As James approached the front door he reached absently for the keys in his back jeans pocket, striding up the steps to the door. Without thinking he reached for the door handle, and to his surprise it opened without any need for the key. He paused momentarily. Strange. Even if Michael was at home it was unlikely that he would have left it unlocked.
James cursed the luck that had him watching over Jack and Wendy’s house while they enjoyed a three week European vacation. He understood, though – Michael was staying behind, and even at 18 he still seemed very young. Even effeminate. James didn’t know if he would have trusted Michael to watch over things either.
Conscious that there may be strangers in the house, James stepped in quietly, slipped his shoes off as he shut it gently behind him. He surveyed the house briefly: nothing appeared to be out of place. He stepped forward gingerly, his feet making no sound on the tiled floor as he moved from the entranceway into the lounge. And then he heard – did he? – a murmur, a voice perhaps, a whisper from upstairs. The hairs on the back of his neck rose in warning. Even though he hesitated, he knew that he would have to go up; and so he moved to the stairway, stepping carefully as he climbed, counting the sixteen treads that that took him to the passageway between the bedrooms.
Here it was carpeted, and everything seemed normal, except for the reflected light that was seeping out under the half open door to the main bedroom. He slipped quickly to the side, peering into the room through the gap at the hinges, surveying the room quickly to see who was there. Of everything he had expected, though, the sight before him caught him unprepared.
The main bedroom was large. To the left stood the double bed, slightly out of James’ vision. Wendy’s closet was against the far wall, standing open. To the right was a full-length mirror, and standing with her back to the doorway was a woman – a girl perhaps – dressed in a full length formal dress. James recognised the dress as one belonging to Wendy – but it certainly wasn’t Wendy evaluating herself: this woman was thing, gangly even, and the dress hung slightly loose on her frame. James wondered if anyone else was in the room – it was conceivable that someone was on the bed out of view. He stood without moving, waiting quietly to see what was happening.
And then a voice – Michael’s voice – spoke: “Very nice. Now turn around.”
The woman rotated, still looking at the mirror over her shoulder to keep herself in view, but James saw her face, lipstick, rouge, mascara, blush, earrings, girlish tilt of the head and realised with a shock of amazement that he was staring at Michael. Michael – dressed in his mother’s clothing, parading before a mirror, made up like a woman, obviously using the opportunity while his parents were gone to explore personal fantasies. James realised that he had wandered into a private sexual exploration – Michael playing out a scenario for himself, watching himself, as a woman, in the mirror.
For a moment he wanted to turn and leave – but Michael was facing the doorway now – any movement might alert him to James’ presence. Motionlessly he appraised the scene. Apart from the makeup, Michael had obviously taken some time to prepare himself for this: James could make out the shape of breasts beneath the dress. Michael’s hair – always long – was blown back, hanging to his shoulders. James could make out strappy black shoes matching the black sheen dress, over grey pantyhose. Michael looked anything but a parody – he was deliberately dressed and posing to look like a sensual woman, and for all the world he did. As Michael spoke again, James began to understand the fantasy that was being played out – he alternated between two voices, a feminine lilt that was obviously the role he was portraying, and a deeper voice that belonged to an imaginary man – who James came to realise was supposedly interviewing Michael for a job.
Female voice: There. I hope you like what you see. I’m not used to being asked to do this for a job interview. Male: Well – we both know that you have interviewed for a lot of jobs, don’t we? And that you haven’t had any luck? Turn around again.
Michael dropped his head resignedly as he rotated to again face the mirror. James could leave now, but he was fascinated by this play taking place before him – by the voyeuristic opportunity that had presented itself. From the back Michael looked like a woman again – he had obviously posed this way a lot, and this was perhaps old sensual territory for him. He appeared to be a shy, coy woman as he spoke again.
Female: I haven’t had much luck, no. Jobs are not easy to find. I really do need this one. Male: There are many candidates that I have to interview. Work is hard to find. If you want this, you’ll have to prove that you have something to offer.
Michael raised his head and looked at the mirror, lips pouting slightly in feigned anger.
Female: I work hard. You’ll never have to worry about the quality of what I do. Male: That’s not what I meant. I meant that you’ll have to show me some of what you have. Female: I don’t understand. Male: Some of what you have under that pretty dress.
James was fascinated by the scenario: Michael fulfilling both the role of the aggressive, demanding, controlling manager – and the woman reluctantly being drawn into exposing herself. James recognised the type of fantasy – he had had it himself. How many men had not imagined having an attractive woman obeying his every command? It was built into most men’s psyche. And yet this was different; Michael was deliberately positioning himself not as the domineering manager, but as the submissive, reluctant victim obliged to obey these instructions in order to get employment – and James was intrigued. More than intrigued … as Michael mouthed the next words James felt a movement in his groin that alerted him to the impact this was having. This pretty boy/girl (for Michael was unquestionably attractive – as he shifted his stance slightly the movement of his ass under the dress caught James’ eye) wanted to be controlled, wanted to be a submissive little girl to a controlling male figure. Michael wanted to explore his femininity by pretending to be made to do this.
James had explored his dominant preferences more than once. Early in his marriage he had started to tie his wife up, once taking photographs of her as she lay helpless on the bed. That day had been a long, slow exploration in which he had bound her while still dressed, and then unexpectedly pulled out the camera when she could do nothing to stop him. He had taken pictures as he stripped her, and her first attempts to pull out of the ropes had only added to the erotic nature of the images. She had become progressively humiliated, especially when he pulled up her skirt and pulled the panties to one side, holding her knees apart and ensuring that her face was in each photograph, particularly the most intimate. Her muffled anger through the gag had no impact at all, until he pulled it away so that she could take him in her mouth. He remembered how angry and turned on she was simultaneously, tearing against the bonds, but still taking him fully into first her mouth, and then when he turned her over, between her soaked lips. No matter how she had raged afterwards, they both knew that she had been left drenched and wanting: she had bucked under him with abandon. And as time progressed ropes, scarves, and eventually even some handcuffs had progressively found their way into the bedroom. As the marriage had turned bad the domination had remained, becoming more overt. Once, as they stood against the back wall in an elevator, he had reached under her dress, pulling her panties down and letting them fall to the floor out of sight of the unsuspecting patrons; he had been too strong for her to stop him even though she frantically tried to hold them up for a few brief moments. Each time there would be anger followed by lust. As the marriage irreparably shred he started doing it in more public situations, pulling down her bathing suit in the pool once so their friends could see her breasts, reaching into her pants and cupping her while she tried unsuccessfully to pull his hand away, and all their friends laughed. However madly she had twisted away, even in those brief moments he felt how wet she was.
So the scene before him set his heart to beating, and even though he had never thought of himself as anything but heterosexual, Michael was just so feminine, so little-girl innocent as he shifted his weight to one leg and spoke again, that James suddenly realised that he wanted this woman – wanted to take her under his control, to make her satisfy his escalating desire.
Female: What do you mean? Male: You know what I mean. I mean that it’s time for you to show me some of what you’re wearing under there. Pull down the zipper on that dress.
Michael paused, dramatically, as if staring uncertainly as his tormentor. James was now erect and prepared to progress this to a more overt stage. As Michael reached behind him and drew the zipper down, exposing the indentations of spine crossed by a black brassiere strap James stepped out and stood in the doorway. For a moment Michael didn’t see him as he was concentrating on sliding it open, but then he looked up and James could see the shock cross his face as they looked into each other’s eyes in the mirror. For long moments neither moved, then Michael spun around, reached behind himself to hold the dress closed, and took two steps away, backing against the mirror. His face reddened furiously under the makeup, his eyes dropped to the floor – James knew that Michael was frantically trying to find an excuse, an escape from the shameful situation in which he had found himself.
James spoke first: “It’s alright Michael.”
Michael said nothing, continued looking at the floor.
“It’s alright Michael – I understand. You have to explore. We all explored things at some point in our lives. There’s no need to be embarrassed.”
Michael’s eyes flickered angrily up at him. “You’re not the one standing here in your mother’s dress!”
“That’s true.” James closed the door behind him. It was a meaningless action, but it seemed to reinforce the privacy of the situation in which they found themselves. “But you look very feminine like that.”
Michael didn’t react. There was a lounge chair off to the right of the door. James moved towards it and sat down, relaxing, comfortable in the role that he was creating. “You look very pretty like that, Michael. You know that, don’t you?”
Michael still didn’t move, pouting in frustrated anger now, looking more girlish than ever. “You look very … desirable.”
The words hung in the air, Michael’s eyes flickering across the floor from side to side as he absorbed their meaning. James crossed his legs now. “We could keep this all a secret, Michael. Nobody needs to know. Our secret.” Michael didn’t move, just listening, becoming the role that he had been portraying just moments before. “If you want it to stay our secret, all you have to do is follow my lead. Girls like you know what that means. Unemployed, needing whatever job they can find. Doing whatever they have to.”
Michael raised his eyes now – were there tears there? – and looked confrontationally at James. He opened his mouth to speak, but stopped before any words came out. James smiled. “I’m not like other managers, Michael – I’m not that interested in your tits. I want to look at panties, and pussy. Lift the hem of your skirt, and then come stand here in front of me.”
Michael didn’t move, still staring at James, then finally spoke – and his first words were angry: “I’m not your toy!”
“Oh but you are, Michael. If you want this to be our secret, you are exactly what I want you to be. Do you understand?”
Michael was pouting, lips trembling, so … beautiful. So desirable. James’ cock was raging, a steel bar that couldn’t wait to be released. “You are my toy, my slut, my plaything, Michael. You want to be. And I am going to make you. Again – do you understand?”
And again Michael opened his mouth to speak but no words emerged. He stood, at a loss, his fantasy suddenly a hard reality – what was so easy when he had the control of the fantasy had become quiet frightening, insecure, when he was a pawn.
“Lift up your skirt, Michael. Do it now.” Michael didn’t move for long moments, staring at James intense eyes, slight aggressive smile. Then he let go of the zipper he was holding shut, and the front of the dress fell loose. He bent over, eyes still on the floor, and his fingers hooked around the hem, drawing it up as he stood straight. “More”, said James. “Right up. Hike it up around your belly. I want to see panties.”
As the boy exposed legs encased in thigh-high pantyhose, with patterned, elasticized tops, and then black drum-tight panties James found it difficult to contain himself to the chair. He savoured the view: Michael had dressed for self-seduction, with semi-transparent underwear, his manhood almost visible through the gossamer stuff. His legs, sheer, womanly, trembling perhaps. The hands holding the skirt showing false red nails amongst the crumpled material. “You like showing yourself to me, don’t you Michael? You fantasy is coming true, isn’t it?”
Michael just turned his head to the side, non-commital. James reached out one hand and let his head fall to one side, but his eyes never left the image before him. “Come here – come stand in front of me”.
Michael walked across the floor, balance still unsure on his mother’s high heels, until he stopped, exposed to James examination, inches away from the chair. James placed the back of one finger against the inside of a knee, and then trailed it up across nylon, flesh, the softness of the inner leg, to the hollow just below the panty mound. Michael’s eyes closed, and James could see the slight movement inside the panties that belied Michael’s emotions. He restrained himself from reaching up for the front of the panties, savouring rather the agony of confusion and lust crossing the boy’s face. “Turn around Michael. Keep the skirt up – I want to see your ass.”
Michael swivelled, perhaps relieved to be turning away, but James suspected that Michael was beginning to enjoy the realisation of his desire. The dress may have been slightly loose, but the black French-cut panties fit neatly, the light reflecting erotically across the curves of his ass. James ran his fingers across the smooth material, trailing down the crack of Michael’s butt, slipping two fingers between his legs to find the stretched material encasing Michael’s testicles. “Turn around”. As he spoke, he realised how dry his throat was.
And now, as Michael turned into view, it was evident how turned on the boy had become: the panties were stretched into a tent with the head of his cock peering out beyond the elastic at the belly. Staring into Michael’s eyes, James reached forward and pulled the front of the panties down, exposing Michael fully for the first time. As his fingers brushed against another man’s cock for the first time, he heard Michael sigh and push his hips forward, cock standing out like a tower, demanding attention. “You’re so pretty”, said James, touching it with his fingertips, exploring this new experience, listening to Michael’s laboured breathing.
It was strange how erotic this sight was: Michael’s cock, distended with lust, the panties bunched under his testicles, pushing them forward. It was as intimate as the first moments when a woman exposed herself, lying back for him and spreading open her legs for his gaze. As erotic as it was for them both, it was also true that their passion play contributed to the lust of the moment. And so James continued to play it out: looking up into Michael’s eyes, and with a cruel smile on his face he said: “Naughty girls showing themselves to strangers. Pussies this naughty need to be slapped –pussy slaps so hard that your eyes water and your mouth goes dry.” His hands had wrapped around the shaft now, was masturbating Michael with slow, measured strokes that caused Michael to move his hips in rhythm. “What do you think.”
Michael spoke almost in a whisper. “I’m not that naughty – it’s the job. You’re making me misbehave.”
“Then perhaps it deserves a licking?” At this James moved forward, and for the first time (what a day for firsts this was!) he felt the pulsing hardness of a man’s cock across his tongue. How strange that this should feel so natural. How strange that he should know to draw the length of the cock into his mouth, moisten it then withdraw, leaving Michael to suddenly feel coolness against his flesh; how strange to know that the tip of his tongue could find the sensitive channel between shaft and head to tease, or that it could press into the opening at the tip and split it just slightly, just enough for Michael to lose composure, drop his hem which fell about James shoulders, and to take James head in his hands as he pressed forwards into his mouth, filling him, embracing him with the cloth of the dress. And now James found himself under this boy-girls’s clothing, the eroticism heightened by the voyeuristic sense of being up Michael’s skirt, light coming through the material to this hot, confining place of sex, Michael’s hands cupping his hair through the stuff of the fabric, pulling him forward onto the rod. He drew back until the cock-head was held in his lips (for a sudden, ludicrous moment he remembered referring to woman as having CSLs – cock sucking lips – and wandered if that applied to him too); and then reached for the panty-fabric and pulled it down to Michael’s knees. God this looked sexy – pantihosed legs open, panties stretched between them, red, moist cock demanding attention under the tent of the skirt.
After savouring the view for long moments, James pulled back from under the skirt to look up at Michael’s face, flushed with requited lust now; his fantasies suddenly, gloriously realised, his unremitting desire expressed in hard breathing, focused gaze. James hands were still under the skirt, one hand cupping Michael’s ass, the other still stroking him tenderly, enjoying the sensation. “I think you should sit on my lap, little girl”, he whispered.
But now, for the first time, when Michael responded, there was a new timbre to his words – and he progressed the game in a wholly unexpected direction. He dropped his head girlishly to the left, brushed back some hair from his eyes: “Yes daddy, if you want”.
Ohhhh. How could words evoke such a response from James’ cock? Michael moved to the left, tripping slightly over the panties still binding his knees together, then sat across James lap, putting arms around James’ neck, nuzzling his face into James neck. “Like this, daddy?”
“Yes my girl – just like that”. James reached down and pulled the hem back up, hiking it to where he could again see the boy cock, knees held by the panty. He touched Michael’s shaft softly, again starting to stroke him, still in wonder at the rigidity and beauty of the rod between his fingers.
Michael was whispering now: “Are you going to kiss me, daddy?” It was a girl’s coquettish question. James turned his face, their lips coming together for the first, soft gentle exploration that added an emotive, sensual depth to this discovery. They kissed forever, slowly, hesitatingly at first, then tongue tips testing until finally it was an embrace, an acceptance. Again James was struck how natural it seemed to be catching Michael’s lips between his as he felt the contours of this wonderful girl cock in the palm of his hand, both men breathing deeply, hearts racing – but with a different sense: this had turned from coercion to shared seduction now. They withdrew slowly, Michael whispering again: “Are you going to fuck me, daddy?”
“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.”
“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 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.