It was pure coincidence that my parents chose the exact two weeks to go on a second honeymoon that my husband, Mark was to be gone to a medical convention in New York. I happily agreed when they asked if my fifteen year old younger brother could fly out and stay with me while they were gone.
I hadn’t been able to spend much time with Eddie since getting married and moving from Atlanta to Dallas. Being seven years older, I’d practically raised him while our parents were both working. I hadn’t even seen him for over a year, and I couldn’t wait to see how much he’d grown.
I barely recognized him when he arrived at the airport. He had indeed grown a lot. He was at least six foot with broad shoulders, and he appeared very fit. I learned later that he’d really taken to working out since getting interested in playing football. He was always a good looking boy with unruly blond hair and beautiful blue eyes. Of course, it was his almost constant smile that I remembered most.
After a very long, very tight hug, we retrieved his bag and headed to my car. He had his arm around my shoulders the whole time hugging me close to him as we walked. It warmed my heart that he’d missed me as much as I had him.
On the drive home, it was football, football, and more football, but I didn’t mind. It wasn’t until I glanced at him one time and saw where he was looking that I realized he was a typical horny teenager. His eyes were glued to my tits.
I hadn’t thought anything about pulling on a pair of pink shorts and a white tube top. Of course, I wasn’t wearing a bra. I rarely did. Mark loved me going braless in public. He liked me to dress sexy . . . when I was dressed at all. I was hardly ever dressed at home, usually only when we had company over. Even then, my husband loved showing off his sexy young wife in revealing clothes.
For some reason I didn’t have to work very hard at staying in shape. I was five-nine, a hundred thirty five, with long blonde hair, blue eyes, long shapely legs and a chest full of firm DD cup tits.
I looked away from my brother and grinned, “So, do you have a girlfriend?”
“Not really. There’s one I like, but we don’t hang out away from school or anything. Her name is Sandy.”
“No hot make out sessions behind the gym or under the bleachers?”
“Nah, I’m really shy around girls. I get all tongue-tied and stuff.”
“Well, you’ve got plenty of time to get over all that.” As I was talking, I glanced his way again, and again he was staring at my tits. I let a chuckle slip out and looked away.
“I guess.” He responded in a less than convincing tone.
I was hoping I could make him feel better about his shyness, “You know, Eddie, when I was your age I was very shy around boys too. I guess it runs in the family.”
“No Way!” He sounded truly shocked.
I nodded, “Yep, all the girls teased me about it. They all had boyfriends, but I avoided boys like the plague.” I glanced his way and found him actually looking at my face this time.
“What did you do? How did you get over it?” He sounded genuinely interested.
“Well, if I had to point to one thing, it would be the family reunion we had in Florida. All of our relatives were there, uncles, aunts, and a bunch of cousins. One of the boys had a car and his driver’s license, so five of us went out to a nearby beach to swim and drink a little beer, three boys and two girls.”
“You’re lucky you didn’t end up in jail.” My brother piped in.”
“That’s true, but we didn’t get caught. Anyway, I’d never had beer, so I was feeling the results after a couple and it helped loosen me up. The other girl, I won’t tell you which of our cousins that was, but she wasn’t shy around the boys at all. Of course, she got more attention from them than I did, and I guess I was a little jealous. I forced myself to join in, telling dirty jokes, flirting, and there was a lot of sexual banter flying back and forth.”
“And you enjoyed that?”
“Yes, very much. I saw myself as sexy for the first time in my life. I’d developed quite a bit—nothing like now, but I did have a nicely developing body.”
“Were you wearing a bikini?”
I nodded, “Yes, but during the drive, I had a t-shirt on over it. I took it off shortly after arriving at the beach. That got me a lot of wolf whistles and compliments. I tried to act cool about it, posing and turning around, but I was scared to death inside.”
“I can see you doing that.”
“Yeah, now that’s nothing, but it was a big deal for me back then. I’d never done anything like that before. Everything went up a notch when we got in the ocean. There was a lot of splashing and dunking and stuff. At one point, one of the boys surfaced with her bikini top on his head. She acted like it was nothing. She just kept horsing around with them. Every once in a while I would hear her squeal and I figured someone was grabbing her tits.”
“So you were feeling left out again, huh?”
“Exactly . . . or at least until two of the boys dunked me and managed to get my bikini top off. I was glad they did that because, once I was topless too, I started getting my share of the attention.”
“Were they feeling you up and stuff?”
“Yeah, some—not a lot though. I guess they were afraid they’d make us mad if they tried to go too far. As it was, they were all three getting to feel of some tits now and then. They seemed to be satisfied with that.”
“So, that’s as far as it went?”
“Yes, except during the drive home, there was almost constant making out . . . and some more touching, of course.”
“That’s all it took to get you over being shy around boys?”
“Pretty much. It just changed my outlook and I felt more comfortable around them. We’re almost home. Are you hungry? Do you want to stop and grab a burger?”
“That sounds great.”
* * *
I almost let a laugh slip out when we got home. As we were going into the house from the garage, my brother carried our food sacks in front of his crotch. By the time I got into the kitchen, he was already seated at the table with his chair pulled up so close to the table, I’m surprised he could breathe.
When we finished our burgers, I showed him upstairs to his room and then left him alone. I walked up the stairs in front of him and never looked back. I didn’t want to do anything to make him more uncomfortable than he was. After all, he hadn’t stopped stealing glances at my tits every time he thought it was safe. I pretended not to notice.
Later, we had a nice supper and watched some TV. I had a couple of drinks and gave him a beer. Finally, I gave him a kiss on the cheek and went to my bedroom. On the way out, I gave him permission to have another beer if he wanted to.
In bed that night, all I could think about was Eddie’s shyness around girls. I was determined to help him, but I had no idea how. I just knew I had two weeks to figure it out.
* * *
I woke up early the next morning, took a quick shower and then got dressed. I chose a fairly conservative light gray halter and a pair of gray jogging shorts. The halter did leave a fair amount of the insides of my tits uncovered and a nice cleavage.
I could hear activity upstairs, so I went up in search of my brother. I found him in our large exercise room. He was jogging on the treadmill, and from the looks of his sweaty wife-beater, he’d been at it for a while.
When he saw me, he pulled out his ear buds and kept running, “Morning, Sis”, he said with a little wave.
“How long before you’re going to be ready for breakfast?”
“I’m almost done here. I’ll take a shower and be right down.”
“Okay, if you hurry, it’ll still be cool enough to eat outside.”
He nodded and replaced his ear buds.
* * *
When Eddie joined me outside on the patio, he leaned over and gave me a gentle kiss on the cheek. I’m sure he also took the opportunity to get a close up look at my tits. I pretended not to notice.
As we ate, I told him, “You know, you’re welcome to use the pool anytime you want.”
I spent the rest of the morning doing laundry and cleaning house while Eddie played video games in his room—or at least that’s what he said he was doing. After lunch, I explained to Eddie that I had to go shopping and that I’d be gone a couple of hours and that he should make himself at home.
“Can I have a beer?” He asked.
“Sure, just don’t overdo it. There’s no way I can carry you up the stairs.”
* * *
When I got home, I could tell my brother had a bit of a buzz. He wasn’t slurring his words or anything, but he was blatantly staring at my tits, and he didn’t try to hide the bulge in his shorts.
“How many beers have you had?” I asked him while standing in front of where he was sitting in the recliner.
He never looked up at my face as he held up his bottle, “This is my third, why?”
“Okay, but no more until after supper.” And then I decided to have a little fun with him in his buzzed state, “Have you been in the pool yet?”
“No, not yet. It’s really hot outside.”
“That’s all the more reason to cool off in the water. I’m going to change and head out there. You’re welcome to join me, but you’ll have to finish your beer or pour it into a plastic cup. We don’t allow glass out back.”
“Okay, I’ll be right out.” And he got up from the recliner and headed out of the room with his obvious bulge leading the way.
* * *
My most conservative bikini wasn’t very conservative at all. It showed a lot more skin than the halter I’d been wearing. The flimsy white material struggled to contain my firm, heavy tits. I had to chuckle when I appraised myself in the mirror. I was sure my brother would have a constant tent in his suit.
When it took Eddie quite a while to join me outside, I assumed he’d taken a few minutes to jerk off. I hoped he had. That would be even more of a compliment if he got hard again. Still, he was fifteen, so the thrill would be tempered by me knowing it wouldn’t take much, regardless of his having already jerked off.
Once he got in the water, Eddie never got out. I made sure to stay in the shallow end enough to give him plenty of chances to gawk at my barely covered tits.
I swam for another few minutes and then swam over to him. If it hadn’t been for his buzz, I would never have done what I did next. I put my arms around his neck and gave him a sisterly kiss on the cheek, “I’m so, so glad you’re here. I’ve really missed you. I hope I can make your stay here fun for you.”
And then I intentionally pressed my body to his. Sure enough, his dick was hard and poking me in the belly. I slid my hand down his body and gave his hard dick a firm squeeze while purring in his ear, “you should probably do something about this before supper”. Then I pushed away and walked up the steps, dried off, and entered the house without looking back.
* * *
I decided to stay in my bikini while I cooked supper. I had to chuckle to myself when I heard Eddie come in and go straight upstairs. I’m not sure why I was getting such pleasure out of keeping him horny. I knew I should stop but I was having too much fun.
When the Shrimp Scampi and garlic toast was ready, Eddie still hadn’t come back downstairs. I went up and knocked on his door. When there was no response, I knocked louder and then louder, calling his name.
Finally I cracked the door open and peeked inside. My brother was lying on his bed in his jockey shorts sound asleep. “Ahh, the beer.” I whispered to myself. I also had to smile when I noticed his boner. The head was sticking out above the elastic, “Nice”, I whispered to myself again. Then I quietly left his room and closed the door.
When I got back to the kitchen, I put supper back in the oven and turned it on low to keep it warm. “Supper can wait.” I said to no one. And then I went into the den and fixed myself a drink.
* * *
When Eddie finally came downstairs, he looked freshly showered and he had on a clean pair of shorts and a t-shirt. “Have a nice nap?”
“Yeah, I smell food. Is supper ready?”
I laughed, “Only for about two hours. When I couldn’t wake you up, I put it back in the oven to keep it warm.”
“Sorry.” He said in a sincere tone.
I put my hand on his shoulder on the way into the kitchen, “Don’t worry about it. Oh, and by the way, nice tidy-whities.”
My brother stopped in his tracks but I kept going to the oven. “You . . . you came in?”
“Yeah, sorry about that, but I knocked until my knuckles were sore. I was worried about you. Don’t worry, you weren’t naked or anything—not that it would have bothered me if you had been. I’ve seen you naked before. I used to bathe you, remember?”
When I turned toward the table with the Scampi, he was giving me a scolding stare. “I’m not a little kid anymore.”
I sat across from him and looked him right in the eyes, “Trust me, I noticed. Speaking of which, did you take care of that not so little . . . condition?”
God! I don’t think I’ve ever seen such a bright shade of red. He was sitting there staring at his food, so I thought I’d lighten the mood. I let out a silly giggle, “You don’t have to answer that. Of course you did.”
Eddie was totally silent during the remainder of supper. Then he helped me rinse the dishes and load the dishwasher. During that time, I never once caught him staring at me. Finally, I told him to go have a seat in the den, “I’ll be there in just a minute.”
* * *
When I got to the den, I expected him to be sipping on a beer, but he was standing at the wet bar instead. “Whatcha doing?”
“I was going to have a glass of what you drink, but I don’t know what it is.”
“Oh, you think you’d like to try some whiskey, huh?”
“Yeah, if it’s okay.”
While I was showing him where the ice was and how to mix a Jack and Coke, I said in a serious tone, “I’m sorry if I embarrassed you earlier . . . in the pool and a few minutes ago during supper. I wasn’t trying to. I was just trying to loosen you up a little.”
As we were sitting, he in the recliner and me on the end of the sofa, he said, “Don’t worry about it.”
“It’s a compliment, you know.”
“What is?” He said turning to look at me.
“When looking at me makes your dick hard.”
It was a good thing I’d made his drink mild because he took a big gulp and shuddered before saying, “Then consider yourself complimented.”
“Then thank you, Sir.”
“You don’t think it’s weird?” he asked in a serious tone.
“A guy getting hard from looking at his sister.”
I let out a loud laugh and shook so hard I almost spilled my drink. When I could, I looked right at him and said, “Eddie, your dick doesn’t know I’m your sister. It just sees a sexy girl. Now, please don’t think I’m all full of myself. I’m not. I’m a realist. I know what I look like. And when a dick appreciates the way I look enough to get hard, I take it as a compliment. And if the dick’s owner jerks off because of me, that’s an even bigger compliment. It doesn’t matter how old or young he is or what he looks like, and yes, even if he’s my brother.”
He emptied the last of his drink, shuddered again, and then got up and walked over to me to take my empty glass. He didn’t try to hide the bulge in his shorts.
I pointed to his crotch, “That looks uncomfortable. Feel free to adjust it if you need to.”
As he was walking to the wet bar, he said “It’s kinda pointless in jockey shorts.”
I laughed, “Well, then lose the jockey shorts.”
I watched my brother walk behind the bar. He sat our glasses down then bent over. When he straightened back up, he showed me his jockey shorts in his hand and tossed them on the floor. And then he set about to mix our drinks.
As he was handing me my glass, I let out a chuckle. “What?” he asked.
I pointed at his crotch again, “It still looks uncomfortable. You need some looser shorts.”
“I have a pair upstairs.”
“Just one pair?”
“Yes, and my workout shorts.”
“Then why don’t you go change into them. I’ll buy you some more tomorrow. I don’t want you staying uncomfortable the whole time you’re here, and I have a feeling you’re going to stay hard a lot.”
My brother nodded and actually let out a chuckle, “You’ve got that right.” And then he retrieved his jockey shorts from the floor and headed for the stairs.
* * *
I was surprised when Eddie came back downstairs after only a couple of minutes. I had expected him to jerk off while he was up there. It was obvious he hadn’t, as his dick was still causing a huge tent in his looser shorts. He also surprised me by walking right up in front of me and asking, “Better?”
I let out a little laugh, “You tell me. Are you more comfortable now.”
“Much.” He said as he sat down and reached for his drink.
I’d mixed his first drink very mild and he’d barely touched the one he mixed for himself, so I was fairly certain it wasn’t the alcohol causing him to seem more at ease. I got the feeling he was enjoying the attention to his dick and not having to be embarrassed about it being hard.
I decided to keep it going, “I’m surprised you didn’t jerk off while you were upstairs.”
His face got red, “Did you want me to?”
I studied his expression and came to the conclusion his question was sincere. “Eddie, do you know when I’d like you to jerk off?”
He shook his head, “No”
I showed him a warm smile, “Any time you’re in the mood to do it. That’s when I’d like you to jerk off. I’m sure you have to sneak around to do it at home, but you don’t here. I want you to feel free to do it any time you want.”
“Just like that, huh?”
I finished my drink and went to the wet bar for another, but I paused on the way by to look down at him, “Just like that. That’s when I do it, and you should feel free to do the same.”
While I was mixing my drink, my brother stammered out, “But . . . but you’re . . . married. “Why do you, you know?”
I let out a big laugh, “Eddie, married people jerk off too. Hell, Mark and I watch each other do it sometimes. Other times we do it together. When he’s out of town, sometimes I’ll Facetime with him and let him watch me. Your bedroom is right over mine, so I’m sure you’ll hear me sometimes. I’m not going to force myself to do it quietly just because you might hear me. Any more questions?”
“Like on the internet . . . the women on there get really loud.”
I sat back down and looked at him, “No, not like that. What you see on the internet is ninety percent fake. The only time I get loud is when I’m cumming really hard. That’s usually on my third or fourth orgasm. The rest of the time, you won’t be able to hear anything.”
“That’s kinda what I thought.”
“Now, when Mark is home or watching me on Facetime, I’m a lot louder, more like the women in the porn movies. He likes me to be loud when I’m whacking off and when we’re fucking, so I do it for him.”
“Wow? What about that surprises you?”
He shrugged, “Just that we’re talking like this, I guess. Why does he like you to be loud?”
“I’m not sure. I guess it just confirms in his mind that I’m really enjoying it.”
“Does he last a long time?”
I almost choked on my drink, “Long enough for me, why?”
He shrugged again, “I don’t know. A lot of the guys in the chat rooms brag to the girls about how long they can last. I’m afraid I won’t be able to.”
“Oh, how long do you usually last?”
His face got red, “Only a couple of minutes the first time. A little longer after that.”
I considered his answer for a few seconds. I’d helped Mark learn to last longer. “Teenage boys don’t mean to, but they actually train themselves to cum fast. They are afraid of getting caught, so they hurry to get it over with fast. You have to train yourself to last longer.”
“Look up the ‘squeeze technique’ on the internet. It’s a way to squeeze your dick just below the head right before you start cumming. The more times you stop yourself from cumming, the longer you will train your dick to last.”
My brother’s jaw was agape, “How do you know about something like that?”
I laughed out loud, “I’m married to a doctor, remember? I helped him.”
“Cool! I’ll have to try that.”
“Just remember, it won’t happen overnight. You’ll have to practice it. And then over time, you’ll last longer and longer.”
He let out a chuckle, “I won’t mind practicing that. Thanks, Sis.”
“Okay then, you’ve had enough to drink. You go on upstairs and look it up before you jerk off. I’m going to have one more drink before I go to bed.”
We both got to our feet and I gave him a tight hug and a peck on the lips. I wasn’t shy about pressing my body against him. His dick was rock hard, so I slid my hand down and gave it a firm squeeze while I purred in his ear, “Good night, Eddie, enjoy.” I waited until he was headed out of the room to call out, “Practice, practice, practice, and let me know how it goes.”
That night, I had no problem getting myself off several times. I made sure to be loud enough for my brother to hear me when I came.
* * *
Once again, Eddie was jogging on the treadmill when I finished my shower and dressed. I’d chosen a fairly conservative halter and shorts. “Breakfast in thirty,” I told him. He just smiled and gave me a thumbs up.
“Well, how did it go last night?” I asked him while we were sitting across from each other eating breakfast.
His shoulders slumped noticeably and he lowered his eyes to his plate. “Not very good.”
“Oh, what happened?” I asked in a sympathetic tone.
“I . . . I was too slow applying the squeeze the first time.”
I chuckled, “The first time?”
“Yeah. It seemed to work the second time, but the minute I released the squeeze, it started cumming.”
I reached across the table and put my hand on his, “It’s okay. Don’t worry about it. You’ll get it. You just need more practice.”
“Okay, but I tried again this morning and it still didn’t work.”
“Hrm . . . okay, I’ll tell you what; for today, you just keep trying. It’s better to apply the squeeze too soon rather than too late.” And then I got to my feet. “I’ll be right back.”
I’d chosen the more conservative halter because I was going out, but now I was wishing I’d chosen something sexier. I wanted him to have something to think about while jerking off, so I hurried to my room. I doffed the halter and replaced it with the smallest string bikini I owned. It barely covered my nipples and left most of my areolas exposed.
When I returned to the kitchen, my brother let out an appreciative “Wow!”
I giggled while sitting down and told him, “I’m going out to buy you some new shorts, and I wanted to give you something to think about while I’m gone.”
“Can I ask you something?” He was staring straight at my tits.
“Eddie, you can always ask me anything . . . and I do mean anything. You don’t have to be shy. If you have a question, just ask.”
“How . . . how do you keep it where it’s supposed to be?”
I giggled, “It slips off a nipple now and then. That’s half the fun of wearing it. No one knows when it will slip off, so they keep watching.” Of course, what I didn’t tell him was that I knew exactly how to make it slip off a nipple anytime I wanted.
“I know it’ll keep me watching?” He said in a reverent tone.
He was still eating when I got up and put my dishes in the washer. When my back was to him, I shrugged my right shoulder, causing the tiny strip of material to slip off my right nipple. Then I turned back and walked over to him. “I’m going to put my halter back on and then head out.” And I bent down and gave him a kiss on the cheek. When I straightened up, I glanced down and pretended to just realize my nipple was exposed. “Oops, sorry.” And I slowly pulled the material back in place.
He didn’t respond, so I just turned and headed for my bedroom. “Put your dishes in the washer when you’re done.”
Eddie was just rinsing his plate when I went back through the kitchen on my way to the garage. He was wearing the same loose shorts he’d changed into the night before, and when he turned around his dick was rock hard and sticking out proudly. An idea hit me so I told him on my way by, “While I’m gone, and after you jerk off, you should try skinny dipping in the pool. It feels amazing.”
“How . . . how long will you be gone?”
“I’m not sure. Why?”
“What if you . . . you know.”
I laughed, fully understanding he was worried about me returning while he was still in the pool naked. “Don’t worry about it. If you’re still in the pool when I get home, it won’t be the end of the world. Hell, I may even join you.”
* * *
It didn’t take me long to pick out some loose shorts that wouldn’t restrain my brother’s hard dick. The three I purchased were all extremely sheer. I like the white ones the best because I knew I’d be able to see pretty much every detail of his hard dick. All three I bought were white.
I almost headed straight home, but I thought better of it. If I got home too soon and Eddie was still in the pool, it wouldn’t mean anything. But if I killed some time and he was still naked in the pool, I would take that to mean that he was staying in the pool longer in hopes that I’d come home while he was still in there and join him.
I pulled into the garage an hour and a half after leaving. I draped the new shorts on a chair and set the large bottle of Jack Daniel’s on the table. And then went to the den to peek out the window. Sure enough, my brother was still in the pool . . . and he was naked.
It took me a minute to decide on a course of action. When I had it, I walked out the back patio door still dressed. “Hey, enjoying your swim?”
“Yeah, I was just about to get out.”
I showed him a pouty face, “Bummer. I was going to join you.”
“I can stay in a little longer.”
I had to suppress a laugh that was struggling to spill out. “Great!” and I immediately untied my halter and tossed it aside. I wasted no time doffing my shorts and thong. Then I went over to the steps and slowly walked down into the water.
After submerging myself totally in the shallow end, I stood up, putting the water line just above my belly. I raised my elbows high and fussed with my hair for a minute before starting to swim to the other end. Eddie was hanging onto the side of the pool in the deep end.
I eased up beside him, “So, how do you like skinny dipping? Isn’t it wonderful?”
“Yeah, it’s fun.”
I was just close enough to him to smell whiskey on his breath. I started to call him on it, but I decided to ignore it. To me, that was confirmation that he had intended to still be in the pool when I got home, regardless of how long he had to wait. “Well, did you jerk off after I left?”
He didn’t hesitate, “Of course.”
He shook his head, “I just can’t get the hang of that squeeze thing.”
I put my hand on his arm, “Don’t worry. We’ll figure it out.”
I pushed off the wall and floated on my back, insuring he would have a great view of my tits. I was never good at floating on my back, so I began to sink when the momentum of pushing off died. I was treading water in the deep end, “Shit! I can’t float on my back worth a shit. I’ve been trying to learn it. Do you want to help me?”
“Sure. What do you need me to do?”
I giggled, “Meet me in the shallow end.” When he was close enough, I told him, “Stand up and when I lay back, put your hand under the small of my back and support me.”
I was laughing hard inside. I knew he was getting an up close and personal look at not only my tits, but my shaved pussy as well. I closed my eyes so he wouldn’t be shy about looking.
Without opening my eyes, I asked him in a sincere tone, “Have you ever seen naked tits in person?”
He cleared his throat, “No—Mom a few times, but nothing like this.”
“Then you’ve probably never seen a pussy in person either, huh?”
I smiled, “Good. I’m glad I’m your fist.”
“Because you don’t have to be nervous about it with me. You can just relax and look all you want.”
“Okay? That’s all you have to say?”
“I’m . . . glad it’s you too.”
I put my feet down and stood in front of him, “That’s enough floating for now. We can practice some more later.” And then I looked him right in the eyes while I reached down and slid my hand around his hard dick. Still holding it, I asked him, “Are you ready to go up and jerk off again?”
“Y . . . yes.”
“Okay” and I gave him a lingering kiss on the lips. “I’m going to stay out here for awhile. After you dry off, will you bring me a clean towel and a drink in a plastic cup?”
“Uh huh” he said in a strained voice.
“Enjoy your jerk off, and don’t forget to squeeze, better early than late.” And I released his hard dick and fell backward into the water.
* * *
I hadn’t intended to hold onto his dick that long, but if felt so good, I just couldn’t force myself to let go of it. I blatantly watched my brother as he got out and dried off and until he disappeared into the house.
When he came back out, he dropped the towel on a chase lounge, then walked over to hand me my drink. As he was handing it to me, I showed him a wink and said, “By the way, you have a beautiful dick, Bro.”
“Thanks” he said as he straightened up and shook his hips, making his dick swing from side to side. And then he chuckled and said, “I guess I should go take care of him.”
“Practice, practice, practice” I said with a giggle.
* * *
I was being honest when I told him I thought his dick was beautiful. Before Mark, I’d only been with two guys. Neither of them were worth remembering. Mark was a wonderful lover. He was thirty one when we met, which didn’t make my parents happy. His dick was about average, I guess, but he always made me cum many times, especially after we’d trained him to last longer.
Eddie’s dick looked a dab longer and a little thicker. I tried not to think about how nice his extra thickness would feel inside me. I sat on the steps and sipped my drink for a minute or two, and then got out sat in the shade of the umbrella. Finally, I dried off, got dressed, and went inside to fix us some lunch.
* * *
When Eddie came downstairs, I told him, “Sorry, I didn’t feel like cooking, so I just made us some turkey sandwiches. I made you two. You’re a growing boy . . . and you’ve been exercising.” I added with a giggle.
“So, how did it go?”
His shoulders slumped again, “Same. It doesn’t matter how early I do the squeeze, the minute I release it, I start cumming.”
“Hrm, oh well, we have time to figure it out. Eat your sandwiches and then try on your new shorts.”
He picked up a pair of the shorts and examined them. Then he let out a chuckle, “I’m not going to be wearing these in public—not commando anyway.”
I laughed, “That’s why I picked them. I’m sure I’ll be able to see your dick clearly through their sheer material.”
My brother got a confused expression on his face, “You . . . like seeing it?”
“Yes. I may be your sister, but I think you have a beautiful dick.”
“Then why . . .”
“Why don’t you just go naked?”
“The same reason I don’t. If you see something too much, the new wears off. That’s what happens to married people. They see each other naked so much; it loses the freshness and excitement after a while.”
“I guess, but I’d never get tired of seeing you naked.”
I laughed, “You might not get tired of it, but your dick’s reaction would diminish over time.”
“If you say so.”
I waited until he’d finished both of his sandwiches, and then told him, “Time to try on your new shorts. They’re all the same, so you only need to try on one of them.”
“Okay, I’ll go change into them.”
I laughed, “Don’t be silly. Do it here.”
It wasn’t until he stood up that I realized his dick wasn’t hard. When he lowered his shorts, I got my first look at his flaccid dick. I was surprised to see that it was almost as big as when it was hard. Mark’s shrank up a lot.
When he had the new shorts on, I could almost make out the head of his dick through the sheer material. “Very nice” I said in a sincere tone. “I guess we’ll have to wait until you get hard to see how comfortable they are for you.”
“I’m sure they’ll be fine.”
“We’ll see. Anyway, I’m going to take a nap. You can play your video game, watch TV, go swimming, whatever you want to do.”
“I’ll be fine. Enjoy your nap.”
Just before leaving the kitchen, I turned and said, “No jerking off, okay? I want to try something different later.”
* * *
I tossed and turned trying to go to sleep for thirty minutes or so. I couldn’t stop thinking about my brother’s dick. I loved feeling a soft dick in my mouth, lolling it around with my tongue and feeling it grow. Mark grew a lot, and I loved that, but I couldn’t stop imagining how awesome it would be to have a soft one in my mouth the size of Eddie’s.
I finally gave up, pulled on a light robe and went to the den. I mixed a stiff drink and sat in the recliner. As I sipped my drink, the images of my brother’s dick, both soft and hard stayed in the front of my mind.
I assumed Eddie was either up in his room or out at the pool, so I slid my hand inside my robe and began kneading my tits. Before long, I sat my drink aside and moved my other hand to my wet pussy. I leaned the recliner back some, then put my head back and closed my eyes.
It didn’t take long for me to bring myself to my first orgasm with a second one shortly after that. I didn’t want to go too far. I had plans for that later, so I stopped and set the recliner upright. Then I got my drink and returned to my room. I was asleep in no time.
* * *
After a nice supper of spaghetti and meat sauce, I told Eddie to go to the den. And then I went to my room and donned that tiny nothing of a bikini again. In the den, I handed him a medium strength drink and told him, “Just two tonight. I don’t want to hear later that I’ve turned you into an alcoholic.”
While we were sipping our drinks, I asked him, “So, earlier, after our swim and you went upstairs to jerk off, I want to know exactly what you did and how. I want details.”
He shrugged, “There’s not much to tell. I was already naked, so I just lay down on my bed, closed my eyes, and started stroking.”
That was pretty much what I thought. “I see. What did you think about when you closed your eyes?”
“You floating in the pool.”
“Outside of seeing a woman totally naked for the first time, what about it were you thinking about?”
“That’s about it, except . . .”
He thought for a few seconds and took another sip of his drink, “When you closed your eyes and I was right there . . . so close, and you weren’t watching me . . .”
“You felt freer to look?”
“Okay. Now, were you thinking more about my tits or my pussy?”
“Both . . . back and forth between them, I guess.”
“That’s fair. So were you stroking your dick fast or slow?”
He was just finishing his drink, so I said, “Okay, that’s all the questions I have for now. I want you to get up and come over here and stand in front of me.”
He was wearing his new white shorts and his dick was mostly hard, but not as hard as it had been in the past. I wanted it to be fully hard. “Eddie, take off your shorts and t-shirt for me please.”
My brother didn’t hesitate. He pulled his t-shirt over his head, lowered his shorts and kicked them away. I swallowed the last of my drink and held out my empty glass to him. “Make me another please, but only me. You can have your second one later.”
While he wasn’t looking, I slipped off my bikini bottoms and top. When he turned around, his eyes popped open. I was delighted to see his dick was fully hard by the time he got back to me with my drink. “I thought you might like a better look at a pussy. Am I right?”
“Y . . . yes.”
I sat back on the sofa and pulled my feet up to my butt and spread my knees out as far as I could. “I’m not going to close my eyes, but I want you to feel free to look. You can kneel down and have a closer look if you want.”
My brother was on his knees in a flash. His face was probably three feet from my pussy, so I said, “You can get closer. Do you know all the parts?”
“Good boy” I said with a chuckle. “I’ve touched you dick several times, so turn about is fair play. You can use your fingers to spread my pussy open so you can see it better.”
He did just that. Of course, his hands were shaking so violently, I’m surprised he could accomplish even that simple task. When he had me spread fully open, I asked him, “Well, what do you think? Is it what you expected?”
He nodded, “Yes, but it looks better than the ones I’ve seen online. It’s so pink . . . it’s beautiful.”
After about five minutes, I told him, “Okay, stand up.” When he was standing, I said “Now, I want you to show me exactly how you have been applying the squeeze.”
When he did, it looked to me like he was doing it right. “How hard have you been squeezing it?”
“As hard as I can.”
I told him to release it, and then I put my feet on the floor and scooted forward on the sofa. I then reached out and applied the squeeze to his dick. “Have you been squeezing it this hard?” and I really clamped down on it.
“Yes, maybe harder than that.”
I released his dick and sat back again, “Okay, how long to you squeeze it?”
“Only a few seconds the first time, but I’ve been holding it longer and longer each time, probably a full minute last time.”
“Go mix yourself another drink, better mix this one a little stronger since it’s your last one tonight.” God! I was already getting so horny, it was taking all of my restraint not to throw him down and fuck his brains out.
When he returned with his drink, I told him, “Okay, just stand in front of me. Keep your drink in one hand and start stroking your hard dick with the other. Do it slowly, very, very slowly. Don’t jerk off. Just play with it. After a dozen very slow strokes, stop and play with your balls, then stroke it some more. Remember, you’re not jerking off. You goal isn’t to cum, it’s just to enjoy the feeling of your hand on it. But, if you feel any hint that you might be getting close to cumming, apply the squeeze and hold it until I tell you to release it.”
I watched him closely for the next ten minutes or so. The sight of it was driving my pussy crazy. “Okay, stop and apply the squeeze. Hold it until I tell you to stop.”
He complied obediently. I had him hold the squeeze for over two minutes. “You can release it now.”
He did, “Okay, now what?”
I drained the last of my drink and got to my feet. “You did great. Let’s go swimming.” And that’s what we did.
He was helping me float again when he announced, “I need to pee.”
“Yeah, me too.” I confessed. “C’mon” and I led him out of the pool and onto the grass. I immediately squatted and started peeing. He was just standing there with his jaw open. “What are you waiting for?”
“It’s . . . I don’t know if . . .”
“You mean because I’m watching, or because your dick is hard?”
I laughed, “Well then you’ll just have to stand there and concentrate. It should be easier out here than down into a toilet.”
“You’re going to watch?”
“You watched me. Now get on with it. I don’t care how long it takes.”
Actually, it didn’t take him that long. He managed to get a small stream going and then the dam burst and his pee was arching high into the air. A half minute later, we were back in the pool.
“See, that wasn’t so bad, was it?”
“Nah. Like you said, all I had to do was concentrate.”
“That’s just one more silly hang up we’re going to work on while you’re here.”
“What, peeing while I’m hard?”
I laughed, “Yes, and doing it with me watching.”
“But . . .”
I put my hands on his shoulders and looked him right in the eyes, “Eddie, I love watching it . . . and I love watching you jerk off.” Then I moved one hand down his body and gripped his hard dick, “And I love feeling of your hard dick.”
“You like me touching it, don’t you?”
“Y . . .yes, but . . .”
“I . . . I’m afraid I might . . . you know.”
I immediately moved my fingers and applied the squeeze to his dick. “Don’t worry; I’ll let you cum later, but not yet.”
“Can I please have another drink?”
“Okay, but after I’m finished squeezing your dick. I don’t want to risk you cumming until I’m ready.”