Playing with Tilly

Sarah going to spend Time with Jim had become expected but it was still exciting, even Tilly seemed to enjoy it. For Tilly it was different. Tilly understood that Sarah wasn't truly hers. She knew that she ranked below Jim on a physical level and below Tom on an emotional one so while she was enjoying being a part of this unusual relationship she hadn't developed any jealousy. It didn't feel like she was being cheated on because that wasn't her place in this weird love square head had become part of. Meeting Sarah had exposed her to Tom and his kinky fetish and she was really enjoying being a part of that. She had also developed a soft spot for him. She wasn't in love with him or anything but he had welcomed her into his home, made her feel very welcome and playing with him was a lot of fun.

She had started to look forward to Sarah spending time with her lover because she could enjoy some time with Tom just hanging out and teasing him in her own way. In another world she would have quite liked him to help her understand her bisexual side but now he had lost his cock all together she found it hard to picture him as much of a man any more. She had discussed it in bed with Sarah the previous night as they lay in bed together. She had laughed "You should probably tell him, he'd probably get off on the idea he might have had a chance to have sex with you but you changed your mind."

Tilly had laughed in return "Yes, I guess it's kind of his thing isn't it. I really like toying with him now. It makes him kind of feminine."

"Feel free to tell him that too. I really did marry an emotional masochist."

This had made Tilly think. She didn't want to discuss it with Sarah partially because she wasn't sure if she'd go for it and partially because she wanted to keep it for herself, for now at least. Still, she had him to herself tonight and depending on how things went she would try and get him to do what she wanted.

Things went as they usually did. Dinner followed by hanging out on the sofa watching something that one of them wanted to introduce to the other. She was sitting there trying to think about how to turn the vibe sexy when she received a gift from fate. Tom's phone buzzed and it was a photo from Sarah. It was a selfie of her holding Jim's cock next to her face. The caption read: So lucky to have such a big beautiful cock to satisfy me #blessed. Tom showed it to Tilly and she had to admit that she felt a little pan of jealousy, not of Jim but of Sarah. She found herself looking at it quite intensely before Tom asked for it back. He looked at the picture again and squirmed in his seat.

Tilly leaned forward and said quietly in his ear "Struggling?"

She made him jump a little and he looked over a little embarrassed "Yea" he confessed.

"Want to fool around a little? If you are a good boy and do as I say I might help you out" she said wiggling her finger teasingly at him.

He was ashamed at how much he wanted to take her up on her offer. His heightened libido meant that only a day without cumming felt like he hadn't in at least a week and the inability to stimulate himself meant his arousal just kept building and took a long time to dissipate. Also he hadn't yet braved taking matters into his own hands meaning Tilly was the only way he knew he could orgasm. So it was with a bright red face he said "I'd like that."

Gleefully Tilly flung her leg over him and sat on his lap and began pulling off his t-shirt. Once she had flung it off him she grabbed his face and started to kiss him. Tom was surprised by the gesture. Tilly had kissed him before but always with Sarah there and always once proceedings were well under way, this felt very intimate and he gently pried her off him "Tilly, I'm not sure we are supposed to be kissing like this."

Tilly shrugged "Maybe when you and I could still fuck but now Sarah isn't worried about it. I asked her and she just said to go for it because it will only work you up more. Besides" she added "I like kissing you" and without giving him opportunity to respond she went right back to kissing him.

Tom decided not to look a gift horse in the mouth and continued to make out with Tilly. His wife had been right about one thing, it was winding him up. He put his hand on Tilly's slender waist and slid it up to caress her breast. Tilly took his wrists and pinned them to the back of the sofa "Ah, ah , ah" she said "No touchy, be a good boy or miss finger wont pay a visit to prostate town."

It was clear that he should let her lead and not try to initiate anything and he was quite eager for her to do that thing she did so he behaved. He couldn't really complain, it was pretty luxurious as Tilly ran her hands over his hairless body. She kissed down his neck and chest and sucked on his nipples squeezing and lightly pinching them like they were breasts. Nobody had ever done that to him before and with his missing penis he found that the pleasurable stimulation was invigorating and he found himself gasping and moaning as Tilly worked on his chest.

Tilly lifted her head and started working at his trousers "I love hearing you moan, it's so sexy. Lift your bum" she added as she pulled down his trousers and underwear in a smooth motion and hauled them off his legs leaving him naked. Tilly just stood there looking at him and he felt very **** his cheeks flushing with colour. "Hmm," she mused "I can't see you properly, stand up" she ordered.

Tom wasn't sure what her game was but he did as she wanted. "Legs apart a bit" she said walking sexily up to him. He shuffled his feet apart and he could feel the air tickling the area where his cock and balls should be. "I love it" she said pressing herself against him "It's so smooth and sexy and alien." She slid her hand between his legs and ran her fingers over his featureless crotch "If you had a pussy I could be fingering you right now. You'd love it, I'm very good." She reached underneath him and slid her fingers against the crack of his behind "You want me in here don't you?" she asked with a knowing smile.

Shakily and quietly Tom said "Yes."

Tilly straightened up and pulled his head down close to her "Say it. Tell me what you want me to do."

"I, I want you to, to..." he swallowed hard.

"Go on"

"I want you to finger my ass."

"Good boy" said Tilly and kissed him "But not right now. I have something I want you to do for me first, wait here." Tilly kissed him briefly then dashed out of the room and ran upstairs. He could hear her moving around up there but had no idea what she was doing. Eventually he heard her thunder down stairs and bust back into the living room with what seemed to be clothes.

"Tilly, what are you doing?" he asked wearily.

"I want to play dress up" she replied excitedly.

"Tilly, no" he moaned "I don't want to wear women's clothes."

Tilly pouted "Aww, I really want to dress you up. I know, if you put these on I'll take my things off" she said swaying her hips and running her hand down her body. "And besides I might not be in the mood to get you off if you don't" she added with a grin. She knew he was horny "Come on, what's the harm? It's just a bit of fun, humour me, please."

Tilly was giving him puppy eyes while swinging her hips slowly side to side "Fine, what do you want me to wear?"

Tilly jumped and clapped with excitement and threw him something tiny and black which he caught. Upon examination it was a small lacy black thong. He sighed "I might have guessed" he said resolutely as he worked out how they should go, slipped his feet into them and pulled them up. The material felt alien on his smooth legs and he winced slightly as the fabric slipped between his bum cheeks and the lacy fabric sat snugly where he should have had genitals. He couldn't help but run his hand over the fabric and marvelled at how it felt to different to his fingers as it would if he was touching a woman. He had to admit that in his present state they weren't exactly uncomfortable.

Tilly made a noise "That looks just as sexy as I thought it would" she said "Turn around, I want to see the back." Tom obliged her "Hmm, a bit disappointing. You have such a man's bottom. I hoped it would look cooler. Anyway, next item."

"Hang on, you need to take something off"

"I'm not wearing much. You have more to put on than I have to take off. Sit down. I'll probably have to help you with this bit."

Tom perched on the edge of the seat as Tilly approached him with what looked like tights but turned out to be stockings. She rolled them up and held open the elasticated top as Tom slipped his feet into them and she rolled them up. When done she straddled his legs and lifted off her top to reveal her bare breasts. She playfully brushed his face with them before going to get the next item. He suddenly was starting to enjoy himself a bit more.

The next item was a dress "It's pretty stretchy so even if it doesn't fit perfectly at least we won't ruin it" said Tilly. Tom tried to slip it over his feet like a pair of trousers but couldn't work out the best way. Tilly laughed at his confusion and pulled the dress over his head, guiding his arms out of the sides and pulling his head through the neck hole. The dress clung tightly to him. It was black with a slight shimmer to it. The neckline was high, right up to his throat but the hemline was also high and with his height being much greater than either Tilly or Sarah it failed to quite cover his panties leaving the bare top of his thighs visible. His arms were completely bare.

Tilly looked extremely pleased with herself "I mean you totally look like a dude in drag but I dig it. I wish we had some heels but nothing we had would fit you. Oh yea." Tilly remembered the deal and whipped off her shorts and panties. She picked up the panties and handed them to Tom "Feel how wet they are? That's the effect this little game is having on me." She stood back and picked up her phone "Come on now, strike a pose."

Tom looked shocked "No, you can't take pictures" he protested.

"Why not?"

"Because someone might see them" he insisted.

"Well I was going to show Sarah. Come on, I think she'd like to see. Who else am I going to show it to? Nothing's going to happen."

Tom relented but looked awkward "What am I supposed to do?" he asked.

"Just put your hands on your hips and smile. Try and look feminine."

After a lot of laughter from Tilly and some pointers he finally made a pose she was happy with and she snapped a few pictures. She put the phone down and walked up to him. Despite the difference in their heights Tom felt a little intimidated as she grabbed his butt and pulled him towards her "I want you to climb on the couch on your hands and knees and stick your ass up. It's time to reward you for being a good girl."

Tom ignored the girl comment. It's not like he had much room to argue dressed as he was and he was more than ready. Being dominated by this slip of a girl was pushing all kinds of buttons. As he turned she slapped his behind and whistled as he crawled onto the sofa his behind almost exposed because of the shortness of the dress. Tilly came up behind him and rubbed his back before sliding her hands down and lifting up the hem of the dress fully exposing his thong clad bottom.

"My, what pretty panties you have on" she teased "I'm going to leave those on I think." A moment later Tom felt Tilly's hands pulling aside the thong and her breath on his buttocks quickly followed by the increasingly familiar feeling of her tongue on his anus. After a little probing she said "Mmm, you are getting used to this, I can feel you opening up for me. Are you so keen to get me inside you?" Tom didn't answer but Tilly wasn't expecting one as she slipped a finger inside him.

He gasped at the invasion and was mortified at how much he had been longing for it. As Tilly worked her magic he found himself twisting his hips to try and increase the stimulation. Tilly laughed "I think you want more. Maybe I should add another finger, what do you say?"

"Yes" she said almost imperceptibly.

"I'm sorry?"

"Yes" louder this time.

"I'm afraid I need you to be specific, yes what?"

"Yes, please put another finger in" he said with frustration.

"Oh you can do better than that. Beg me a little at least."

"Please Tilly, please put another finger in my ass, I need to feel it."

"That was perfect" she said as she slipped the second digit into him casing him to moan.

She fucked him like that for a while, wiggling her fingers in the ways that got the best responses from him. She was pleased as punch when he called out "Right there, don't stop" and a moment later she could feel him twitching inside as he ruined the black panties with cum.

Tilly tutted bus didn't take her fingers out. She continued to stroke him slowly as she spoke "You made a mess of those lovely panties I gave you. You should apologise."

"I'm sorry" Tom groaned in a daze.

"Well I guess I could forgive you if you promise to wear some more in bed tonight and all tomorrow."

"Really?" he began to protest but Tilly pushed hard on his prostate "Ah, okay, I'll do do it, just let me rest."

"Good girl" said Tilly slipping her fingers out of him. "You go and clean up and I'll find you something to wear."