Something New: Changing it Up

My life soon settled into a delicious routine. During the week I was my normal self. I went out with the guys after work, but always had an excuse ready for weekend invitations, unless they were during the day. But my nights were for Sheila, no exceptions.

Sometimes I'd go back to the gloryhole, when all I wanted was to drink cum. One more time I had a random guy come around and fuck my ass raw, but most of the time, I had TrapFinder dates lined up. After RideMyCok74 I rarely had more than a single date with a guy, unless it was clear he was only down for sex. I didn't want to break any hearts, only suck cocks and get fucked like the slut I was. I loved my life, and I no longer questioned if I was gay or not; I guess I was bisexual, though it really felt more like I was two different people; but Sheila had a lot more fun.

Then something different happened. I matched with someone on TrapFinder who didn't match the normal demographic; it was a woman. She was looking for a 'gurl' to go down on her, then fuck with a strap-on. At first I wasn't sure how I felt about this- how Sheila felt about it- but as I looked at her pictures, including a few with her large strap-on jutting proudly I felt stirrings of desire, and knew I'd have to give it a shot.

When I messaged, she was very happy with my pictures. She admitted she'd not had a lot of luck, so after talking a bit, we made a plan. We'd meet at her place, where she wanted to help me prepare, do my makeup and everything else. While I felt like I'd gotten pretty adept, I was excited at the prospect of having someone who'd grown up as a woman to help me out.

When the day finally came, I packed up a few different dresses and sets of lingerie, and headed over. She answered the door in a colorful blouse and jeans that she filled out beautifully, and led me back into her room, and told me to strip. I'll admit I was a bit bashful; No one had seen me completely naked since the divorce, and given how hot she was, combined with my expectations of what was to come had given me a raging hard-on. Still, I did as I was told and soon stood completely exposed to her. She looked me up and down with an approving eye, seeming not to notice my modest erection.

"Oh, this will do nicely," she said. "I wasn't sure how much of your pictures was just camera angles, but you've got a lot to work with." I blushed, pleased at her compliments. "There is one small problem, though. What to do with this?" With those words, she reached out and grabbed my cock, meeting my eyes as she did so.

"Sorry," I said, embarrassed. "Normally I have it well tucked away, but you said to come over in my normal clothes."

"It's nothing to apologize for," she chided gently. "It's a perfectly beautiful cock, but we do need to take care of it." Then she promptly dropped to her knees and swallowed the head of my cock. I groaned as much in surprise as in pleasure as she slurped it into her mouth and bobbed on it with a will. She didn't seem inclined to tease, but grabbed my shaft and stroked it hard, using her own saliva as lube while she expertly sucked and worked with her tongue. As eager as I'd been, I'd avoided touching my own dick for the last day, and I was building fast. My hips started to buck as the pressure mounted, gently fucking her mouth as she went faster and harder. Finally, I arched back and groaned as I burst my load, the first time I'd ever come in anyone's mouth. She milked my cock, squeezing gently with her hand, draining every last drop into her warm mouth. Then she stood up and smiled at me, and leaned in for a kiss.

I'd tasted my own cum, of course, but there was something amazingly sexy about tasting it from her lips. She spit a surprisingly large load into my mouth, then followed it with her tongue, playing with mine as I swallowed it all down. When she pulled away, I opened my mouth to show her, like the dutiful cumslut I was, and she giggled.

"Oh, you're going to be a lot of fun."

We went to work after that, with her taking a mix of gentle but firm guidance and a more hands on role. She watched my shave my legs and gave me tips for harder to reach areas, but when it came to my pubic hair, she took over, carefully sculpting the hair into a neat landing strip. She relaxed and watched again as I shaved other parts of my body, asking questions and giving advice, until I was smooth all over, and feeling extremely feminine.

Afterward, she did my makeup, her eyes intent as she carefully lined and rouged and powdered. I gave her a little advice here for de-emphasizing my already ambiguous masculine features, and the result was a lot subtler than my normal makeup job. Of course, I was usually dressing for a manly audience, and my makeup was more of a disguise than an enhancement. Overall, I really liked it, and resolved to take her tips to heart for the future.

She let me dress myself, though she helped me pick the outfit. With the subtle makeup, she surprised me with a deeply slutty outfit, with black and red fishnets, an open-ass pair of lacy panties and some of my larger breastforms filling out the matching bra. Over those, she selected a sheer red babydoll that revealed my undergarments, and my favorite auburn wig. Altogether a very sultry look, and she stood behind me as I admired myself in the mirror.

"Now," she said, slapping my ass playfully. "What shall we do with you?"

"Whatever you want," I said teasingly. "But you've got to tell me."

"Hm," she purred. "That sounds intriguing. What if I told you to kiss me?" I winked, but did not move in until she smiled and rephrased. "Kiss me." I leaned in and kissed her, firmly and felt her arms snake around my waist and down to cup my ass. I let my hands roam, but kept them above her hips until she reached down and firmly placed them on her butt. I groped while exploring her lips, tasting her tongue, remembering the tang of my cum in her mouth from before, wondering if I'd get another go at it. Honestly, though, I didn't care; whatever she wanted would be fine with me.

"On your knees," she said, pulling away from my kiss. As I complied she added, "undress me, slowly." I reached up and unbuttoned her jeans, then slid the zipper down, exposing a firm midriff and the tip of a perky strip of hair that matched the one she'd given me. I could smell her arousal, but made myself work her jeans over her rounded hips gradually until she shucked them off herself, revealing a low-cut thong that barely covered anything. Then I worked my hands up under her blouse, feeling the soft skin of her belly and ribs, deliberately trailing my fingers as I raised her shirt over her head.

She was a beautiful woman, with a figure that made me both desirous and deeply envious. I'd never have that narrow waist or those full hips, but at least I was getting to touch her gorgeous body. She smiled at my warm regard and spoke again.

"Please me, tease me," she ordered softly, and I rose up to pull her to me, putting my mouth on the upper curve of her breast while I reached around with experienced fingers to release the clasp of her bra. I worked my way down and took her already firm nipple into my mouth and sucked on it, drawing a gasp of pleasure from her. I worked her other nipple with my fingers, while my other hand caressed her ass gently. I switched back and forth a few times while her breathing grew heavier; I didn't think I'd get her to orgasm, but it was obvious that she was enjoying my attentions. Finally I worked my kisses down her firm belly to the tidy patch of hair that peeked out of her skimpy thong, then firmly slid those down over her generous hips, as well. It released even more of that tantalizing aroma as her pussy came into view, trimmed and smooth and already glistening with moisture from my attentions. I leaned forward and tasted it with my tongue, lingering on her clit as I lapped it up.

She stepped away, taking me by the hand and leading me to the couch where she lay back, giving me full access to her glorious opening. I took a moment to admire it; I hadn't seen one since my ex-wife, and she'd hated having sex with the lights on, when she'd allow me to touch her at all. I don't know how I'd ever lived like that, but I was surely going to make up for all the time lost. I dove in, drawing my tongue up the full length of her slit, slipping my tongue inside and coming away with a load of tangy juices for my troubles. Then I focused on her clit while I explored her pussy with my fingers.

Susan hadn't liked me to go down on her. I'd done it a few times when we were dating, and once or twice before we'd dated, but once we'd gotten married she'd put her foot down on anything other than missionary intercourse. While I'd had a lot of fun trying new things since the divorce, this was the first woman I'd been with since, so I was a little bit hesitant at first. When she moaned and thrust herself into my face with each tentative lick, I grew bolder, flicking and sucking on her clit like a tiny cock, while I slid my fingers in and out of her well-juiced pussy.

"Oh god, " she moaned, "Oh, Sheila, please, don't stop." I found that I liked that very much, even in a woman's voice, and I happily slurped and finger-fucked her as her motions grew ever wilder. I crooked my fingers and tried to find the rough patch I'd heard about, deep inside her slippery cunt, while locking my lips around her clit and working my aching tongue back and forth. When I finally found what I was looking for I was rewarded by a gasp and a sudden sharp thrust of her hips, then her knees locking around my head as her body spasmed and twitched. I felt a warm rush of moisture around my fingers, so I released her clit and dipped lower, replacing my fingers with my tongue, lapping up as much as I could before she relaxed and pushed me away.

"That was fantastic," she sighed, breathing heavily, her well shaped breasts and still-erect nipples rising and falling in an unsteady rhythm. "Get yourself ready for the next part, and I'll be back soon." With that, she unsteadily rolled to her feet, reaching into a drawer to pull something out.

Obediently, I positioned myself at the edge of the bed, and flipped up the short hem of my babydoll negligee to expose my ass. Instead of walking around behind me, she surprised me by crawling up on to the bed in front of me, and I saw the flesh-tone strap-on protruding from her crotch as she positioned herself in front of me. I looked up at her and saw her smile with excitement and anticipation.

"I think you know very well what to do with this," she teased in a low, husky voice. It was all the prompting I needed, so I leaned forward and took the head of the life-like dildo into my mouth. It wasn't what I was used to; instead of the musky taste of man, it had the sterile taste of plastic, and it was cool rather than warm between my lips. Nonetheless, I treated it just like I would the real thing, teasing the head and the slit with my lips and tongue before slowly sliding down the length of it until it bumped the back of my throat. Just as slowly I pulled back, applying suction and working my tongue. While she couldn't feel everything I did, it was so ingrained by now that I did it without thought. I looked up into her eyes as I did so, seeing her smile as I sucked her ladycock like the slut I was.

It didn't take long for her to want to move on; while I enjoyed it and could tell she was too, it wasn't the same for either of us. She slipped it out of my mouth without warning, so there was a slight pop as the suction released, and stroked my cheek with her hand before crawling off the bed. I heard the spurt of lube as she moved around behind me, and the soft sloshing as she stroked it over the length of the strap-on. Another spurt, and a cool dollop of slick lube splashed into the crack of my ass, which she massaged teasingly into my asshole with one manicured finger. I leaned back against her finger and arched my back, urging her deeper. She obligingly began a slow, steady finger-fucking, drawing a moan of pleasure.

"You're really quite the butt-slut," she marveled," aren't you?"

"I'm whatever kind of slut you want me to be," I gasped, rocking my hips in rhythm with her penetrating finger. "Just fuck me already!"

"Very well," she replied, and slipped her finger from my ass with a barely audible pop. The disappointment that followed was quickly overwhelmed by anticipation as she positioned herself behind me, and I soon felt the insistent pressure of something much thicker. "Hard or slow?" she asked.

"Hard," I said. Normally, I preferred a slower approach, but I'd taken enough cocks to know how to relax my ass in preparation for a good hard entry, and I was thoroughly lubed up. I could also tell that's what she wanted, which was proven by the immediate thrust of her hips, driving the beefy dildo deep into my ass and pushing me down onto the bed. She withdrew slowly, and I could feel the veins of her firm cock as it slipped from my ass. She followed up with another solid thrust, shoving the dildo back into my ass, and drawing a gasp and a moan from my lips. She pulled out once more and I could feel the head slipping out of my puckered hole before she rammed it back in, bringing another moan. I could tell she was really enjoying my vocalizations, so each time she shoved her dildo in, I gasped and groaned and moaned even harder. I wasn't even faking, because it felt so good, but all the same I was glad when the thrusts started to come a little quicker, more regularly, until she was fucking me properly and I could feel the growing sensation I'd come to enjoy so thoroughly.

I knew it would take a while, considering the blow job she'd given me when I'd arrived, but I was game for as long as she was willing to fuck me. I'd sometimes not even cum when the guy was quick, but I was generally okay with that. Trapfinder had a lot of thirsty guys who just wanted to get their nut, but since I'd gotten my start as a cocksucker, I was fine with some cum down my throat or in my ass and calling it a night. Many of my lovers were more considerate- or at least longer lasting- so I'd received plenty of anal orgasms, and hoped that tonight's lover would fuck me long and hard.

For certain, she didn't show any sign of flagging soon. Her strokes were long and deep, and I could feel her smooth, muscular thighs slapping my ass with each hard thrust. While she'd sped up the rhythm, she was still slamming into me with each stroke, rocking me forward on the bed until my face was buried into the mattress and my back was arched, receiving each rocking impact with mounting pleasure. She was obviously enjoying it too, because she started to talk to me.

"You like that, you dirty slut?" she said, emphasizing 'slut' with a hard thrust. "You like my cock deep in your ass, huh?"

"Yes," I panted, rocking back to meet her. "Yes, I like your cock in me. Harder, deeper!" I squealed as she buried her dick deeper, gasping breathlessly.

"You're a nasty little butt-slut, aren't you?" she demanded. "Are you going to cum with my cock in your ass?"

"Yes, please," I said between gasps. It was true. Despite my earlier treat, I felt the sensation building up, and knew if she kept at it, I would definitely cum again. "Just don't stop fucking me!"

My plea spurred her on, and she increased her steady pace, rocking me into the bed until I could do nothing but gasp and moan and clutch at the sheet as waves of pleasure rocked through me. It continued to build and she could sense it by the way she found even more, fucking my ass savagely until I finally screamed as it ripped through me, and I felt my panties fill with my sticky cum, and I felt my mind drift away for a while.

She kept fucking me for a good minute afterward, as I slowly regained full consciousness. It was a gentler fucking now, and she stroked her hand across my lower back as she did it, murmuring softly, "good girl, that's my good girl." When I was recovered, she slowly slid the warm dildo out of my ass, leaving me with the delicious throbbing that always followed a good hard fucking. I rolled over and slipped a hand into my panties, scooping a finger through my cum and bringing it to my lips before giving her a smile.

"Well?" I asked her. "Was it everything you wanted?"

"It really was," she answered with a smile of her own. "I think I've officially found a new kink."