Chapter 3: Before Their Wedding 1

Once the plane was in the air, Barry and Gloria ordered drinks and were soon lost in their individual reveries. Thinking about how Courtney Murray had taken Gloria under her wing caused Barry to remember his first tentative steps into the world of cross-dressing. He was embarrassingly bad in the beginning. Barry knew that now but wasn’t aware at the time. Using various online tutorials, Barry thought he’d done a respectable job of turning himself into a tubby, middle-aged woman. He invited Neil over, hoping Neil would want to help him explore man-on-man sex some more. So far, Neil and Barry only got it on together when they fucked Gloria, and she insisted.

Neil turned up and immediately broke into laughter. “Baz, what the fuck?” He chuckled. “You look like my uncle trying to look like my aunt and failing abysmally.”

Barry was mortified and vowed never to cross-dress again. He sent Neil home. However, when Gloria came over later that day, she spotted his lingerie dumped in the outside bin. Discovering the rest of his outfit, she brought it inside and forced Barry to put it on. When he was dressed, Gloria shook her head and insisted he shave all his body hair off. Barry resisted, but Gloria overrode his objections, pointing out he worked in a freezer and wore long trousers and long-sleeved shirts so no one would know he was hairless. And even if they did know? So what? She certainly knew he wasn’t gay!

Barry returned to the lounge after reluctantly shaving his entire body. But his complaints died when Gloria moaned lustfully and pounced on him. His cock disappeared inside Gloria’s mouth, and his cum spat down her throat shortly after. Then, his fiancée bent over his kitchen table, and Barry stood on the phonebooks, urgently driving his meagre five-inch cock into her dripping cunt. Gloria and Barry spent the night going ‘around the world’. He fucked her mouth, cunt, and arse in rotation until he could go no more. Then he used his tongue and fingers until Gloria was finally satiated, and they slept.

The following night, Gloria did Barry’s makeup and helped him to dress. She’d bought breast forms (C-cups), a blonde page-cut wig, and tucking tape to ensure Barry looked as feminine as possible. Gloria also purchased a much shorter, tighter dress for Barry to wear along with stay-up black stockings. She hadn’t bought shoes because she didn’t know his size, but she intended to take him shopping for those and more dresses later.

Gloria knew what she wanted that night and had come prepared. Once she had Barry feeling comfortable about being dressed as a woman, with his cock and balls tucked and taped away, she dropped her skirt, revealing her six-inch strap-on cock. She bent Barry over the kitchen table, lubed his fuck hole, and gently pegged him until his ass was well stretched.

Then, giggling happily, Gloria phoned Neil and insisted he come over. When he arrived this time, Neil gaped at his friend and felt his cock throb as he imagined fucking him. Neil was perhaps a little more bisexual than he cared to admit because he’d gone from freaking out after fucking his best friend to enjoying doing it regularly. It helped that Gloria’s rampant sexuality overcame any squeamishness he initially felt. Looking at Barry kneeling before him on all fours, dressed like a wanton slut, had Neil eagerly anticipating what Gloria had planned for them.

“What are you waiting for, Neil?” Gloria asked with pretend exasperation. “That slut won’t fuck itself.”

Neil gulped and dropped his shorts. Grabbing his solid six-inch cock, Neil knelt and lifted Barry’s tight dress above his pudgy ass. Then, seeing Baz’s hole was already oiled and gaped, Neil forced his rampant cock through Barry’s knot and deeply into his colon.

“A good slut reaches between her legs and fondles her lover’s balls,” Gloria pointed out. Barry groaningly complied, not realising there was an ulterior motive for Gloria’s demand. The change of angle meant the next time Neil drove into Barry’s ass, his cock rubbed over Barry’s prostate.

“Oh, fuck!” Barry grunted in pleasurable surprise, his fingers frozen on Neil’s balls. Neil pulled back and thrust in again. “Oh, Gawd!” Barry moaned, his tiny cock trying to stiffen despite being taped back.

Neil was uncertain of what was happening, but he knew his friend was enjoying being fucked more than he ever had before. So, gripping Barry’s plump hips firmly, Neil fucked him hard.

Barry’s cock couldn’t stiffen or enjoy being stimulated, but he felt a desperate need to cum. Wanting to achieve Barry’s desire, his mind took over and centred its orgasm trigger on Barry’s prostate. The next time Neil thumped into his ass, Barry climaxed, spitting cum from his cock’s eye despite it never becoming hard. Orgasming from prostate stimulation without penile stimulation is similar to a G-spot orgasm for a woman. Barry’s body reacted to cumming more intensely than it ever had, and he sagged down, lost in bliss.

“Don’t pull out,” Gloria demanded. “But hold still for a second.” She knee-walked up behind Neil and placed her hand on his tailbone. Neil felt Gloria’s strap-on cock against his pucker hole and hoped it was her smallest one. “Good boy,” Gloria panted as she slid the lubed dildo she used on Luna and Barry into Neil’s ass.

It took a little while before they learned how to time their thrusts, but soon, Gloria was fucking Neil as hard as Neil fucked Gloria’s fiancé. Neil lost control first, emptying his aching ball sack into his best friend’s ass with several delighted grunts. Feeling Neil’s cock spewing cum over his prostate, Barry exploded from another P-spot orgasm.

He collapsed off Neil’s cock and wanted to sleep but knew Gloria hadn’t received any reward for creating this sexual masterpiece for Neil and himself. So, fighting off his lethargy, Neil slid between Gloria’s wobbly thighs and latched his mouth onto her dripping cunt. Gloria fell back, sighing happily. Her lover’s cock may have been unimpressive, but Barry more than made up for it with his oral and finger skills. Gloria orgasmed harder and more often with Barry than with any lover other than Luna she’d had before, which reminded her that it was past time to give Barry another taste of his little treat.