21 Kasım 2023

Brother Gets Caught Ch. 2


This is the second and final part of a true experience that happened recently. I’m still coming to grips with the wrongness of it, but I find it extremely arousing to think about, especially given the lack of sexual intimacy with my wife as noted in Chapter 1.

* * * * *

Strangely enough, not a word was said the next morning about what had happened between us; I think we were both shocked by the experience, and an interval of time was probably necessary before we confronted it. The day went wonderfully…a post-wedding brunch, visits to relatives, shopping, and a big family farewell dinner that, of course, provided an opportunity for more imbibing. As happened the previous two nights, Jessica and I got ready for bed separately, and once we were in bed, engaged in some small talk about the fun day we’d just experienced. I was content to let the previous night’s situation pass into history, but it seems Jessica wasn’t.

“I hope you’re not upset about what happened last night.”

“No, not at all,” I replied. “Thanks for being so cool about it – it was just kind of embarrassing for me.”

“You shouldn’t be embarrassed about it. It’s nothing to feel bad about, and I couldn’t stand to see you suffering.”

“Thanks…it’s tough dealing with Amy sometimes. She’s a great wife and everything, but she just isn’t very sexual. I’d love to have that closeness with her.”

“Yeah, last night you seemed to respond pretty well when you were thinking about her,” Jessica said with a laugh in her voice.

My embarrassment returned briefly…this was an intimate topic that I’d never imagined discussing with anyone, least of all my sister. Jessica was not going to let this drop, and the conversation was headed in an unexpected direction again. But this time I felt myself getting over the embarrassment sooner, and my arousal returned…I was unmistakably becoming erect.

“Um, yeah,” I stammered.

“Do you always think about her when you’re doing it?”

I couldn’t even imagine telling Jessica that I had thought about her the previous evening. “Yeah, it’s pretty much what I think about.”

“I think it’s sweet the way you think about her when you’re doing it. God, I wish a guy would think about me when he was doing it!” Once again…if she only knew. “It’s been so hard for me to develop any kind of lasting relationship with a guy. I’m so focused on work, and that’s where I put a lot my energy. Plus there aren’t exactly a lot of guys lined up to sweep me away.”

“Oh, come on,” I replied. “You’re bright, you’re successful, you’re cute…any guy would be lucky to have you.”

“I don’t know. I just don’t think really highly of myself sometimes. I’m fat, I’ve got too much hair, and gravity is catching up with me.”

“Jess, you’re too tough on yourself. You’re not fat at all, and you’re one of the most beautiful people in the world, inside and out.”

“I see how guys look at other women…they never look at me that way. You think your sex life is bad…mine’s even more dismal.”

“Two pretty poor specimens of humanity here, huh?,” I offered, in an attempt to brighten up the conversation. Our intimacy of conversation over the past twenty-four hours was causing my mind to continually cycle back to sexual images, and apparently the previous evening’s episode had caused Jessica to focus on similar matters.

“Steve, do you need to do it again?” Jessica asked softly. “You can think about Amy again if you want.”


“I thought so,” she said with a giggle. “Tell me about Amy’s body if that’s a turn on for you.”

Giving myself the mental go-ahead seemed easier this time, and I instinctively reached down and started to caress myself. Having the room pitch-black helped. “Well…I love the way her breasts stick out…and I really love her butt.”

“I know what you mean. We changed in the same dressing room once, and she’s in great shape…especially after two kids. I couldn’t believe how great her boobs still looked…God, I think mine are halfway down my stomach by now. I bet she even looked good pregnant.”

Jessica was right…Amy did look good pregnant, and I had masturbated many times thinking about her enlarged breasts and darkened, engorged nipples. It had been a big thrill for me to masturbate into her bigger-size pregnancy bras and panties. But she never let me lay a hand on her sexually throughout either of her pregnancies.

“Yeah.,” I said haltingly as I began to touch myself more vigorously. I was still careful to not make any overt noises as I masturbated, even though Jessica knew that I was aroused. Strangely, I found myself thinking about what Jessica would look like in her underwear…and wishing I had her bra and panties to explore. I pictured her bra as having a fair amount of support so that her tubular breasts could appear more rounded. And I assumed that her panties were somewhere between sexy and matronly…probably some sort of brief cut. My arousal increased as I imagined her Bomonti Escort standing before me…her breasts filling her bra cups…her wide hips filling out her panties…her pubic hair spilling out the top and sides, forming a large bulge in the front panel.

“Are you doing it now, Steve?”

“Ummm…yeah, I couldn’t help myself with the way we’ve been talking.”

“Steve…it’s OK…you know what?”

“What, Jess?”

“I’m doing it too.”

I inaudibly gasped and tensed. This strange sibling situation was now even stranger with Jessica masturbating also. For the first time, I regretted the darkness of the room. I created a mental image of what she must look like pleasuring herself, with her vision from the shower still fresh in my mind. I quickly tried to think of something reassuring to say…something that would let her know that I treasured her candor. But, as usual, I foundered.

“Really? Wow.” I wasn’t adding a very articulate element to our conversation.

“Hey…I get horny too. You’re not the only one who’s getting turned on.”

Hearing Jessica use a relatively raw sexual term had the same effect on me as it did the previous night. “This is so weird, Jess.”

“No it’s not. We have the same needs as everyone else. You can think about Amy, and I can think about one of the guys I work with…that usually gets me going.”

“I guess so, but don’t do anything you’re not comfortable with because of me.” Jessica was clearly leading this situation, but for some reason I felt compelled to continually apologize for any discomfort, imagined or not.

“Believe me, I need to do this too. The pitch of her voice had changed slightly, and I could detect that her arousal was increasing as she masturbated. “This feels so good.”

“Me too,” I added feebly as I lovingly stroked my erection. Instead of thinking about Amy, I focused solely on Jessica’s body. I once again reveled in her sexiness…the way her breasts hung at the sides of her ribcage, her cute rounded tummy, her pubic bush, and her luscious rear end.

After a few silent moments, I heard her making motions in her bed, as if she were changing positions. “Jess, you OK?”

“Yeah…this may sound weird, but it’s better when I lie on my stomach when I’m doing it.” Her movement stopped, and I heard her sigh and then softly moan for a brief second. I suspected she had resumed masturbating, and as I touched myself I pictured what she must look like…her hand moving over her pubic area, her other hand perhaps caressing her sexy breast, and her curvy butt rising upward from her body. “You still thinking about Amy?”

As close as my sister and I were becoming, I still couldn’t let on that I was really thinking about her. “Yeah…I want her so much.”

“Just imagine you’re in bed at home with Amy, making love. And she’s in the same position I’m in. I bet she loves that…I know I do.” Well, no, she definitely doesn’t love that, but it didn’t stop me from switching my masturbation imagery from Jessica to Amy, thanks to Jessica’s suggestive talk. I fantasized about seeing my beloved Amy lying next to me on her stomach and then asking me to make love with her in that position. I move on top of her, and, feeling my body against her petite rounded butt, I begin intercourse. In the fantasy I actually last longer than a minute before I ejaculate my semen into her vagina.

“It’s so nice to think about that, Jess.”

I could now easily hear Jessica’s labored breathing, and I became intensely aroused when I heard her slight moans become more frequent. “Michael…Michael…,” I heard her whisper almost imperceptibly. I surmised Michael is her co-worker, and in any case, I didn’t want to interrupt her reverie to question her choice of fantasy lover. Jessica’s obvious arousal was putting me over the top; abandoning any sense of propriety, I pushed the covers down and aggressively increased the speed and strength of my stroking. I was aware of the headboard slightly hitting the wall and the bed shaking in rhythm to my pumping.

A few feet away, Jessica continued her loving self-pleasure, and for the first time I could hear friction against her sheets and a slight rhythmic moving of her bed.

I thought about how lucky Jessica’s past lovers were…they had the opportunity to make love to her and experience her body intimately. I pictured her and one of her suitors lying naked on her bed in her apartment, kissing and starting foreplay. His hands roam her fleshy body, concentrating on her breasts and rear…and her hand grasps his large penis and lovingly caresses him. I imagine him making love to her from behind, helping her onto her hands and knees as he positions his penis behind her. Her breasts hang down sensually, even narrower than when I had seen her in the shower…and her tiny nipples are finally visible. Her round belly hangs down too, but rather than appearing unattractive, it adds to her curvaceous sexuality. My fantasy image is made complete as I Bomonti Escort Bayan visualize him placing his penis in Jessica’s vagina, sliding it through the thick mat of hair that protects her opening. His hands caress her big butt as he thrusts into her, filling her with his semen.

This image, combined with knowing my sister was masturbating intensely in her bed next to mine, pushed me over the edge. I thought about her butt rising and lowering to meet her hand…and how erotic she must look from behind with the thick crevice of pubic hair separating her rounded cheeks. I pictured her breasts pressed against her mattress and my arousal heightened as I imagined her fingers bringing her to her own orgasm. My left hand gently touched my scrotum, and I moaned audibly as I thrust my penis powerfully into my hand and felt my climax build. A fraction of a second later my semen squirted all over my belly and my hand as I groaned uncontrollably.

I lay back in somewhat of a daze, feeling that familiar post-orgasm letdown begin to wash over me. Within less than a minute, I heard Jessica reach her own climax. There were no loud screams, no verbal fireworks like you see in adult movies…just the sound of her moaning rise slightly in volume and become constant until she too lay motionless.

We lay silently for several minutes until Jessica broke the ice. “Well, we both needed that I guess,” she said somewhat sheepishly.

“You got that right.” Always the conversationalist.

After a few more moments of slightly awkward silence, we started to talk for a while about other topics related to the wedding; in retrospect I sense that this was our way of proving to ourselves that we were still just a “normal” brother and sister, in spite of what had just transpired.

“Is it OK if I turn on the light and read for a little while?,” Jessica asked.

“Sure, fine with me…I’m not really ready to sleep yet anyway.”

I found myself unable to concentrate on reading or any other activity, and it must have become apparent to Jessica that I was either troubled or consumed with what had just taken place.

“Steve…are you OK with everything…I mean…you know, what happened? I mean, we’re still who we were before…and I just want you to be OK with it too.”

“Jess, you’re great, and I’m definitely OK with it too. It’s just kind of hard to put it out of my mind right now…but I’ll be fine.” Truth was, even though I had climaxed earlier, which usually precluded me from thinking about anything even remotely sexual for quite some time, I still had trouble shunting the experience aside.

Jessica, always in tune with the emotions of those around her, must have sensed my slight dishonesty. “Come on over here…I need a hug, and I think you do too.” I fleetingly thought about this invitation…where it could lead if by some odd chance it was anything more than a simple display of affection, and whether it was best to just leave things as they were and treasure the memory. But then again, I realized that knowing Jessica, she really did just want to hug and reassure both of us that nothing had really changed between us. Giving her outgoing nature the benefit of the doubt, I decided that a quick hug would go a long way toward cementing our newly formed bond.

I got up from my bed nervously, a sorry sight I’m sure. The light was still on and my tight pajama bottoms did little to conceal the tiny lump my flaccid penis formed, serving to clearly outline my bulge in all its miniscule glory.

Jessica motioned for me to lie down next to her; I was counting on a quick and innocent embrace, then a return to my own bed. Her covers were pushed down, and she lay on her side in her nightgown, which had bunched up highly enough to provide me with a view of her dark blue satin panties.

The sheet was unmistakably damp underneath her lower torso – obviously the result of her earlier orgasm – and as I climbed on top of her bed, her musky scent became inescapable. The combination of wetness and scent reminded me of my many masturbation sessions with Amy’s bra and panties…licking the inside of her bra cups where her nipples had lain while smelling and tasting her slight perspiration…doing the same with her panties and then thrusting my penis into them at the exact aromatic spot where her vagina had rested.

As I lay on my side next to Jessica, she put her arms around me and reassured me that everything would be OK, that she felt really close to me, and that we hadn’t really done anything wrong other than pleasuring ourselves to relieve our frustrations.

As wrong as this entire situation was, I felt a bonding with Jessica that I had never felt with anyone before, including Amy. This whole thing may have been inappropriate, but sometimes our society’s standards about what is correct just don’t apply to every situation. But alas, as with just about every relationship I’ve had, embarrassment was about to rear its ugly head again.

To Escort Bomonti my horror, I felt myself becoming erect, and there was no doubt Jessica could feel my penis against her…it was pressed against her lower abdomen near the top of her panties. Making matters worse, I could see fully into the top of her nightgown…and my gaze was locked on her breasts. Jessica quickly realized both my arousal and where my eyes were focused. I instinctively pulled away several inches from Jessica in an attempt to regroup and try to make some sense of this all. Fortunately, once again, Jessica’s comfort level and fearlessness helped me to feel at ease.

She smiled. “Not much too look at, are they…especially compared to Amy’s.”

“Oh Jess…I’m sorry…I didn’t mean to…no, they’re beautiful.” Eloquent as always.

“Yeah, right,” she replied with a fair measure of doubt. “They’re small and they’re saggy. God, I wish I had nice boobs.”

But I found them incredibly sexy, even more so up-close than from a distance in the shower the previous day. Her breasts were a beautiful shade of off-white, and even though her nipples were still flush with her breasts, I could now see their outline against her aereolas. The dark hairs on each aereola were thicker and coarser than I had imagined, and I found them extremely sexy as well. I would never be so bold, but at that moment I wanted to move my head down and begin kissing her breasts, suckling them, licking her areolas, feeling her breast hairs in my mouth…demonstrating to Jessica just how sexy she was.

“Jess…they’re great, believe me,” I said. And I meant it with all my heart.

I finally forced my eyes away from her breasts and was shocked to see her looking directly at the front of my pajamas. Their tightness left nothing to the imagination as my penis stuck straight up toward my chest, creating less of a bulge than a slightly elongated rise that ended about an inch below the waistline. An erection of slightly more than four inches hardly creates an impressive sight.

“Your body’s nice, Steve. Amy’s lucky she has such a good looking husband. She then giggled as she looked at my erection and added, “And your thing is cute too.”

Cute. Great…she thinks it’s cute, which I guessed was her way of saying something nice about my obviously quite small erection.

“I know, I know…there’s not much there. But it’s all I’ve got.” I couldn’t believe I was discussing the size of my penis with my sister, of all people. At least it was nominally covered by my pajamas.

“I’m sure it’s plenty. Don’t underestimate yourself. Amy should be glad she’s got a great guy like you. She doesn’t know how lucky she really is.” Jessica then pulled me to her, resuming our earlier embrace. I felt scared and aroused at the same time.

Lying on our sides facing each other, we held each other closely. I could feel her warm breasts encased in her nightgown pressing against me, and I could feel my penis touching the front of her navy blue nylon panties, padded by her thick pubic hair. We just held each other tightly…the situation felt so wrong, but neither of us pulled away.

Not a word was said…speaking was unnecessary. Our heads rested next to each other on her pillow, and our bond reinforced how much we meant to each other, even absent any sexual influence.

My hands caressed her back gently, and she did likewise; her hands eventually moved down my back and lightly rested on my rear end. I can’t recall Amy ever touching my body in a loving way, and the sensation was intense. I felt briefly uneasy about Jessica’s touch, but this passed rapidly as I was enveloped in our embrace. Tentatively, I did the same, and when my hands came to rest on the fullness of her butt, I sensed I was losing control. The sensation of being this close to Jessica in this intimate a setting was too much. I tried desperately to think about anything non-sexual, but to no avail. I tightened as I felt my semen begin to flow…filling the front of my pajamas as I ejaculated. This had happened with my other partners too, and I knew that the wetness in the front of my pajamas would instantly give me away. I was at the height of embarrassment, knowing Jessica would realize within seconds that I had climaxed.



“It’s OK…calm down…it happens.

“God, how embarrassing. I’m sorry Jess…it just felt so good holding you.”

I pulled away from her, mortified at my ejaculation and not knowing what to do to get out of this humilifying situation. I looked down and saw that my pajamas around my now-soft penis were soaked and sticky with my semen, which had also transferred to her panties near the waistband. I also noticed a much bigger dark, wet area on her panties beginning near the juncture of her legs.

Jessica looked down also, and surveyed the situation. I didn’t know what to say, what to do, what to feel. Not only did she know about my non-existent sex life and my small penis, but now she knew about the premature ejaculation which was a constant plague.

“Hey, it’s nice to see that you liked hugging as much as I did,” Jess said gently. Guess you can see that I’m still turned on too,” she added, acknowledging the wetness her own secretions had created on her panties.

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