A Crossdresser's Love Story

As they lay there kissing each other and relishing the taste of cum between them, Jim's throbbing cock pulsed against Wendy's spent one.

"Hmmm, I know what we can do with that!"

Sliding down, she slid her lips over his cock again and gently began to swirl her tongue over the tip. He turned and moved into the classic 69 position and began to suck her again. They lay there for a bit, sucking each other, their mouths moving in unison.

Wendy pulled away for a moment

"Jim, I want you to make love to me like a woman, put a finger into my man-pussy and loosen me up. I need you to fill me."

Jim let his hand slide over Wendy's smooth ass until the tip of his finger touched her puckered opening. He slowly worked it into the tight opening bit by bit, wondering how he would ever get his cock in such a small hole.

He had never done anal; his wife of 30 years wasn't into it. He decided that Wendy's anus would need some lubrication. He traced down her balls with his tongue then to her man-pussy. His tongue replaced his finger as he worked it into the musky hole fucking her with his tongue.

Wendy gasped when his tongue entered her and thrust back against his mouth, spreading her legs as much as possible.

Jim worked at her hole, his tongue probing and thrusting, making it softer and looser, the musky smell was driving him wild, and he wanted her more than ever.

He sat up and turned her on her back. Jim spread her open, holding her ankles. He placed the tip of his cock against her wet man-pussy and slowly pushed in, watching as his cockhead disappeared in her starfish, feeling the warm embrace of her hole as his knob entered her anus.

Wendy couldn't believe the feeling. She had vibrators in her rectum. Before she got sick, Ellen fucked him with a strap on. But this was his first cock, and it felt amazing!

There was a bit of pain; Jim had a big dick! The head of Jim's cock slipped past her anal rings, then the wonderful feeling as it slid deep into her, sliding across her prostate.

Wendy went wild as Jim's shaft repeatedly rubbed her prostate, sending indescribable sensations through her.

" Oh yes! Jim, please fuck me. I need to be fucked hard. Use my pussy... please!"

Jim put her legs over his shoulders. His cock sank in until his balls slapped against Wendy's ass. The tightness of her asshole was more than he could bear. He stroked in and out of her as his balls tightened

Wendy's man-pussy was tighter than his wife's pussy and felt better.

"oh Lord, you are so tight, I can feel a load building in my balls," Jim said

"Ugh!" "Yes! Yes! That is the way Jim, pound me! Make me your bitch!"

Wendy grabbed her ass and pulled the cheeks apart, letting him go as deep as possible. She loved the feeling of the tip of his cock bouncing off her prostate. Her cum rose from her prostate being massaged by her friend's shaft

Wendy grabbed her cock and began stroking herself, enhancing the feeling of being fucked.

Jim was totally into ass fucking his buddy now. It seemed a bit weird at first, but now it was the most erotic experience of his life.

"Let me do that, Jim said, brushing Wendy's hand away and taking her cock in his hand. He struggled to hold her legs on his shoulder while masturbating her.

"I'm going to cum!! Yes! Yes! Deeper! Deeper! Yes!"

A jet of cum sprayed from her cock all over her chest. Her cock pulsed spurt after spurt with each plunge of Jim's cock into her bowels. As he pounded into her, her cum squirting triggered him

" Here it comes! Now! Now! Ugggh!!!"

Jim's back arched as he dumped a massive load into Wendy's bowels.

"Yes! Yes! I can feel it oh yes!!"

Each spurt of Jim's hot juice washed over her prostate, enhancing the pleasure of her orgasm. Her cock sprayed drops of cum with each push until she completely drained.

Jim collapsed on her, his cock still buried deep in her, sandwiching their hot sticky cum between their bodies. Wendy wrapped her legs around him and held him close, not wanting the moment to end.

"Wow," he gasped, "that was amazing!"

"Yes, it was," Wendy said, feeling warm and cuddly wrapped in the afterglow of good sex.

Jim sat up and grimaced as his cock slid from Wendy's ass. He felt odd, looking down at her knowing he had just fucked his BFF.

"What happens now," Jim said, turning and sitting on the side of the bed.

He was having second thoughts, most of which concerned his sexuality. He had fucked Wendy and enjoyed it. He wanted to do it again. What did that say about him?

Jim worried about his marriage. Did fucking Wendy mean he cheated on his wife?

Wendy sat up next to him, lay her head on his shoulder, and wrapped an arm around his waist.

"Are you having any regrets?'

"No! Well, yes! I don't know! I'm so confused!"

Wendy stroked his chest, trying to ease his discomfort. She held up her hand and giggled.

"We're covered in cum," she laughed, "let's take a shower. I can't send you home to your wife with cum coating your body."

"What do I tell my wife," Jim asked rhetorically, "that I came by to comfort you, and we fucked?"

"It's up to you, Jim! You can tell her nothing or everything. I'm prepared to live with your choice."

Wendy stood in front of Jim, lifted his chin with a finger, and stared into his eyes.

"You were my first. Like most girls, you remember the guy who took your cherry. If we never do it again, I'll have that memory."

Wendy walked into her bedroom, turned on the water in the en suite shower, and adjusted the temperature. She started when she felt Jim's hands on her waist.

"Mmm! I hoped you would join me!"

Wendy bent forward, the steaming hot water washing over her as Jim pushed her in her back. She was surprised to feel his hard cock press against her anus.

"You're hard again," Rodger/Wendy marveled, feeling Jim enter her

"That's a first for me," Jim said, stroking deep in Wendy's man pussy while wrapping his arms around her and stroking her cock.

"Baby, you feel so good in me," Wendy said, pumping back, burying her friend and lover's cock deep in her bowels. "have you decided what you'll do about your wife and us?"

Jim's lips pulled back, exposing his teeth in a snarl. He viciously slapped her ass.

"This is our secret! Perhaps we'll tell her one day, but Rodger is still my friend and fishing buddy for now. And Wendy is my side piece!

Wendy smiled, feeling her lover's cock swell in her man pussy. He knew his wife would approve!

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