Dressing with the Captain
Publish Date: Sep 11, 2008
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That evening, I arrived at the Town Hall as arranged. I waited for David but he didn’t show up. It was nearly 45 minutes after the arranged time and I was about to give up when Captain Pockett arrived. I explained that David had not turned up and he said he’d begun to get worried because we hadn’t arrived. “Well, since David doesn’t look like he can’t make it, why don’t you come along anyway?”, he said. I felt a bit uneasy but agreed and we made our way to the Captain’s house nearby.
When we arrived, I mentioned that I used to have a great-great-aunt who lived just around the corner and that it was always said that only wealthy people lived in the area. “That used to be true”, he said, “These are big houses. Come on, let me show you around”. We went from room to room and, compared to where I lived, it certainly was spacious. The Captain pointed out photographs of himself and his late wife – some of them from their time abroad. “I miss her.”, he said, “Sometimes it gets very lonely.”
We went upstairs and looked in the bedrooms, most of which were unused, since the Captain lived on his own. In one room, however, as we were looking at some memorabilia, the Captain opened a wardrobe and said, “I’ve still got all my wife’s clothes – coats, dresses, underwear …” I gulped and, without realising what I was saying, said, “Do you ever wear them?”
I was immediately embarrassed, having blatantly exposed my obsession with women’s clothes, developed in my childhood through frequent glimpses up my grandmother’s dress and rather less frequent incidents with the various girls in the neighbourhood as we played as children. To my astonishment, the Captain calmly replied, “Yes, sometimes. Would you like to try something on?” “Well … erm …uh …”, I stumbled. “Oh, don’t be shy!”, said the Captain, “There’s nothing unusual about a boy wanting to put on women’s clothes. Almost every boy would, given the chance.” So I said, “Well, OK then”.
“Now, what would you particularly like?”, he asked. “Umm … I really like stocking, girdles and petticoats”, I said. He said, “Aha! That’s easy. Come and choose what you want. I’m going to wear these – my favourites”. He picked up a small pile of lacy things kept separate from the rest. Cautiously, I sorted through the clothes and found a prettily patterned girdle, some dark seamed stockings, a pair of pink briefs and a pink half-slip with about two inches of lace around the hem. By this time, the Captain was half undressed and starting to put on a suspender belt. “Come on.”, he said, “No need to be shy!” So I got out of my things and into the clothes I’d selected. It felt wonderful! I forgot my embarrassment easily as I pulled the sheer nylon stockings up my legs and hung them on the suspenders of the girdle.
We were both dressed in women’s underwear and it was obvious that both of us were straining to stay contained inside our knickers. I looked at the Captain and he said, “Well, it’s no good being shy now. We both know you want to wank – and so do I. So, let’s do it.” He slipped his cock out from under the leg of his knickers. It was a fair old boner – not huge – but respectable. He started to stroke it slowly and soon I had my cock in my hand and was doing the same.
Still wanking, the Captain made his way over to the bed and lay down. I walked across the room and lay down on the bed next to him. As we wanked, we talked about the feel of the underwear. He said he always enjoyed feeling the gusset pulling tight against him – his balls where his wife’s cunt used to be. I only had the vaguest notion of what that really meant but it got me even harder. Then he asked if I’d ever had any kind of sex and I said that I hadn’t, apart from the odd fumble with a couple of girls and the usual wanking with a couple of boys over some magazine pictures. “Then let me give you an idea what it’s like to put your cock into a woman’s cunt.”, he said. With that, he took my cock in his mouth, flicking his tongue over the tip and slobbering over the bulb. I was so overcome by the sensation that I lost track of what was happening. The next thing I remember was the tip of my cock feeling like it was on fire and rope after rope of my spunk jetting into the Captain’s mouth. He swallowed it all and then asked me to finish him off. Dizzily, I wanked him until he too shot his load.
I didn’t say much to David the next day. He explained that he couldn’t come out the previous evening. I said I didn’t mind. Eventually, we did all three get together at the Captain’s house one evening – but that’s another story.
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