Michael in the Mirror

"I think I should, don't you?"

Michael nodded gravely, his eyes never leaving James. "I've never been fucked, daddy. I'm quite nervous."

James spoke seriously for a moment: "I've never done this either Michael. We'll have to do this carefully, together, won't we?"

Michael nodded, obviously anxious, but satisfied for the moment. His hands had reached down between them, and James adjusted himself to give Michael free access to his zipper. Michael was looking down as he unzipped James trousers, keen to see this man's cock, making a slight girlish noise as he drew it out for the first time. His hands were cool, soft, tentative touches; his eyes watching everything, examining James cock from every angle he could. James, in the interim had slid his hand down past the testicles, but he couldn't go any further because of how Michael was sitting. "Lift your legs for me". Michael had to release James' cock so that he could lean back, lifting his legs up to his chest, James now getting a clear view of the boy's ass.

Michael's cheeks were slightly open, the ring of his anus exposed to James eyes and fingers. James slid one finger between the cheeks, stiffening his finger to press up against the nub. It wouldn't open – Michael was clearly too nervous. "Pull your knees up higher". Michael did as he was told, and James looked across to Michael's mother's dresser, where a bottle of lotion stood amongst other paraphernalia. "Stay like that, my girl", he said, as he reached over, collected and opened the bottle and then squeezed some of the pink lotion directly onto Michael's tight opening.

"That's so cold", Michael said, his anus tightening momentarily. James wanted that little ring wrapped around his cock so badly now; he rubbed the lotion tenderly around the ring, feeling it warm up, his finger sliding easily around until he pressed it up again, demanding the access that now came with a slight moan from Michael. James put one hand on Michael's knee, holding his leg up and open, keeping the ring exposed to his penetrations: his index finger slid in against the resistance, and Michael's girlish sighs only increased his desire. Michael's hand had found it's way back to James cock, and he stroked James as the finger penetration continued, more easily, the anus not relaxed, but less tightly closed. Michael's legs opened and closed slightly in rhythm with the anal invasions, his breathing a bit ragged. The men lost themselves in the moment, James replacing his index finger with the thicker, stronger middle finger, opening Michael up in preparation; until he withdrew the finger and spoke again: "Are you ready to sit on my cock, my girl?"

Michael nodded nervously. "Yes daddy, I am. You'll be careful, won't you?"

"You know I will." Michael leaned forward, and pulled the panties down, kicking them off his ankles, and opening his legs to turn and place his knees outside James' thighs. The boygirl faced the man, placing hands on his shoulders as Michael started to lower himself. James held his cock, moving it to the anus, ready, waiting. Michael bent his knees until the point of contact arrived, and then paused before pressing himself down. The expression on his face showed the difficulty of the entry. After a moment he stopped: "I can't do this – it's too painful."

"It's ok – we'll try another way. Bend over against the bed."

Michael lifted himself off James lap and walked (so-o sexy!) to the bed, glancing back across his shoulder as he bent forward and placed his palms on the bedspread. James walked up, lifting the skirt and tossing it over the boy's hips. The sight was as desirable as anything he could remember: pantihosed legs straight, skirt flung in disarray over hips, long hair hanging down over Michael's face, ass open, waiting. After hastily pulling off his trousers and underwear, James squeezed some lotion into the crack of Michael's ass, and a bit more over his own cock. Michael winced expectantly, cold again. James slipped a thumb down the boy's crack, opening it up until he could rub the lotion in, pressing the thumb up his bottom. Then he placed the head of his cock against the ring and paused. The boy, eyes closed, tightened his thighs slightly. And now James pressed forward, pulling the cheeks apart with his hands and he rammed ahead, feeling the anus open and then close around the head, and Michael's breath rushing out. "You ok, Michael?" Michael just nodded wordlessly, and so James pressed forward, watching the length of his shaft slide deeply into the boy. Michael's hands clutched the bedsheet, the sole expression of the pain that he must have been feeling; but James was beyond the point of no return: he started to stroke in and out, long piston moves, the anus tight and breathtaking around his cock. And Michael seemed to accept this, his hips beginning to press back against the strokes, especially once James reached around to stroke him at the same time. The strokes came quicker, flesh slapping, guttural moans now from Michael, until James felt the pressure in him rising, exploding, and he cried out as he expelled himself into the boy.

Michael could also take it no longer; James felt Michaels cock pulsing in his hand, and his cum shooting out past James fingers onto Wendy's dress and bedspread, his breaths coming in short, sharp jerks of passion.

In slow motion the two fell forward and lay spent on the bed, James cock softening and sliding out of Michael's body. They stayed like that, recovering, breaths slowing. Finally Michael stirred under the weight, and James lifted himself up to let Michael turn and face him. They pulled themselves up on the bed until their heads lay on the cushions, and they smiled at each other, holding each other's eyes. Michael moved closer and kissed James fully on the mouth. "That was my first time."

"And mine".

"Well – with a boy, but not your first time ever!" He crinkled his nose. "That was nice, but I'm sore now."

James nodded. "I'm sure."

He pulled himself over, lying on Michael now, kissed his eyelids softly, aware with a painful erotic sense that his cock was touching Michaels, and that Michael was moving against him. They rubbed against each other in a post-orgasmic slow dance, cocks already responding to this renewed lust. It was too soon for James; he wouldn't manage another penetration now, and Michael was probably too sore anyway; but the look in both men's eyes reflected fresh desire.

"Thank you daddy", said Michael.

"Thank you my girl".

"Do you think we'll do this again?"

James paused before answering. "I don't know. I think so. Perhaps."

Michael smiled. "I'd like to do it again. With you. You will always be my first, won't you?"

James smiled. "I suppose I will."

"But next time I'll wear something different. Maybe a one piece bathing suit, and we go for a swim together?"

James considered that, lifting his body up slightly so that the length of his cock could slide along the length of Michael's. "I'm an old fashioned guy", he said. "A short skirt with French cut panties, or real garters and stockings?"

A mischievous look entered Michael's eye, as James felt his hand slide between them. Michaels fingers wrapped around them both, pinioning the two shafts together as he began a languorous stroking motion. "My mom's wedding dress? So we share a wedding night together?"

Ohh. James swallowed.

Michael teased again: "With wedding underwear, patterned stocking, a veil? A blue garter? Just for my daddy?"

James nodded. "You're really a tease, aren't you?"

Michael giggled. "This was so wonderful for me. I like to tease you."

James nodded. "Our wedding night, then." He drew a stray lock of hair off Michael's face. "This place is a mess now, isn't it?"

Michael grimaced. "I'm going to have to wash these clothes and this bedspread." He lay back. "I'll wear an apron and nothing else while I do it, so you can think of me…"

James laughed, "You know I will." He kissed Michael again. "It's time to go."

Michael pouted. "I know. But you'll be back tomorrow night? For the wedding night?"

"Oh yes. You'll be pretty for me, won't you?"

Michael giggled. "Like a picture, daddy. Like a picture."

James pulled away, and got up to find his crumpled trousers. He glanced across at Michael, still lying on the bed, hair dishevelled, legs open, dress still up about his waist, cock half-erect, Michael watching James every movement as he pulled the trousers up. He walked across and sat on the bed again, touched Michael's cock, then reached under him to find a moist ass. He slipped one finger between the cheeks to touch Michael's anus softly, and saw Michael's cock rise slightly in response. "This belongs to me now, doesn't it?"

Michael stared at him, looking like the naughty little girl he was, eyes peering through fringe. "Whenever you want it, daddy."

James smiled, leaned over and kissed Michael for the last time, then stood up and walked out of the house without looking back.

"So this is what I am now", he thought, wondering whether this would ever again happen with anybody else. "So this is who I am."

Strange, really.

Strange that it felt so right. He reached his car and got in. As the engine gunned to life he pondered what a groom should bring to a wedding night with his new girl-boy. Perhaps a camera, he thought. All weddings deserve pictures. And he pushed the car into gear and pulled away from the kerb.