Sherry and I hatched the plot together, although I will admit that I was the instigator – and that I held a few things back, hoping to surprise her. Sherry is my brother Tom’s wife, and they’re probably my favorites of my four brothers and their spouses, although I’ll deny saying that if anyone quotes me. I do love them all, but Sherry and Tom are special.
Tom and I were always very close growing up, him being only two years older than me. That put us in the same school a lot, and he eased my transition first to middle school and then to high school, where he and his friends kept the other older kids from bullying us newcomers – or “scrubs,” as we were called then, although I have no idea why.
Plus, some of his friends were very cute, and with puberty behind me, I’d become very aware of them – and of the way they looked at me. Not that anything happened, or not until later anyway, but there was a growing awareness of the potential that guys represented and an undeniable attraction that I probably did not fully understand at the time!
Back to Sherry… she’s my age, so also two years younger than my brother, allowing for a few months' variation in our three birthdays, and we’d hit it off from the time they started dating seriously while they were both in college. When they got engaged and then later, when she became my sister-in-law, I may have been almost as happy as they were. I still tell Tom that she’s the smartest thing he’s ever done.
Sherry and I are close; I’m close with Tom too, but it’s on a different level with Sher, which is to say that she and I can and do discuss anything, including intimate things when the guys aren’t around. She’s my only family member who’s aware of the fact that Richard and I engage in extracurricular activities, that we enjoy threesomes with other men, and that Richie is bisexual. She was shocked to find out that I’d dipped my toes in that pond as well, with Gina – more surprised than she had been about Richard, it seemed – but she’d wanted every detail, and I know that hearing (and reading – she’s also my only family member other than my husband that knows about my Lush activities) the stories aroused her.
I, in turn, know more about her sex life than I probably should, given that Tommy, her sole sex partner, is my brother. There is, unquestionably, an ‘eeewww!’ factor in that, but it’s only fair that I listen to her since she so openly and avidly listens to me.
The bottom line is that he’s good in bed, she loves him and says he’s a considerate and fairly skilled lover, but (and this shocked me) he’s also the only sex partner that Sherry has ever had! I’d been in disbelief when she told me that she’d never had sex with any other men and had to apologize for making her feel self-conscious about it. I mean, it’s something to be proud of, I suppose, and for Tom’s sake I was glad… but wow!
But seriously, who even knew that ever happened anymore? I don’t think Tom has a vast well of experience, but I know for sure he’d had at least three girlfriends he’d fucked before he met Sherry, and I know now that her lack of experience sometimes bothers her.
She’d expressed interest in the past in expanding their horizons, opening up their sex lives a little, openly admitting she was envious of some of the things we’d done. She’s said she often wished she’d “played the field” a little before tying herself to one man, even though she loves him deeply.
One recent evening at their house in Denver, late, as she and I sat up chatting after everyone else had gone to bed, I asked her if my brother was at all on board for anything beyond married, vanilla sex.
She’d laughed. “Tommy? Yes, I think so. We use a lot of different positions, toys, and things, and he likes to fantasize about arousing scenarios.” She laughed, blushing. “I can’t believe I’m telling you this, but he loves those porn videos where guys’ wives get laid by other men. Those… well, they get his motor running! Also threesomes, with two women or two men.”
I smiled. “No need to be embarrassed, Sher, those are our favorites too, as you know, except we do it. We both enjoy it… which I guess raises the question of how you feel about it.”
“I… I’m not sure. It makes me very horny to see and think about.” She laughed again, self-conscious, I could tell.
“Would you want to do it?”
She shrugged. “I don’t know... I’d be afraid of hurting Tommy.”
“Never mind him for a minute; what would you want to get out of it?”
She considered that. “I think… maybe just making love to a different man. How he’d do things, how he would feel, his sounds, his scent, the way he tastes. That ‘someone new’ experience, something I’ve never really had. I mean, I had a “first-time’ experience with Tommy, which was very exciting…”
“And quick?”
She giggled. “A little quick, yes, in retrospect. You’re awful! To his credit, he made it very good.”
“I’m glad; he’s always been a very sweet guy; I’d expect nothing less.” I smiled. “How about cock size?”
“Rayne! I can’t believe you asked me that.”
I laughed. “I don’t mean my brother, I mean if you were to have sex with another man. Besides, I’ve seen Tommy naked – not aroused, but unless he’s a phenomenal grower, he’s only about average.”
With my parents, four brothers, and I all occupying a four-bedroom (by puberty I had my own room, the benefit of being an only daughter), two-bathroom/one powder room home, one of which was the master bath, which we messy young-uns were discouraged from using, it wasn’t that unusual to have to slip in and pee while someone was in the shower. Tom had gone to a local community college for two years and so lived at home until he turned twenty-one, at which time I was nineteen, so yeah, all supposedly “mature” and shit…
While I’d never gone out of my way to see him or any of my brothers, with a shared bathroom and glass shower doors, a common hallway, and a lot of curiosity, it was inevitable. Our parents, while they’d not been naturists or anything, had raised us with a casual attitude about nudity and our bodies. They were careful not to make us feel shame over something so natural, but at the same time to be sensible, and had been very strict and adamant about the four boys not harassing or teasing me sexually in any way. It had been a chaste curiosity about each other born of the logistics of a bunch of people occupying the same space, but I know we all looked if the opportunity arose, especially after we reached sexual maturity.
Sherry smiled. “He’s average, I guess, maybe on the smaller side, but really, it’s fine. He’s a wonderful lover, but it might be fun to try someone a little larger on for size, just, you know, out of curiosity.” She laughed self-consciously. “You have, right? I mean, you showed me the picture of Richard – and wow, by the way – and of your friend here in Denver, who was also very handsome, both nicely endowed. What’s your view on it? Does size matter?”
I covered that ‘showing of pictures’ in my Lush story, ‘My Very Special Friend’, so I won’t go into it here; just suffice to say she’d seen my husband’s package as well as that of a local older friend and very occasional sex partner, who were each better endowed than my brother, and Sherry was both appreciative and curious.
Now, I smiled at her. “I won’t say it doesn’t matter, but it’s not the be-all and end-all. The guy attached at the back end of it is most important… but yeah, a little extra size can be fun, even if only for the visuals and fondling!” Now it was my turn to blush. “I’m probably not as slutty as you might think, but I have experienced a little bit of variety.”
“I don’t think you’re slutty, I just think you’re fun and open-minded and love sex.”
“Thank you – and that’s all true. Plus, you know, I’m kind of a horny slut sometimes!” We both laughed, and I went on, “I’ve never been with anyone tiny, probably not less than small-average like my first boyfriend, but I’d assume there is such a thing as too small... not that a good, open-minded guy couldn’t learn a million other fun tricks to make up for it. There can also be too much of a good thing, Sher; I’ve had a couple of guys that were pretty damn big, which was intense, but I've seen are porn stars bigger - and no thank you!”
“Who are the guys you’re talking about, the hung friends? Anyone I would know?”
I thought a moment. “Umm, no I don’t think so. One used to be a rafting guide back when Richard and I both were, but he’s stayed with it continuously while I left and then came back, and Richard moved on to greener pastures.”
Richard had found a job that suited his education and now made good money, something raft guides don’t do; most of us do it because the thought of doing anything else is horrifying! Fortunately, he also loved his current job – maybe not as much as he’d loved guiding – but it had allowed me to get back to my first love, which was working for the raft tour company. For me, it had evolved into a year-round job rather than just whitewater guide season, and I did bookings, bookkeeping, presentations, PR, hiring, equipment acquisition and maintenance, and four-wheeling and horseback tours in the off-season, so my income had improved accordingly.
“Funny thing, Sher, but I couldn’t stand the guy – Jason - back then, and we never hooked up. He was just a big, arrogant prick with a big prick, which was his claim to fame, and it got him laid plenty, but I just hated his guts. Richard ran into him several months back, and – shock of shocks – he’d grown up! He mellowed and is now a very cool guy. A lot of fun, really.”
“Maybe you mellowed too, Rayney.”
“Moi? I’ve always been a cupcake!”
She laughed. “Yes, I’m sure! So tell me more about his big cock.”
I grinned at her. “That’s what I call getting to the meat of the matter! What can I say, Sher; he’s hung like a fucking Clydesdale. Serious penis bigness!”
She giggled like a schoolgirl! “Like, how big? Bigger than Richie?”
“Oh yeah – you saw the picture of Richard, hard? That’s about how big Jason is just dangling.”
“Fuuuck,” she breathed. “Wait, do you still have that picture of Richie?”
I laughed. “I’m sure I do.” I scrolled through my album and found it, handing her my phone, and had to smile at her eagerness as she took it.
“Damn… my brother-in-law has a very nice cock!” She expanded the screen, examining my husband’s genitalia closely – not that I could blame her; as she said, he has a beautiful cock. Handing my phone back, she said, “And this guy, limp, is about that size? Good Lord!”
“You can say that again – and it grows from there. Not proportionally, he doesn’t grow like Richie does, but it definitely gets bigger.”
“What, like a foot?”
“Feet don’t get bigger, Sher.” I grinned at her.
“Stop it, you know what I mean! How big?”
“This may surprise you, but I never put a tape measure on him. Richard is about eight inches though – him, I have measured - and you saw how thick. Jason is thicker, and maybe a couple of inches longer. He’s almost scary-big, but also super arousing-big. He barely fits in my mouth, thickness-wise.”
She laughed again. “Rayne, you’re terrible!”
“Well, you asked! I’m trying to give you a sense of scale.” I opened my mouth wide, and she laughed again.
“Did you fuck him?”
“Rhetorical question, right?”
She laughed as she shook her head. “I should know better than to set you up. You and your brothers never miss a chance to joke or tease. So, fucking this guy; how was that?”
“Jason… Oh, like I said, intense. It’s a little intimidating – I don’t even have any toys his size because they always looked uncomfortably big – but after playing with it, and sucking him, and him and Richard messing with me and…”
“Wait – Richie was there?”
“Oh, yes, of course! I wouldn’t have fucked Jason any other way, for sure not the first time. But as I was saying, I was so horny and wet that I probably could have taken him anyway – slowly – but I was sucking his cock, or doing my best to anyway, and Richie took me from behind, leaning up over my shoulder so we could both suck Jason at the same time.”
“Jesus, Rayne… I’m dripping!”
I laughed. “Me too! Reminiscing is fun. So anyhow, once Richie came inside me, it probably made it a lot easier to take Jason, me being used and messy, all super-lubed. It was unbelievable, feeling him enter me, and I came so fucking hard!”
She shuddered with arousal. “God! He didn’t hurt you?”
“No, not really. I mean, I knew it was someone very large, and that kind of burning stretch that’s more pleasure than pain, but my god… The sloppy seconds helped, though, for sure.”
She ducked her head, blushing. “I have to confess, I have a toy that’s about Richie’s size. I bought it online after you showed me his picture, so yes, I know that stretching feeling!”
“Nice, huh?”
“Oh yes! Wonderful… I’m glad Jason didn’t hurt you.”
I grinned. “Me too! I don’t know how he was when he was younger, but if his asshole attitude was any indication, he probably didn’t worry about causing pain for his partner. Now, though… well, he still swings a big bat, but he’s learned how to bunt.”
Sherry cracked up. “There’s that bad influence of your brothers on you again, what a thing to say! I can tell you grew up around a lot of boys, with that analogy. Oddly appropriate, though.”
“It is. Like all good athletes, even sexual athletes are always looking to add another move to their repertoire, tool to their toolbox, whatever.”
“So, he was a good fuck, I guess?” She blushed again – Sherry rarely talks like that!
“Oh my God, I came so hard, and so many times! Between the two of them, I was beat – and that doesn’t happen easily!”
She laughed. “I’m sure! But you don’t have any pictures of him?”
“I had a couple, but that phone died and I lost them. I do have several of the other guy I mentioned, my second big cock experience.”
“And who was this guy, your second?”
“This will sound terrible, but he’s our regular UPS driver.” I laughed. “So, how slutty am I now?”
She smiled. “Well, you probably had to come up with a Christmas bonus, right?”
“No, it was mid-summer. He delivered a new mattress for us and carried it in for me because Richard was out of town, and one thing led to another…”
“What, you were just thanking him?”
“Well, yes, but it was kind of for me too; I could have thanked him with just a blowjob.” She just shook her head, grinning. “I did call Richard and talk to him about it, and he encouraged me to go for it. He was in the Springs, and Seth was too, on business, so they were entertaining each other.” I laughed. “Horny little boys, you know.”
“I’m sure… but you said you have pictures of him, your UPS guy?”
I grinned at her. “I do. Would you like to see them? Only five dollars…”
“Don’t be mean! I’m dying here.” I opened my albums on my phone, scrolled to the pictures of James that I’d taken to share with Richard, and handed it to her. “Scroll left.”
