Chapter 2

About a week later, Will told me that he’d heard back from both Jack and Richard. Richard was the Dad of teenagers and Jack was the older guy. Neither of them knew what to make about me going with him to meet them, but he showed me their emails, as well as the emails he’d sent to them. He hadn’t told them about the blow job I’d given him, but he had explained, fully and honestly, about getting caught wearing my things and how supportive I’d been of him. I told Will to give them my mobile phone number so that they could call me if they wanted.

Richard lived closest, whereas Jack would have quite a long journey to travel here. We agreed to meet up with Richard first and Jack a couple of weeks later. Jack suggested that he booked a hotel room so we’d meet him there. That seemed like a good idea, so we sounded Richard out on doing the same. In the end, Richard and I agreed to go halves on the room with him.

We booked a room at one of the large airport hotels, as we felt that there would be so many people coming in and out of the hotel at all hours and this would make us easily forgettable. On the day, I packed a suitcase with lots of my clothing, dresses, underwear, wigs, blouses and skiers, as well as some make-up. We took an uber to the hotel and I checked in. We always intended to be first at the hotel and we thought that Richard would come up to the room on arrival. But in fact, he was nervous to go to the room without seeing us first, so we agreed to meet him in the bar.

He was a well kept man in his late 40s. He had a tidy, short beard and he looked as if he kept himself trim. I liked the look of him and we went straight up to the room. He had brought a small bag of clothes with him, and this turned out to be underwear belonging to his wife and his daughter. There was a nice armchair in the corner of the room, and I ensconced myself there and relaxed with my tablet.

Richard and Will sat on the bed and quietly continued talking about the things they’d been talking about via email. Though I was browsing on my tablet, I could hear everything they were saying. Richard had worn his own mother’s clothing growing up, though that had cost him several spankings each time he’d been caught. He said he’d had a lifelong lust for women’s underwear and men who enjoy dressing as women. His wife had found some of her underwear in their son’s room and had confronted him, unwisely in Richard’s view. On the other hand, they’d never found anything like that in his room since then, so his wife thought that the intervention had been successful.

Richard said that he had masturbated to the thought of his son with his wife’s underwear and it had reawakened his own interest in playing with underwear, hence the ones he had brought with him. Will asked if he wanted to put some on now,, and Richard asked if that would be OK with me. I told him that if Will was happy then I was too. Both got undressed and I saw both of them hard, very erect, as they were undressing. Richard had a huge penis, at least two inches longer than Will. To start with, they both put on clothing that they had brought with them. Richard was wearing a purple thong belonging to his daughter and Will wore leopard skin print briefs I’d bought in a pack from Primark.

The two continued to chat but were now masturbating. Will ejaculated first and his cum landed on Richard, who returned the favour to Will a few strokes later. As both were recovering their potency, they changed underwear and Will chose a pair of Richard’s wife’s - a beige pair of waist high briefs. Richard wore a light blue french pair of mine and I confess to feeling a bit excited as I watched them. Will came easily again a second time but Richard was finding it harder to ejaculate so soon after the first time. He was nicely erect, but just going to take him a long time to cum.

I found I wasn’t looking secretly at the two any more; I was actively watching them both. I recognised the lust building up inside of me. Richard suggested that Will masturbate him, and that brought a huge smile to Will’s face. That cock must have felt very different to his own, so long and so thick. With Will wanking him, he came after a few minutes. It was obvious they both needed a little time to recover so I went down to the mini-shop in reception and picked up some pop, crisps and chocolate.

When I got back to the room, Will was in the toilet. Richard and I started chatting, and he said he couldn’t think of another Mum like me. I just told him that it would be easy to be close-minded, only saying no to things and punishing Will, rather than supporting him. He thought I’d make a wonderful wife, and I told him that a naughty Dad like him would match that wife, but I wasn’t looking for a relationship nor was I interested in breaking up other people’s marriage! At that point, Will came back. He was stark naked but fully erect.

“What do you want to wear now,” asked Richard. Will pointed to a pair of mine that I’d worn a couple of days before. They were jet black and lacey. He put them to his face and inhaled my scent from the gusset. “Worn ones? I should have brought some from my family! I often enjoy their aroma as I wank” “Try these then,” I said, and I undid my skirt, which fell to the floor and removed a coffee pair of briefs. I handed them to him, and he sniffed them, which brought my lust up even further.

He pulled on my warm knickers and his erection was pointing out from the top. I went back and sat down, naked from the waist. This time, Richard and Will both gently masturbated each other. They continued chatting, about panties, girls, his wife and daughter, and then Will asked whether Will ever thought about me. He blushed a little and mumbled.

“It’s fine. I often used to dream about my Mum,” he said. I looked over and Richard was looking straight at me. He caught my eye and winked. I winked back and smiled. He just raised his eyebrows in invitation, and I walked over to the bed and took off my top. I asked Will to remove my bra. I hadn’t planned this, not even in my most depraved midnight masturbating fantasies. But at that moment, I wanted Richard and I wanted to play with Will as I was fucking Richard. Richard was lying down and I just straddled his cock, and I did gasp as it entered me. I controlled the fuck, as I rode him. In the event, Will just pulled back and watched everything. Because this was going to be Richard’s third cum of the day, he lasted well and that gave me extra pleasure. In the end, I came after getting very nosey and finding a stream of cum from Will which landed on my tummy.

After that we all lay there for a while, till Richard said he had to go. I let him leave with the pair of panties I’d taken off. Will and I lay there, cuddling.