A Bad Bet with a Playful T-girl

"Mhmm," he purred dreamily as Beth rolled it on.

Beth smeared some glue onto his chest and turned away to retrieve something just out of sight. Coming back to place two D-cup breast forms onto him.

"Hold them there Jackie. That's great. It'll take a little time for the adhesive to dry so while you're doing that I'll put your makeup on."

"Glued breasts and makeup? Is this not a little bit too..."

"Hush sweetie, they won't fix properly if you keep talking."

He frowned but closed his mouth, wondering how much difference it could possibly make. Maybe the extra vibrations from speaking would cause the boobs to shift. He tried to maintain shallow rhythmic breaths.

Beth suppressed a smirk. He could be so gullible sometimes. She just needed to concentrate on his makeup and didn't want to hear any more protests or have to answer any more silly questions.

She expertly applied her skills. Starting with the mascara and eyeshadow before swiftly moving onto the foundation, concealer and blush. Once she was happy she picked out the perfect shade of red for the lipstick and applied the finishing touches. Beth stepped back to admire her work. Very cute, very feminine and very, very sexy. It took all her willpower not to just jump him right there.

"OK hands away, let's see how they've set." She gave them a little testing squeeze. "Ooo perfect. I hope you like them, they're high quality boobies and they even have a non-membrane skin so you can sleep in them. They were mine before I got the real deal."

She quickly set to work blending in the edges of his breast forms with makeup.

"Kaan I twwk nww?"

"What? Oh can you talk now! No, not until I finish. Now stand up so I can put this on you. I know you'll love it as much as I do. It's the floral lace bustier that goes with your stockings and thong."

Beth stood back to look at her creation and let out a low level primal growl, before shaking herself back under control as they both blushed and looked away. Even without the wig 'Jackie' had taken shape very nicely in the white virginal lingerie. It was time to complete the sweet innocent look she was going for so she could introduce her new 'girlfriend' to their friends. Beth was excitedly looking forward to all the fun of showing Jackie off to them and hanging out together. The fact that she would get to deflower the beauty she had created afterwards was just the icing on the cake.

"And now a nice summer dress. Come on, arms up..." It slipped into place and she smoothed it down with her hands, allowing one to linger on the hardness that signalled just how much he was enjoying the experience. She gave it an appreciative little squeeze before moving on. "And finally your wig."

She fixed and brushed out the auburn wig, turning his head from side to side to see if anything looked out of place. "Perfect," she cooed, giving him a peck on the lips, "Now go and have a look in the mirror," she said excitedly.

Walking to the mirror he studied his reflection carefully, practising some different looks, from coy glances to seductive smiles. He could still see himself in the reflection but only just. Beth moved up behind him to wrap him in her arms. Kissing his neck while her hands roamed his body one squeezing his new tits as the other drifted down to take his manhood.

"Mmm you look divine, baby. I'm going to fuck you so hard later. I'm going to bend you over, hitch that dress of yours and turn that sweet innocent girl you see in the mirror into a real woman. I'm never going to let you go. Mmm I can feel you grinding back into me, you horny little thing. You're as desperate for this as I am." Again she kissed his neck, causing him to moan sweetly. "But that will all have to happen later. First I want to take care of you." She stroked him through the dress. "After all, we can't have this thing ruining the outline of that pretty dress can we?"

"No we can't. And as you're the one who made me stand to attention like this, it's only fair that you help me out."

"Oh really... and what are you going to do for me if I do assist you down there," she replied coyly, eager to see what extra concessions she could wring out of this.

"Oh I think I've done more than enough already Beth," Jack retorted, turning around and putting his hands on her shoulders. "But if you want more then how about I feed you something nice and creamy." The pressure on Beth's shoulders increased. "On your knees. If you're going to be my lesbian lover then you'll need to show me you can use that sweet mouth and dexterous tongue of yours for more than just talking and teasing."

Beth sunk to the floor and gave a mock, playful, glare. She had been hoping to get him to agree to a whole raft of fun activities before she wound up down here but actually this was better. She was dominant but she liked the push back, it made it more fun and this was more like the old friend she had grown to love. What could she say, she was a greedy girl. She wanted it all. The friend, the lover and the kinky human sex toy.

"Well that's not a very nice look is it Bethany," Jack smirked, "I think you'll look far better when you have my cock in your mouth but first..." He reached over and grabbed the lipstick from the dresser and handed it down to her. "I prefer lipstick lesbians."

She giggled and lightly shook her head before putting it on, rubbing her lips together and giving him a couple of air kisses.

"Is that better my love?"

"Much better."

"Well I should get to work then. This lovely cock won't just suck itself now will it."

Smiling, she raised the hem of the dress, reaching in to pull out his dick and tucking the fabric behind it like a peg. A rock hard cock in a frock definitely had its advantages when a girl wanted to keep her hands free for more... interesting activities.

Moving her head in she looked up into his eyes, mouth slightly ajar and paused. The cocky look on his face had dropped to be replaced with a look of desire and anticipation that was bordering on desperation. Good. She couldn't allow her girlfriends and boytoys to have too much power. After making him suffer for a little bit longer she winked and while maintaining eye contact pressed her tongue to his balls before slowly running it all the way up his length.

"Oh that feels so good Beth," he moaned as his legs shook.

"Mmm this is a really tasty cock you have here. And it's a perfect size for me to do this."

She plunged down to engulf the whole thing, taking it deep into her throat and holding herself down as his legs wobbled even more. Despite what she'd said this was at the very edge of her tolerance and she struggled to hold on without any warm up. But this was Jack, Jackie, her great love and she wanted to impress him. She convulsed around him as he moaned, pushing down harder to reach the last centimetre before pulling off and coughing.

"Hey are you alright! Your eyes are watering."

"I'm," 'aha' 'aha', she coughed, "I'm fine," she spluttered. "You," 'aha', "You're a little too big for that after all," she grinned up at him through the tears.

"Well you don't need to, you can take it a bit slower."

"Hell no!" She cried, wiping away the moisture from her eyes. "I've waiting for years to taste this beautiful fucking dick of yours and I'm taking it all and I'm taking it now!"

She dived back down, this time with her throat already opened up and more relaxed she was able to sink quickly to the base, fighting off her gag reflex and humming. The sudden vibrations caused him to lean back against the dresser table for support. She smirked up at him around his dick as she continued for another minute. Fuck yeah, that's the response I wanted, she cried out in her own mind and began to bob furiously up and down. Grabbing air when she could as she did her best to suck the life out of him.

"Oh wow Bethhhh, oh shit, Ohhhh I'm not going to last long if you keep it up like that."

It was becoming harder and harder to support his own body mass and he clung to the desk to avoid sinking towards the floor. Beth knew where this was headed but didn't want it to end too soon. Pulling off his cock she dragged his head down for a kiss.

Jack let her kiss him, enjoying her tongue exploring his mouth and she once again gripped him to ease the tension in his loins. He detected a certain taste, something vaguely familiar from earlier, but what? Dick. That was it. Last time it was hers but now he realised he could taste himself in her kiss and for some reason it excited him. Reminding him of all she had to offer when he returned the favour. She pulled away.

"Much as I love your lips there's something else desperate for my attention."

This time she was slower, dragging her tongue up and down his member before lapping around his glans and dropping down to suck on his balls. Slow, sensual and deliberate in every movement. Making sure to give him enough to stimulate and arouse but not quite enough to push him over the edge. Before long he was trying to push himself into her mouth but each time she either rocked backwards or used her hands to prevent him building to the intensity he needed.

She wanted him to be desperate.

And now he was.

Looking around she spotted her handbag and inched her hand towards it while still controlling his pace. Hooking it in her fingers she dragged it back to her and reached inside.

Jack relaxed into her ministrations, so good and yet agonisingly too little, he needed more, he needed to ask her for more. At the very edge of his perception he detected a barely audible 'pop' but instantly dismissed it as irrelevant. Beth grinned and coated her fingers before moving them into position. She was going to make him 'pop' very soon but she would do it on her terms. He'd still needed to ask her though. She'd allow Jack a bit more leeway but a good little girl like Jackie would need to ask before cumming.

"B.. Beth. Please I... I need more," he cried out, delighting her with both the desire and femininity in his voice.

"Mhmm," she cooed softly. 'Gotcha,' she thought.

Pulling the lacy strip of material to the side to expose him she moved her fingers into place. 'I'm gonna give him all the extra stimulation he can handle.'

As soon as her lubed fingers touched his ring he knew what was going to happen and he moaned encouragingly, instantly welcoming it. Beth circled her fingers around his twitching hole, tickling it before applying a light pressure at the very tip of her finger, slightly opening him up as he hummed appreciatively. Matching the movements of her digits to the tempo of her mouth and tongue as she continued to work. He tried to press onto her and she withdrew, grinning as she let him slip from her mouth.

"Do you like me playing with your ass baby, do you want more?"

"Yesss Beth, please keep going, I need more."

"Really? And what do you want me to do to you my darling?"

"I need you to finger me like you did at the party, please finger me."

"Ooo I'd love to honey but I only play like that with good girls. Are you going to be my good little girl? Are you going to let me play with you tonight? Let me play with this..." she dipped her finger inside him and tapped at his prostate before pulling back out again."

"Ooooooh wow. Oh yesss. Oh yes please Beth. I'll be your good girl, I'll always be your good girl, your devoted little Jackie."

"A good girl would let me slide my cock deep inside here." Again her finger slipped into his depths to rub against his prostate. "Will you let me do that to you?"

"Yesss I'd love that. I'll bend over for you, spread myself wide, let you take me anyway you want to me, but please. Please make me cum. I... Oooooooh yess thank you," he moaned as Beth finally relented and lowered her head to suck him back inside.

Almost there baby, she sang in her mind, almost ready for tonight when I properly break you in, when I truly make you mine.

She increased the pace ever so slightly, adding a second finger to tease away inside him as she slowly bobbed up and down. Moving him closer to the brink. With her spare hand she reached back into her bag for the final item she needed and deftly coated it. Now everything was ready.

She pulled her fingers from his hole and he looked down questioningly. She smiled up at him around his cock and pressed the very tip of the rounded five inch butt plug against his tight pucker. His eyes turned from disappointment to surprise. Beth winked and began to press it home, matching her movements to the plug, sliding the first inch into him as she took an inch of his cock into her mouth. She withdrew before going in an inch and a half, again with both her mouth and the plug, syncing the pace as she worked away.

Gradually she increased the depth, making him moan but never giving him more than he could handle. The timing had to be perfect. Before long she was really fucking him with the plug and sucking furiously. He was almost there, his knees were trembling, it was time.

With one final push she forced the plug home, stretching his hole wide before it popped into position and pressed hard against his prostate. At the same she dove all the way down to the root, planting her lips against his balls as he filled her throat.

In sensory overload Jack clenched around the base of his new toy and gripped Beth's head as he unloaded straight into her waiting stomach. Balls deep she watched him from her knees. She gulped down his seed, studying his enraptured face as he moaned incoherently. After all that edging his release seemed to have taken a lifetime to come and the length of his orgasm seemed to match. A full minute of burning, knee trembling intensity before it began to ease.

As his flow ebbed away so did his strength and he released the grip on his girlfriend's head. Pulling back she nursed the final spurts from her man, her girlfriend, her everything and swallowed almost all of it down. Almost. She'd saved a last little drop for someone special.

Pulling the thong back into place over his plug she rose shakily to her feet and kissed him. He relaxed into it before his eyes widened as she deposited the little part of his 'gift' to her into his mouth. As he held it in his mouth unsure of what to do her eyes hardened, giving him a single wordless command. Swallow. Beth smiled and her eyes softened as he gulped it down. She relaxed and kissed him tenderly.

"Good girl," she cooed, hugging him warmly. Jack needed to get used to the taste of cum, either as her boyfriend or girlfriend Beth was going to be feeding him her creamy loads every day from now on.

Leading him over to the bed she sat him down and brushed the hair from his eyes. Giving him one last kiss on the lips while crouching in front of him.

"Are you OK Sweetie?" She asked the question happily but with a genuine concern for his well being too. She'd been pushing him quite hard today.

"Yes. Yes, I think so." He moved and winced as the butt plug shifted inside him. "The umm... does this really need to stay inside me?" He questioned, already knowing her answer.

"Yes honey, you need to be ready for me tonight. Is... Is that going to be OK?" After a brief pause he replied with a light nod and she wrapped her arms around him. "Thank you my love, that makes me so happy." She gave him one last peck on the check before releasing him and standing up.

"You just rest up for a minute Jacks so I can get ready too. I'm not going to be walking around naked all day no matter how much you might like it. Not with Alice and Tom here anyway. I'm not into exhibitionism." She cocked her head to the side for a moment.

"Unlike Alice," she continued, "Alice is disturbingly into PDA. You know what that is right? She loves to put on a bit of a show and likes watching other couples if you know what I mean. Most of the girls in our support group were just normal regular girls but Alice is a hell of a lot kinkier than you'd think. She really likes you Jacks and always has but kept that wilder side of hers toned down around you in the past. She'll now be thinking of you as one of us so she might be a little bit more... how can I put this? Open? Playful? I don't know... in your face maybe. Just... don't take her too seriously, OK?"

She looked around to see him passed out and shrugged. Meh, he'd find out for himself soon enough.

**********

"I'm finally ready Jacks," she called out, doing a twirl. "What do you think?"

He wrapped his arms around her waist and pulled her in for a kiss. "As gorgeous as always Beth."

"Aww thanks babe, now let's go and see the others, I can't wait to show them the new you."

"I still don't know what was wrong with the old me."

"Nothing baby, you look great as a guy and I love you that way. But this week I want you all soft and feminine. And if you do what your girlfriend wants she'll reward you. You do want your girlfriend's thick creamy reward don't you."

"Well..."

"Yeah, that's what I thought. Come on."

Beth grabbed Jack's hand and led him through to where their friends were sitting.

"So what do you think of my new girlfriend?"

"Jack, is that really you?" Alice cried out jumping to her feet, "It is! Oh my god Beth I can't believe you actually got him to do it. Aww and he's turning all red and shy now. Aww isn't he precious."

"She! Alice. She! And it's Jackie when 'she's' dressed so play nice," Beth told her, clearly agitated.

"Uh-huh," Alice replied, waving her hand dismissively as she walked up for a closer inspection. "Oh no way! You shaved him too. Fuuuccckkk! I can't believe he let you do that to him!"

"OK, I think I'll go and get changed," Jack mumbled.

"What No! Damn it Alice," Beth shouted and stomped in frustration, "I'd have thought anyone who'd been through what we've been through would be a tad more sensitive."

Alice met her furious gaze and the colour drained from her cheeks as she realised how serious her friend was about this.

"I'm sorry I... I thought this was all just a bit of fun. Just a sex game."

"Yeah well, maybe it is and maybe it isn't." She said, resting a comforting hand on Jack's uneasy shoulders. "For years I've seen this other side to Jack that I knew he'd like to explore. The little things. Like how whenever I joked about dressing him up he was always just slightly too keen to keep it going, how he always had that little gleam of excitement in his eye. Well I've finally teased Jackie out of him and whether that's full time, part time or a one off peek-a-boo I don't want you scaring her away!"

A reticent Alice took Jack's hands. "I'm sorry Jackie, it was just the shock of seeing you like this. I didn't mean to sound like I was mocking you." She looked him up and down and bit her lip. Even through the makeup she could see him blushing furiously. "You do look really good though, very pretty, very sexy. You're a real cutie and I certainly wouldn't say no if I was single."

"Yeah OK, thanks but umm... despite what Beth might say I don't actually want to be a woman. You know that right?"

Alice looked into his eyes and smiled, Beth was right, there was something there, a little sparkle in his eyes when she told him that 'she looked pretty'.

"Well there's no rush to make any decisions babe. If you want to dress as an occasional kink none of us will think any less of you and if you ever wanted to do more we'd all support you. You're among friends so you just relax and have fun this week and we'll see how it goes. Oh and I'll try to be nice but I can't promise not to have a giggle at your expense."

"Ha. Well you wouldn't be you if you didn't," he grinned. "And you can laugh all you like bitch. We all know you're just worried about the competition."

"Yeah you got me. Tom's eyes were popping out of their sockets when he saw you come in so I'm just fighting for my man. If this hot piece of ass standing in front of you didn't keep him on a tight leash he'd be all over you. I'll let you into a little secret. Despite being mainly a bottom I'm still the dominant one in our relationship."