Joan and her husband Tim always do something special for her birthday. He strives to treat her like a queen for the day and to make everything perfect. He believes that she deserves to be showered with love and of course, she’s not going to object to that sort of thing because she loves being pampered. Today Joan turns 34 and her husband has prepared a beautiful meal for her, or at least that’s what he said he was doing. They’re at the table drinking some wine and talking when he announces that he got her a very special gift.
“Honey, I thought long and hard about what to get you this year and I thought I would go in a direction I had never even considered before. I think you’ll enjoy it though.”
Standing up Tim said, “Honey, I’d like you to meet your birthday gift.”
The kitchen door swung open and a man in a thong, gloves and a cowboy hat walked in. His body was a work of art, like Michelangelo’s David but carved from an even harder stone. He was perfection from head to toe and Tim had spent quite a bit of time online looking at agencies that provide this sort of entertainment. He wanted to make sure that his lovely wife got the best for her birthday and from the looks of things he had done a very good job. The man’s name was Richard and he had plenty of experience entertaining couples but tonight was going to be unlike any other, as he would soon find out.
At first, Joan was taken aback. She and her husband had never talked about swinging or her cheating or anything like this. From the way Richard was dressed and the way his dick was already bulging she could tell that this wasn’t going to be a simple stripper to dance for her. He was clearly compensated to bring her more than just the titillating thrill of a lap dance or a cock brushing against her body.
“What is that monstrous thing between his legs Tim? Could that possibly be his dick?”
She was clearly preoccupied with his big cock but she didn’t think that she could even take it in her mouth, let alone her pussy. Looking at the tasty piece of man meat standing in her dining room an idea popped into Joan’s head. For years she had harboured the desire of seeing a man in women’s clothing and it seemed like this was the perfect time to make those fantasies come true. The beefcake was obviously well paid she assumed he would be willing to do anything she requested as long as he got his money and didn’t end up with any permanent marks on his body.
As it turns out she was right on the mark because he acquiesced kindly when she asked him “Richard, would you come to the bedroom with me and put on something sexy?”
“Sure thing, ma’am,” he said while tipping his hat in the cowboy style.
He didn’t know what she intended on him wearing at that point so the question was probably a little misleading but she still had a feeling there wouldn’t be a problem. She stepped into the doorway of the bedroom and noticed a hesitation in Richard’s step she unbuttoned her dress and let her enormous breasts slip out. His eyes immediately went large at the size of those grapefruit beauties the beautiful blonde had and he took it to mean that he would soon get to fuck her. After all, his dick was essentially what she had been given for her birthday. That’s not quite how things were going to go through.
Joan pushed the sliding door that guarded her clothes to the side and peered in at all her sexy lingerie, slinky clothing and slutty tops. She wanted something feminine and sexy for the male stripper and after a careful deliberation, she went with a sexy blue satin slip that she thought would look perfect on him. The light colour would soften his hard muscles and his carved face. The site of him becoming a crossdresser right in front of her eyes was pretty powerful and as it turns out it was even more arousing for her husband.
Joan hadn’t really considered what she would do after she got Richard to wear her clothing. Luckily for her nature took its course and set the wheels of arousal in motion in the house. By the time she dropped the sexy satin slip over his head, she knew that he needed makeup. The first thing would be some dark red lipstick to make him look like a cocksucker. Then she would apply a little bit of foundation to cover up his rugged, manly skin and his little bit of stubble. Some eye shadow and a little bit of blush would be the final touch and just like that, he was feminine. He was becoming a sissy boy without much effort; imagine what she could do with him if she had all the time in the world.
Tim was hard after Richard put the satin sissy slip on and by the time he was all made up and sexy looking Joan’s husband could barely keep his erection under control. Much to his lovely wife’s surprise, Tim needed to fuck and it wasn’t her pussy that he wanted to stick his dick into. Instead, he wanted to fuck the new forced crossdresser in their house and he wanted to fuck him hard.
Despite all of Richard’s experience stripping for and entertaining couples, he had never done anything like this. He had fucked plenty of sexually frustrated wives but he had certainly never been fucked by a horny husband who got off on seeing another man in lingerie. But by the time Tim had him bent over and was forcing his cock into Richard’s tight virgin asshole there was very little he could do. His choices were to make a big stink and walk out without getting paid or simply bend over, take it and see how the night evolved after his newly sissified ass was fucked.
Like a good submissive crossdressing boy he bent over the bed and let his client’s husband fuck his asshole. Tim’s cock turned out to be quite a bit and it stretched him in a way he didn’t even think was possible. It definitely hurt but there was an interestingly pleasurable feeling as well. To get fucked was an experience that he knew he would be repeating soon and the truth was it felt really good wearing the satin slip too. Maybe he was becoming a true sissy slut.
While Tim was discovering his passion for sissy asshole his wife was discovering her own desires for everything crossdresser related. She had no idea it would be so arousing to watch a man get fucked by another man but her pussy was dripping wet and there was no greater evidence of passion and desire.
“Oh my God, Tim you look so good fucking that tight ass! Fuck it harder! Fuck that sissy bitch hard and deep! Pound his asshole with that big fat cock of yours!”
Joan was really getting into it, fingering her pussy furiously as she watched her man’s large dick disappear inside the tight asshole that was squeezing it so hard. Tim was almost certainly not going to stop fucking him now that he was getting encouragement from his wife. When he first got in the asshole he wasn’t even thinking about her but when he finally looked over and saw two of her fingers disappearing inside her wet pussy at the sight of hot crossdresser sex going on in her bedroom he knew that his wife had discovered something entirely new and wonderful. It was a sexual awakening that was going to change their lives forever from that point forward.
When his wife finally had her orgasm she collapsed back into the bed and simply laid there breathing heavily. Tim was still pounding away at Richard’s ass and the sound of their crossdresser fucking was reverberating through the house. It rang in Joan’s ears and in less than a minute she could feel the sexual pressure building up again.
“Tim, I need to suck cock,” she cried out as her finger once again found her clit and started rubbing.
Her hunky husband didn’t need any further encouragement. He slipped his dick from Richard’s tight ass and let his wife lick all the nasty juices off. She had always been something of a slut in the bedroom and she had no problem sucking on that dirty cock. The fact that it tasted like ass only seemed to turn her on more in fact.
“Richard, get over here! I want to suck both of you at the same time. I’ve never been so damn turned on and I can’t help myself,” she said with a gleeful smile.
Now the slut was on her knees on the floor with a dick in each hand and her mouth switching between the two. The beefcake was now a crossdresser wearing her lingerie and her husband has just finished fucking his sissy ass hard. She knew that her oral pleasures were getting them both wildly aroused and that they would soon be overwhelmed with the desire to fuck. That was all part of her plan because Joan’s ultimate birthday pleasure would be to get double penetrated.
She had dreamed of being taken in both holes since college when she had watched a double penetration porn video that one of her boyfriends owned. It aroused her even more than it did him back then but she had never actually tried to make it happen. How her husband had bought her a buff, well-hung stripper for her birthday so it seemed like fate was trying to tell her something.
“I want you two to double penetrate me. It would be the ultimate birthday present.”
Tim smile brightly and said, “Absolutely baby. I know Richard would love to fuck that sweet ass so why don’t you sit on my cock and put your ass up for him to nail.”
She did just that with Tim lying on the bed and her pussy enveloping his dick in warmth and tightness. He sighed in pleasure when he slipped inside her hot hole and because she was so loose and relaxed her asshole was no problem for Richard to penetrate. Just like that she was getting double-teamed with a dick sawing into her asshole and another one gently fucking her pussy.
The guys fucked the hot blonde slut as deep and hard as she could handle and she took every inch as a good girl should. They ended up trying a few other positions as well and the night came to a thunderous conclusion when both guys came on her face. She was drenched in jizz and thinking that they should all take a rest and then start in on round two.
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