A boy who does as he's told

“Bend forward...” Came the instruction, which Jesse followed compliantly. He felt the steadying presence of a hand upon the small of his back. He thought it was the entrancing, tall and thin one who was dealing with him this time, but dare not turn round to check. He’d seen her or him take off those long, silk gloves in preparation for this task. Further along the line a surprised-sounding “Ooooh!” told him one of those he was going to be connected to had already had their turn. He felt the back of his skirt being lifted up and a cool presence introduced between his ass-cheeks. The squelch of a bottle told him some kind of a fluid was becoming involved, but he really had no experience on which to draw upon for this scenario. He understood that such things as ‘butt-plugs’ existed… but had never actually seen one in use. The objects strung up along those chains had appeared so big.

His mind trawled back through his very limited sexual experiences up to this point, **** for something else to focus on… but unable to detach from the avenue down which his worries escalated. Sharing a room with Betsy had meant his opportunities for… exploration had been limited. Sure, he could wait for her to fall asleep and then load up the glitchy, old flexitab that they shared… But the fear of her waking up, and then the couple of embarrassing times it had actually happened, made such forays a fretful and hurried affair. When she had caught him the third time… and then just wordlessly clambered in to bed next to him… it had been the most wonderful and horrifying night of his life. From then on, there had been an unspoken agreement that, at least one night a week, they would sit side by side half-naked and watch whatever colliding naked figures they could find on that small and flickering screen. Of course, he had let her do most of the selecting… more content to simply feel the moving muscles in her arm against his shoulder than to care much what others got up to. From there things had just escalated… all the way up to the adventures of the night before. As in all things, Jesse had just gone with the flow… hoping to keep a smile upon the faces of those he cared for.

An icy visitor was knocking upon his rear door. He could feel a drip of the viscous fluid it was drenched in, trickle off down his perineum. A steady, consistent pressure began to **** itself inside of him. He felt things stretching. Widening. Sending panicked signals up toward his brain as to what exactly was happening here.

“Just relax…” Said that soft voice, floating in the air above and behind him. The same voice which was pushing this invader further into what had only ever been an exit till now.

Yet, it did help him relax a little… Jesse was not unaware that he had always just found it easier to do as he was told. Whether that made him a ‘1st Class Sissy Slutwife’ or not, he wasn’t certain. But it did mean he wasn’t going to buckle or run away when someone was just, very gently, sliding something into his rectum. Once it was what felt like halfway in, the going became easier. The senior carefully rocked the thing forward and back, getting it just a little bit deeper every time. Jesse found he had a strangely intense ball of sensitivity, somewhere around there… which sent deep shivers of dark emotion through every pit of his being every time it was pressed upon. He shuddered a little to feel his small cock rising again as these sensations shook through him, but hardly felt it was the most embarrassing thing happening right now.

At last he felt himself closing up around a new weight he was entirely encasing. He could feel the cold lump of it pressing against the depths of him, and his legs shook as he stood back up and felt the chain attached to it tickle against his ass-cheeks.

“Good girl!” Announced that soft voice, full of genuine pride. Jesse turned to look over his shoulder at the beautiful face above… and was rewarded with a quick press of lips to his forehead. The soothing sense of their presence seeming to linger there for a long while afterwards. Waking up to the rest of the universe a little more, he heard a few light snickers from those around him. The girl to his right offered a warm, little wink… chained as they now were to each other by the same unorthodox circumstances. Looking around further, Jesse realised he had taken considerably longer than anyone else to envelop the metal plug… and the other seniors were already moving steadily down the lines, eliciting gasps and groans and squelches wherever they went.