
Transgressive Thursday
A Lad’s Dilemma: Dil-do or Don’t
After a few cans, we started playing truth or dare, and that’s when I told them about the toys I buy
“I buy sex toys.” I made the statement clearly and sat waiting as I knew the questions would come…
Jim’s parents were away for the weekend and the gang —Jim, me, Sid and Carl — were having a boy's night. No girls allowed. After a few cans and a Chinese takeaway, we started playing truth or dare, and that’s when I told them about the toys I buy.
“Sex toys? What do you mean, Mike? Like giant dildos and stuff?” Jim joked.
At that remark, Carl and Jim fell about the floor laughing.
I grinned, “What would I do with a dildo? I don’t fancy shoving one of those up my ass. No… I buy men’s sex toys, such as masturbators. It just adds a bit of variety instead of my hand.”
“Why do you need it though, Mike? Come on, with a chick like Tessa on your arm and in your trousers.” Carl asked.
“How old are we? It’s not a trick question. We’re only eighteen and I don’t know about you, but sometimes ‘ol Dick’ can be a little fast out the trap, when Tess is around.” I was being real.
Well. They do say honesty is the best policy. This one admission of mine started a whole discussion. Testosterone filled the room that night, as we swapped embarrassing or humorous tales about being a little premature when having to deal with hot tottie.
Carl’s girl has got it all going on. Big tits, round arse and a face to launch a ship or two. He explained how the second time he took her on a date to the cinema, she let him put his hand down her panties. When he felt her plump, wet slit, his balls couldn’t hold it in. He exploded in his boxers right there and then. After the movie, he buttoned up his coat, hiding the misdemeanour, and said goodbye to his girlfriend in double quick time.
As soon as Jim had managed to stop laughing, he went on to tell how he would run down the previous weekend’s football results in his head while shagging Gill. Just so he could fuck her for longer and give the impression he was a stud rather than a newly-released virgin.
“Right guys. Now you know why I buy them. I never take my bird out without having taken the toy for a whirl first. Then, I can at least make it to 10pm before the sight of Tess gives me a raging hard on.”
Jim started up his laptop and got straight down to the business of checking out a few sites, and finally selected a Penis Sleeve. He turned to Sid and asked, “You want to take a look before I shut down the computer?”
Sid had been quiet up until now. But he didn’t have a girl. Never had. We all turned and looked at him. He pursed his lips and as quick as a flash, his face turned a bright beetroot colour.
“Hey mate, what’s wrong? Com’on, we are getting down and truthful tonight. Tell us anything.” I encouraged.
He looked like he was going to explode when finally his mouth burst open, he took in a much-needed breath, and exclaimed,
“The thing is — I DO want to shove a dildo up my ass!”
For a moment, the room went quiet until Carl failed to stifle a laugh.
Reassuringly, I put my arm around Sid’s shoulder and said, “Whatever floats your boat is OK with us…”
PS: FYI, he purchased a 13 inch, purple, double ended dildo, and they are very happy together.
Another Tale from May
And one by Rocky Shores
Transgress with us?






