When I was 19, we went on a regular yearly vacation with various family members to a resort in the mountains of some state which will remain nameless. This included 3 cousins of mine, all sisters, two 20 year old twins (Lisa and Marie) and an 18 year old named Sally. We'd spent time every month or so together, so we knew each other fairly well. They were all amazingly hot - blond, tall, all volleyball players, etc, but as I said, also my cousins. The family was generally cramped in the resort, so all 4 of us younger people were put into a room of the lodge together. The room had a small bed in the corner of the room (twin probably, though it's hard to remember), and a couch plus a king sized bed on the other side of the room across from each other. I slept on the small bed being the only male, the twins shared the king bed, and the 18 year old (Sally) was on the couch.
As with previous years, we entertained ourselves at night by playing various games while the parents were drinking and playing poker in the main room. This year we played both innocent games (card games, video games, board games, etc), and slightly less innocent. Somehow one of the girls had suggested a game of strip poker. It was exciting for the first few minutes, as I considered the idea of seeing one of my cousins naked. However, once it became Lisa's turn to lose her shirt, she'd backed out. I was too conscious of the fact she was my cousin to press the matter.
We also continued a game we had invented where you screw with people while they're sleeping. In past years this had been things like peanut butter on their fingers, warm water on their hands to make them pee (never did work), ice cubes tossed under your blanket, etc. It was a given if you fell asleep first, you were likely to wake up at least once due to people playing tricks on you.
On the 4th or 5th night, after playing a couple card games and watching TV, everyone went to sleep. I was wide awake. I waited for awhile, and then I snuck over to the side of the couch where Sally was sleeping. This was between the couch and the king bed where the twins were sleeping (as the couch faced the bed with a few feet between them). She appeared to be asleep, laying on her back. It was fairly warm out, so no one was using their blankets. I had an ice cube in one hand, and had the vague notion to slip it under some type of elastic or something to make it really stuck when she woke up. Usually when people woke up with the ice, it'd fly right out of their shirt as soon as they sat up. I had the devious idea that I could use the elastic of her bra, which would also give me the satisfaction (being a horny 19 year old guy) to actually touch her bra strap. As she was sleeping, I wouldn't feel quite as guilty about touching her.
I crouched at the edge of the couch near her head, looking downwards towards her shirt. I carefully grasped the edge of her t-shirt collar with my fingertips, and slowly lifted up the edge of her shirt from the top, and looked under at an angle. I could suddenly see not only the edge of her bra, but completely down her shirt. It was night time, but there was a ton of moonlight, and I could see very clearly. I could see almost her whole right breast (covered in bra), and between her breasts I could see some of her abs/midsection (she was in pretty good shape). She had something around a B cup, perfectly shaped (as only 18 year olds can have). She made some type of slight movement (or something else which scared me, louder breath, etc), and I dropped the shirt and ducked down to the side of the couch.
This was repeated a couple times (icecube since forgotten and melted on the ground). I'd gently lift the shirt, look underneath, she'd make some slight movement / noise, and I'd panic and "hide". I heard nothing beyond breathing from the other two sisters on the other bed. After a few times, I crept a bit lower next to the couch to be near her legs, and gently lifted the bottom of her shirt upwards. I could see even better from here (as the hem of the shirt lifted better than the collar). I could lift the shirt relatively high, and see her entire midsection, her bra covered breasts from below, up to her neck.
Again, she made slight breathing / movements, and I'd drop the shirt. Then I'd wait 30 seconds or more, and then go back to peeking underneath. Then I became more daring. I went to the top of the bed again, and gently lifted her shirt, and then used my fingertip to lift the edge of her bra, so that I could see underneath. I saw her nipple for the first time. I could see that the nipple itself was certainly hard, and I enjoyed looking at it closely, drinking it all in. Then she made another motion and I quickly dropped again to the floor.
At this point I was somewhat suspicious that she could potentially be awake, and just kept pretending to be still asleep. What I wondered was if she was awake, was she nervous / embarrassed to be in this situation with her cousin, or was she somewhat excited and playing along?
I peeked up another couple times, taking a careful look at both nipples under the bras. I was getting a bit less careful with my hands (slightly more strength holding up the shirt, pulling slightly harder on the bra to see underneath). Since she hadn't "woken up" yet, I wasn't sure if she was just a heavy sleeper, or again, playing along.
Either way, the 3rd or so time, she did some type of sleepy noise / movement, I hid, and she rolled over so her back was to me. I immediately thought she was perhaps hiding her front from me, as she might have been uncomfortable with the situation. Or a slight chance she was sleeping and just rolled over. At least that's what I told myself. On the other hand, she was still "asleep", so I waited for probably a couple minutes at least.
I gently lifted up the back of her shirt, and could easily see the back of her bra, with the clasp. I carefully reached up, and very gently grasped the clasp. I fiddled carefully with it for a bit, eventually getting it to unclasp and spring apart.
I did my normal hide thing for a few moments. No noise from her, and the sisters were still quiet. I then crept back up, and looked under her shirt. I put my hand up her shirt, and gently slid the bra strap slightly down her shoulder. She made some slight noise, and I hid again.
She rolled over again, and I hid for a couple minutes. When I peeked again, I saw she was once again on her back. Again, I was very suspicious she was awake, but wasn't sure if this was playing along, or trying to stop me. This was nerve wracking, since I was in a very awkward position. Any of our parents could step in at any moment, or any one of the sisters could wake up and say something. However, I also had an unbelievably hot 18 year old partially naked in front of me. I looked under the shirt from below, and could see that the bra straps were certainly loose. I carefully reached up, and could slightly pull the bra downward, enough so I could see the nipples poking out from above. Noise / movement again, I hid again.
I peek again, and see that the other strap is still on her shoulder. I gently move it off her shoulder. Noise / movement, I hide. I move up again, and start to gently slide the straps as far down as I can. I can't exactly remember how it worked out, but over a period of a few "hides", I slipped the straps off her arms. At this point I was very suspicious, since I was actually gently lifting up her arms and bending them to get the straps around her hands. I finally had each strap undone, and the bra was just sitting under her shirt.
Although I was very suspicious this couldn't be sleep, I kept up the pretense that I believed she was asleep. I carefully lifted up her shirt with one hand, and grasped her bra in the middle. I gently dragged it out from beneath her shirt. She continued breathing, though slightly heavier. I dropped the bra at the bottom of the couch. I looked under her shirt, and was able to see her breasts perfectly, both nipples pointing upwards, and her chest heaving somewhat quickly up and down.
I kept listening to her breathing, and watching for movement, waiting for any indication that she'd stop this game. I knew this was far beyond what I'd ever expected to happen, but my heart was pounding like mad, and I couldn't bring myself to stop. I pulled her shirt up slightly to reveal her tight stomach, and then slid my fingers carefully into the elastic band of her shorts. With extremely gentle motion, I attempted to pull the bottom of the shorts past her ass. I could feel resistance, even more than what could be expected from her weight. I could tell that she was certainly pressing her ass into the couch to prevent her shorts from moving downwards.
She still didn't admit to being awake at this point, so I knew I had the option to continue the game as well. I pushed harder into the couch, pulling the shorts downwards. There was some resistance, and then the shorts came easily.. she was actually lifting herself to allow the shorts to slide off! It was extremely confusing. Now I didn't know if she was letting me take them off to avoid a scene, because she wanted it, or because she knew she had no choice. In either case, I continued sliding the shorts down her legs. The legs were extremely light, and slightly assisted me in getting the shorts all the way off. I dropped the shorts onto the pile, and then took in the scene.