratching myself, but I was afraid that would give the little game away. She eventually found what she was looking for (Chapstick, I think), returned to the bathroom and came out again. She stood there for a minute, obviously still taking in the sight of my erection before turning out the light and climbing back into bed.
When she reached the bed, she was now out of my eyesight since my arm was blocking my sightline to her face, but I could tell she did not lay down immediately, and was probably sitting on the edge of her bed to get a closer look at my cock. Though the room was darker now, I could tell from glancing down at myself that there was still enough light to reveal my cock to her. After a few minutes, she did lay down and pulled the covers over her. Even though it was exciting to know that she could still see me if she was facing in my direction, I could not maintain a full erection much longer and I could feel my hard-on start to droop a little. I figured that was enough for the night, I needed my sleep, so I just rolled over as if still asleep, and laid on my stomach for awhile. I could tell that she was starting to go back to sleep, and as soon as I was sure she was fully asleep, I pulled the covers over me and carefully found my shorts near my feet and put them back on. As usual, my wife who could sleep through anything had not stirred the entire time. I wondered how the rest of the week was going to go with this room sharing arrangement, and finally drifted off to sleep myself.
We all woke up the next morning to prepare for the second half of the trip down to Florida. My wife's sister never said a word about last night, and I got no indication that she mentioned it to my wife. But was she ever affectionate during the day, giving me little unsolicited hugs throughout the day. I asked: "What's up with you today?" She replied, "Don't you know you are my favorite brother-in-law?" I thought to myself, God this is nice but I hope I haven't opened up a can of worms I can't close again.
We got quite a surprise when we arrived at the hotel we had booked. Bear in mind that this was shortly after DisneyWorld first opened, and the Orlando-Kissimmee area was nowhere near as developed as it is today nor was Disney World the giant monster it has since become. Hotel and motel rooms were at a premium. When we arrived to register, the clerk told us that there had been a problem with our reservation and that the double room we had wanted was not available, but he would be glad to upgrade our room. There were only a few rooms left, but we could have one if we didn't mind a room with just a single king-sized bed. Immediately, I knew this could prove interesting. I looked to my wife and her sister to see if that would be alright with them. My wife seemed a little uncomfortable with the idea, but I told her our chances of getting an available room at another hotel might not be possible. I looked at my sister-in-law and she was looking down at her feet, sort of shyly, with only the slightest smile on her face. We decided that we didn't have much choice so we took the room.
God, the possibilities were running through my mind. There were bound to be some risks with this, but who know's what might happen with the three of us sharing one bed. The first two nights were somewhat disappointing because my wife had staked out the middle of the bed thereby separating myself and her sister. I guess she thought it might be more proper that way. The only thing I tried during the first two nights was an early morning (when the room was getting a little brighter) nude romp to the bathroom with a raging morning erection.
In doing this I had to go around past the other side of the bed to get to the bathroom. I had no idea if my sister-in-law was awake at this point, but if she was she certainly would've gotten a good show of my erect dick bouncing up and down as I passed by. It took a little while to get the stream going once I was in the bathroom since I was still hard. I finally took a leak, and then realized that if I flushed the toilet it might wake her up, but also my wife so I left it unflushed. My cock was still a little more than semi-erect on the trip back to bed. I tried to sneak a peek at Jillian's eyes, but she appeared to be asleep.
On the third night, I knew I had to do something to alter the sleeping arrangement. When we got back to the hotel about mid-evening, the girls wanted to take a dip in the hotel pool before it closed for the night. My wife asked if I wanted to come along, but I declined saying I was tired and I might go to bed early. They got ready to go to the pool. This was the first time I had seen my sister-in-law in a bathing suit since we'd met. She stood about 5 and a half feet tall with long brown hair, somewhat flat-chested, but the one-piece bathing suit she wore really accented her vaginal area and pronounced mound. I took a couple of quick peeks at her crotch and undressed her with my eyes. God, did that ever make me hornier than I was already was. The girls left, and I climbed into bed making sure place myself in the middle. I took a chance and removed my underwear before I got in bed, so there I was: stark naked under the covers. I only hoped my wife wouldn't notice this when she climbed into bed because it might arouse suspicion. Though I normally sleep in the nude, she might think it funny to do so while in bed with her sister next to me. So I placed myself as far down as possible under the covers thinking that if she did pull the covers back when she got into bed she would only see my bare back.
They came back about 45 minutes later. I pretended to be deep asleep, so they were a little quiet as they prepared for bed. Jillian whispered she was going to take a shower tonight instead of tomorrow morning, so she headed for the bathroom. I could hear my wife getting out of her clothes and into her nightie. She soon climbed into bed, turning the light off on her side. She must not have noticed I was naked as she got into bed, and I could tell by her breathing that it wouldn't be long before she'd be fast asleep.
Jillian was still in the shower and the light on her side of the bed was still on. At this point, I am really getting excited at the possibility that she would soon get into bed next to her nude brother-in-law. I had been laying on my stomach, but as I waited for her to come to bed, I quietly rolled over on my back, my dick already getting hard from thinking about her getting a look at my erection a few nights ago.When she came out of the bathroom, I kept my eyes closed and tried to control my breathing to make it seem as though I was still asleep. She moved about the room, went into her suitcase once or twice, and then I could sense her approaching the bed. She pulled back the covers on her side and in doing so, exposed the head of my hard-on. It was becoming harder to breathe properly and keep my chest from heaving at this point as I was sure she could definitely see my dickhead poking out from under the covers. When she pulled back the covers to that point I expected her to get into bed fairly soon, but she only sat down on the bed and sat still. She must be looking, I thought. I was right, because slowly I felt the covers being pulled back even more to expose my entire cock. I thought I was going to go crazy; my heart was pounding knowing that she was getting a very close look at my hard dick. She pulled the covers back even more to expose my balls. She must have looked for a minute or two when my wife began to stir, and then I felt Jillian pull the covers back over me. Yes! She was trying to peek at brother-in-law without Deanna finding out!
She then turned out the light and got into bed. I began to wonder if she had plans to get a little feel of my dick during the night, but that was not to be. However, I did think I could detect a little movement under the covers on her side and noticed a little change in her breathing. Maybe it was wishful thinking on my part, but I wondered if maybe she might be masturbating right next to me. Maybe, maybe not. But just the thought of it was making me even harder than before. Later, it seemed as though she was sleeping. I rolled over toward her with my dick pointing straight at her ass. If she moved back toward me, she might feel my cock against her ass. This was not to be either, but it was fun imagining it happening. I waited for it to happen for awhile, but eventually fell asleep.
The next morning, my wife got up first to take a shower. This gave me time to get my underwear on before she got out of the shower. That day we decided to head over to the East Coast to check out the beaches. Keep in mind that we had pretty much seen it all at Disney because at that time there was only the Magic Kingdom and those were the days of ticket books for the rides. They didn't do unlimited rides or build the other theme parks until later.
The experience the night before had made me extremely horny, and I had not had the chance to properly jerk off. I was thinking that maybe tonight I would take a chance and jerk off right between the two of them. We spent the day at Daytona Beach, and returned to the hotel late in the evening. Jillian was tired, so she wanted to go to bed early. My wife, on the other hand, was wide awake and suggested we go to the hotel lounge for a couple of drinks. I agreed, and off we went.
` While we were drinking, we got to talking about the vacation and the fun we were having. She confessed that the only thing that could make it perfect would be if we could make love, but that wasn't possible with her sister sharing the bed. I told her that I wished we could too, and that I was really getting horny. Then she floored me with her next statement. She said: "Maybe we can't make love like we want to, but if we're quiet, I could get you off." Whoa! This could be interesting, I thought. I played along with the idea. I asked her: "Do you think we could get away with it?"
So when we got back to the hotel, Jillian was already asleep. We quietly undressed, and got into bed: me first. I was surprised that my wife didn't react to my climbing into bed next to her sister while I was nude, but I guess the drinks had gone to her head. We began to kiss and fondle each other. I decided that whatever was going to happen, I wanted to let Jillian in on it, at least as a spectator. As my wife and I were making out, I stretched my leg back toward her sister. Every now and then, I would nudge her with my foot to try to stir her. She was sleeping on her stomach with her face turned away from us. The first few nudges didn't have any effect, but then I nudged a little harder, and I knew I had woken her up by a slight body movement on her part. Right away, I whispered (not too quietly) to my wife :"Do you think she's asleep?" My wife whispered back: "Uh-huh", then added, "Lay back. Let me stroke your dick." I was sure our whispering was loud enough for Jillian to hear, and if she was awake as I was sure she was, she would now know that we were fooling around, right next to her.
I laid on my back as my wife began stroking my hard cock. I knew it wouldn't take long to come since I had been so horny. But I tried to prolong this experience as long as possible. Just in case Deanna was asleep, I nudged her again with my foot hoping she would think it was accidental. I detected a change in her breathing and was positive she was awake and listening. My wife continued rubbing the length of my cock, but only the head of my cock was visible from under the covers as she did so. The rustling of the sheets and my occasional horny sighs must have been heard by Jillian.
I was getting closer to coming, and my wife sensed it. She whispered in my ear, "Let's not get the sheet wet. Come in my mouth." At that, her head made it's way down to my cock, and she began to finish me off with her mouth. She was making enough of a slurping sucking sound that I knew Jillian could hear it. Out of the corner of my eye, I could see Deanna slowly and quietly turn her face toward us. I wanted to hold back to let her see the show my wife was unintentionally putting on. Jillian was being very careful not to move her head too quickly, but she soon had her head in a position to get a view of the action. Then I let go. I tried not to be too obvious, but made just enough noise to signal her that I was coming in her big sister's mouth. I couldn't see her eyes, but I knew she was watching either my reaction to the blow job or watching her sister's head bobbing up and down as she sucked me dry.
Afterwards. my wife snuggled next to me and I held her as we both fell asleep, though it took me a little while to get to sleep with the excitement of having Jillian watching me come.
Early the next morning, I heard Jillian get out of bed and head for the bathroom. I peeked out of one eye, and what did I see? Jillian had been sleeping next to me the whole night...in the nude. God, she had a beautiful little ass. Now, it suddenly occurred to me that she must have decided to "return the favor" and give me a peek at her. Or maybe she had bigger plans. I don't know.
We decided to stay in the area for another day which was fine by me. I was in no rush to return home at this point. The sight of watching my cute sister-in-law climb out of bed totally nude made me want to stick around to see how this played out. I couldn't believe I had slept next to her all night, both of us nude, and nothing had gone on between us. Surely she must have intentionally given me a chance to look at her or touch her, but I was just a little too concerned about her reaction if she didn't appreciate my advances. But now, knowing that she had been nude all night made me decide to pluck up the courage to see what might happen if we had another night in the same bed.
We had another busy tiring day swimming and sailing and by the time we got back to the hotel, we were all pretty tired. My wife and Jillian both decided they were going to go to bed early. I felt the need to head to the jacuzzi room and relax a little while before turning in.
When I came back to the room, all the lights were out and it was difficult to see anything in the room at first. I could barely see the bed, but I could tell both women were asleep by the sound of their breathing. Standing by the foot of the bed, I started to undress quietly. As I did, my eyes began adjusting to the darkness. I looked at the bed and realized I had screwed up any plans for checking my sister-in-law out tonight. There was a space in the bed for me, right where my wife usually slept. She had apparently rolled over toward the middle of the bed as she was sleeping.
Damn, I thought to myself. I blew it. Oh, well, so much for that idea. I finished undressing and climbed into bed in the space usually occupied by my wife. Since there would be no action tonight, I fell asleep.
Sometime, in the middle of the night, I became aware of my wife's hand on my cock. I don't know how long she had been playing with it, but the stimulation must have woken me up. I found myself with a rapidly rising hard-on as she began to stroke it ever so slowly. Her grip on my cock was a little tighter than usual, but the agonizingly slow tempo of her strokes were driving me crazy. I looked down at her as she pulled the covers back to expose my engorged cock, and she rested her head on top of my chest as she inspected my member as she stroked. I lifted my head to check on Jillian to see if she was asleep. Jillian had her back turned towards us as she slept soundly on her side.
I had to content myself with the idea that I was only going to get a handjob. Maybe my wife would give me a repeat performance and suck me off again. I just laid back and let her continue with those long slow strokes again. The slow pace of her hand rubbing up and down my shaft was teasing me. It felt incredibly good, but not quite enough to bring me to orgasm. I just laid back and enjoyed the maddening sensations as her fingers ran up and down the length of my cock.
Suddenly, my wife raised her head and put her lips close to my ear. For a few minutes, her warm breath in my ear was getting me more an more excited. Then I heard her say, "Let's not get the sheet wet. Come in my mouth." The words sounded familiar, but the voice was not my wife's; it was her sister's voice! Somehow, and for some reason, they had switched places while I was down in the jacuzzi. It was my wife who was sleeping soundly on the other side of the bed. And Jillian was the one who was now making her way down my body to my cock. The sudden realization of what was happening - and what was about to happen - gave me a head rush I had never experienced before. Part of me was excited knowing that my sweet sister-in-law was about to put her mouth on my cock.
Another part of me was well aware of the element of danger; though my wife was a deep, sound sleeper, she could wake up at any moment and catch me with my dick in her sister's mouth. My heart started to palpitate and my breathing became labored. This totally dangerous situation coupled with the sensations I was about the feel on my cock made me more excited than I had ever been before in my life.
Jillian worked her way slowly and steadily down the bed, only stopping occasionally to plant a kiss here and there on my body. Instead of facing away from me, she positioned herself between my legs so she could face me. There was just enough light in the room for us to see each other's faces and make eye contact. Looking me straight in the eye, she took my cock in her hand and resumed the stroking she had begun earlier. The entire time she rubbed the length of my dick, she continued looking me square in the eye. She was not wearing a smile on her face, but a lustful, sultry, soulful stare was there instead. She looked so damned sexy. There she was, lying between my legs, giving me THAT look. I could see that she was completely nude. I could see her ass near the edge of the bed with her legs out over the foot of the bed. One leg was stretched straight out, the other was bent at the knee, slowly moving up and down.
She continued torturing me with those excruciatingly slow, dick-length strokes, up...and down...up...and down...up...and down. The entire time, her eyes never left mine. For minutes she kept that snail-like pace going on my cock. I wanted to scream, I wanted her to go faster, and it was driving me mad that I could do or say nothing to urge her on. Up...and down...up...and down...up...
Then, she began to increase my suffering. Each time she was on the downstroke, she pulled my cock towards her lips and planted a little, tiny kiss on the head. This went on for quite awhile. I was out of my mind from the excitement. Her teasing of my cock as well as the knowledge that my wife might wake up at any moment was causing adrenaline to surge throughout my body. My heart was racing. And still, Jillian looked me right in the eye.
Her little kisses became little licks. Her darting tongue now snaked out on the downstroke, touching the underside of the head of my cock. Those little licks turned into swirling licks all over and around the head. I didn't know how much more of this I could stand. Each time her tongue made a circle around the tip of my dick, she would spit out a bit of saliva. At first, she coated the head of my cock with her spit, but in a few minutes, my entire cock was slobbery. And still she continued her slow strokes and licks. Her eyes remained glued to mine.
I was almost out of head by this point. I wanted to grab that gorgeous little body, turn her over on the bed, and penetrate her virgin hole with my erect member. I wanted to make her scream the way I felt like screaming. I wanted to look her in the eye the way she was piercing me with hers. I wanted to fuck her like I had never fucked a woman before.
But there was no way I could with my wife sleeping right next to us in the same bed. I clutched the sheet below me with my hands, somehow hoping if I could get a grip on the sheet, I could get a grip on my reactions to this most wonderfully, unbelievable blowjob I was receiving from Jillian.
Without warning, her mouth took hold of my cock and I suddenly found myself engulfed in the warmth and wetness that awaited inside. I gasped. I had no control over my reaction to her sudden oral attack on my dick. Quickly glancing at my wife, I could see that she was still asleep, and just as I was looking her way, Jillian had lifted her head and down again it came, taking in about a third of my cock's erect length. Jesus, I thought, if she's a virgin then she must have the best natural instincts of any woman or girl I'd ever been with. As good as my wife was at giving head, her Jillian was even better. Once more, as I now looked directly at her, she plunged her head down on my cock, taking in about half the length into her stretched mouth.
Her lips grasped my dick directly beneath the head. Instead of bobbing her head up and down, she began to use her lips on my dick much like a person sucks on a straw. Her lower lip began to massage the underside of the head of my dick while her tongue swirled around the head itself. This was even more unbearable than those slow, strong strokes of her hand. I had no real concept of time at this point, but she must have continued her lip action for a half-hour. I came close to cumming at least a dozen times, but each time she seemed to sense I was nearing orgasm and slowed down to an almost complete stop. Everytime she did that, I wanted to grab her head, force it up and down on my cock and fuck her mouth like it was a cunt. I was totally under her spell at this point. I could do or say nothing, I could make no noise. She was in control, and she knew it. Not once did she take her eyes off mine as she continued to use her mouth, lips and tongue to take me to heights I had never known before. I was lost in sexual heaven.
Her pace picked up. Now she began to bob her head, slowly at first, then faster. Up and down, up and down, up and down. Faster, and then still faster. She was determined to bring this blowjob to a close with a big finish. I grabbed the pillow from beneath my head, and shoved it in my mouth, clenching it with my teeth, hoping that any noise I might make would be muffled. And amazingly, she kept here eyes on me every second as she took me closer and closer to orgasm.
Then, I came.
Every man and woman who has ever had an orgasm knows there is no sensation more strong, more powerful and more wonderful than the one you feel the exact second you reach orgasm. For me, this was the mother of all orgasms. I felt as though all the pent-up cum I felt rising from my balls had consolidated and as I came, the release of all my semen shot out of the end of my cock with a force and velocity I had never known. Had my dick not been in Jillian's mouth, I can honestly say -without exaggeration - it would have hit the ceiling. I could almost feel the force of my orgasm push my ass back into the mattress. I cannot imagine what it must have been like for Jillian to be the recipient of that blast.
But I did have a clue. I looked at her eyes as that first tremendous blast lefmy cock and headed for the back of her throat. She must very well have been virgin of the mouth as it was obvious she was not prepared for that first shot ofsemen. The moment I let go in her mouth, her eyes bugged out and her cheeks puffed up. She pulled her mouth away from my dick, struggled for breath for a few seconds. While she caught her breath, my cock was like a high pressure fire hose out of control. I continued cumming: on her, on me, and on the bed. She quickly shoved my dick back in her mouth and finished me off. When I had finished unloading my cum, she kept my cock in her mouth and resumed that slow sucking action she had begun earlier. She kept looking at me, only this time her eyes were opened wide as if to say, Jesus!
She kept on sucking gently until my dick returned to its flaccid state. She finished by giving the head of my cock a little kiss, then she moved up the bed, covered us up with the sheet and blanket, and gave me a big hug. She raised her head up to mine to give me a kiss. I could taste the saltiness of my own come in her mouth as her tongue reached into my mouth to brush against my tongue. Then she whispered in my ear, "You owe me."
And with that, she rolled over and went to sleep.
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Posted by ATCFNM at 3:18 PM