A few years ago when I first moved to Toronto I did some online dating. I was in my thirties and looking for something casual in a relationship. Not that I would have been averse to anything serious developing, but that really wasn’t what I had in mind.

Of course, the term ’casual relationship’ can mean different things to different people. It could mean anything from friendship to hooking up. For those in the latter group, the term casual relationship certainly offered a gentler means of proposal. It allows for the inclusion of those who wish to be a little more demure about their intentions as well as some who might just need a little convincing.

One girl I met who fell into the category of needing convincing was Rose. Rose was twenty-two years old, 5’ 3” and petite. She had straight black hair to her shoulders and a cute face with a little dimpled cheek. She was of Chinese heritage and grew up in Newfoundland of all places. Her origins in itself made her curiously amusing, because Newfoundland is no immigration hotbed. A beautiful, but a traditionally economically depressed region of Canada, the expectation is usually for people to leave the province, not move there. Nonetheless, that’s where her parents ended up, moving there when she was just a baby.

Like most Newfoundlanders, Rose had an adorable regional accent. Even though it was natural considering where she grew up, it was a mismatch with her ethnicity. Such combinations can sometimes seem a little funny and this one seemed funnier than most. Particularly because a Newfie accent is already considered amusing on its own.

For those unfamiliar, the province is the brunt of many a joke. Though most of them are likely authored by the island inhabitants. Whatever the actual merit of the Newfie intellectual reputation, Rose seemed to confirm the cultural stereotype. She was bubbly and much more innocent than I would have expected of someone her age. One way that she seemed innocent was a rather childish view of what she was looking for from the dating site. She was just hoping to meet new friends and her experience with men seemed virtually Amish.

Rose was a virgin and considering what I was looking for I should have crossed her off my list. There was something about her though that made me want to meet her. Her innocence made her seem younger than her actual age and her experience with men was non-existent. While she was sheepish about it, she had a curious willingness to discuss some sexual topics. Amazingly after a couple of conversations, I managed to convince her to meet.

I’d developed a bit of a formula for my online dates. Meet near my place and have a couple drinks. If there was chemistry, invite my date home for another drink. Step one was in place, but it turned out that Rose never drank anything stronger than coffee. In my mind this didn’t bode well. I assumed a virgin would need something to loosen her inhibitions. Surprisingly just about when we seemed to run out of things to say, Rose willingly accepted my invitation.

Back at my place we sat on my couch and chatted. Given her unblemished history, I wasn’t expecting any success seducing Rose, but there was no reason to not at least try. I kept steering the conversation in suggestive directions. While Rose never parried away any topic, her reactions didn’t delineate a sexual topic from anything else we talked about. Everything was treated with the same level of happy, but unaffected enthusiasm.

Eventually, I began to run out of conversation again and sensed the date winding down. With no real lead up and with nothing to lose, I asked Rose if she would like a massage.

“Okay sure,” she replied.

Surprised that my cheesy suggestion was accepted, I moved to the edge of the couch to make room. “Here, you can lie on your stomach?”

“Alright,” Rose agreed.

I helped orient her body and gently began the massage. From her shoulders, I slowly worked down her back. My progress was almost immeasurably gradual. Without being too bold I traversed Rose’s hips, massaged down her legs and back up. I massaged her inner thighs and sweet little bum, avoiding any overly erogenous points. Returning to Rose’s back I let my hands slide under her sweater. Kneading her skin directly my massage worked up Rose’s back again.

The expanse of my massage continued to grow. When I returned to Rose’s legs I spent more time squeezing her glutes and rubbing suggestively between her legs. From her back, my hands flanked Rose’s torso and moved under her body. Gently my hands found their way under her bra, finding soft territory that could no longer be considered innocent. Without resistance I gathered Rose’s breasts in my hands. When my fingertips touched her nipples, Rose stiffened like a kitten stretching. Releasing a deep breath her body relaxed again as she passively accepted my touch.

Rose’s breasts were getting me understandably horny. I hadn’t expected anything to happen with her, so to keep from breaking the mood I took things nice and slow. Her skin was smooth and her nipples excitingly supple. I wanted to have them in my mouth, but that seemed too bold. Wondering if Rose would notice I brought my fingers to my mouth to dampen them. The warm spit covering my fingers made Rose’s nipples feel slick as I massaged them. Repeating the technique, I applied more spit each time. While perhaps not the body fluid I would have preferred, it was enough to make it undeniable that the massage was now overtly sexual.

I eased Rose over on her back. Pushing her sweater and bra up I kissed up her sleek belly to her modest breasts. I nibbled my way up one of Rose’s tits and took a dark nipple in my mouth. For the first time, an audible moan escaped from Rose. Somewhat in disbelief, I kissed and sucked Rose’s tits, hoping the spell wouldn’t break.

With no sign of resistance, I eventually ran my tongue down Rose’s stomach, darting into her belly button. As my mouth moved to the top of Rose’s jeans my hand tentatively unbuttoned her pants and drew down her zipper.

Rose shifted slightly, but otherwise remained passively reclined on the couch. I kissed down to her underwear and used my index finger to draw down her waistband exposing a little black thatch. Burying my face in her prickly hair I began to pick up her sweet scent. My mouth could go no lower with her pants on. I was so close, but her taste was just out of reach.

I slid my hand inside Rose’s underwear and touched her lips. I could feel my breath running through my finger heating Rose’s damp pussy. I tried to slide my finger inside her, but even with her pants undone, it was still too tight to allow much movement. Fortunately, Rose arched her back allowing me to slide her jeans over her hips. With her pants down to her knees, I was able to get my head between her legs. Taking advantage, I ran my tongue over Rose’s clit and across her wet pussy making her shudder.

I'd probably been massaging Rose for almost an hour to get to this point. Now that I had her where I wanted, I planned on taking as much time as possible. The only restriction was Rose’s pants, bunched around her knees. It meant I could only spread her legs so wide. My tongue could lightly taste her, but I couldn’t bury my face in her honey pot. Once I felt confident that there was no turning back, I paused to pull off her pants. Helping, Rose kicked to free her feet and spread her legs apart to welcome me back.

Kneeling on the floor between Rose’s legs I began an indulgent feast. Rose’s moans were hushed, but luscious. They hung in the air melting. When my tongue slid across to her untouched asshole, there was no marked difference in her reactions, only continued satisfaction.

I licked and fingered Rose’s pussy and ass through building waves of orgasm. Finishing by sucking her clit with two fingers fucking her ass. Her body shook as her pussy gushed in my mouth with surprising wetness.

I continued to lick her until her body stilled. She seemed satisfied and drained, which certainly made me feel like mission accomplished. In truth, even though I had an unrequited hard on, I felt a bit tired myself. The underside of my tongue felt the stretch and strain of its marathon efforts too. But as they say, it was a good kind of pain.

Sitting back up on the couch, I could feel her pussy juice drying on my face as we chatted.

“That was a bit of a surprise,” I commented.

“Yeah, I really don’t usually do things like that,” Rose professed.

I’d heard claims like that before, but in Rose’s case I didn’t doubt she was being honest. Still, I was curious and asked, “Have you ever had a guy go down on you before?”

“You mean like what you did? Yeah, once or twice,” she admitted. Then added, “It was a while ago.”

“Did you meet him online too?”

“No, he was a friend. We used to hang out together.”

“Why’d you stop?” I asked.

“I don’t know. I’m not really sure how it even happened. I think we were just playing or something.”

“Did he ever lick your ass the way I did?” I asked.

“No, I don’t think so.”

“Did you like that?”

“Yeah, it was nice,” she bashfully giggled.

As we continued to talk, Rose surprised me with a question, “Would you like me to do you too?”

While I hadn’t expected to be able to get Rose naked on the couch, I’ve always appreciated that people can be swayed by the right stimulation. However, as the afterglow faded, I would have been less shocked by expressions of regret than offers of reciprocity.

“Sure!” I agreed. “That would be great.”

I butted out my cigarette and leaned back on the couch to give Rose access.

“Okay, here goes,” Rose said with a flustered chuckle. She leaned over and touched the evident bulge in my pants before pulling down my zipper. Becoming a little more serious as she tried to root out my cock, her sheepish grin gave way to a focused look.

After a bit of ineffectual struggle Rose asked, “I’m afraid I’ll hurt you. Can you take it out for me?”

I’ve always enjoyed when a girl struggled to take out my cock. It feels nice to have someone willing to do a little work to get access. Since Rose was having so much difficulty though, I figured it was worthwhile to give her a little help. All I had to do was undo my belt. With my dick already sticking out above my underwear’s waistband it sprang upright for Rose.

“Oooh!!” she cheered as my cock bolted free.

I lifted my hips and slid my pants down to give her unrestricted access. Rose took my hard cock in her hand and started tentatively stroking my shaft. Her light touch felt nice, but as time passed it didn’t progress. Her grip was loose and her hand moved slowly. As preliminary stimulation it was fine, but it never would have made me cum.

“Try squeezing a little tighter,” I advised.

“Won’t it hurt? Rose asked.

”No, but if it does I’ll let you know,“ I assured her.

Gripping just a little more firmly Rose continued her mild hand job.

”Tighter and a little faster,“ I again urged.

”Really? Are you sure I won’t hurt it?“

”I’m sure.“

”But I thought guys were sensitive down there?“ Rose added, still looking for assurance.

"If you were squeezing my balls it would hurt, but cocks can take a lot of abuse.” Then I added, “If it couldn’t take more pressure, guys wouldn’t be able to put their cocks inside girls. So not only doesn’t it hurt, it’s actually about the best feeling a cock can have. Guys spend a lot of time and effort trying to get our cocks squeezed just like that.”

Somewhat reassured, Rose gripped me tighter, but it was still a pretty tentative effort. To give her a better idea I took her hand in mine, squeezed tightly and began pumping my cock.

“I can’t believe that doesn’t hurt,” Rose exclaimed.

Rose went back to stroking my cock with the tightest grip she could manage. Showing better purpose, she increased the speed and force of her hand along my shaft. It was really beginning to feel quite good and I particularly enjoyed the earnest look on Rose’s face as she studied her work.

Every so often Rose would change hands as her wrist grew tired from its work. To help I guided her unused hand to my balls.

“You can be gentle with these,” I reminded her.

Rose’s hand switching increased as her fatigue grew. Since I wasn’t quite there yet and I wanted to give her a chance to get me there on her own I took a moment to kick off my pants.

“Why don’t you try getting down on the floor between my knees?” I suggested. “Then you can play with my ass like I did with you.”

“Alright,” Rose agreed.

She got down between my knees and I was hoping she might surprise me again by licking my ass. Considering she’d not even tried to kiss my cock, let along suck it, this was a real long shot. I was still satisfied when her finger began working its way inside my ass, but it did feel a little pinchy. Since Rose still hadn’t put her pants on, I suggested she use her pussy juice to lube up her fingers.

“Will that help?” she asked with wide eyes.

“Can’t hurt,” I estimated.

Dutifully Rose took a couple moments to plum her nectar resources, then returned a finger to my back door. With greater ease her finger worked its way up my ass. I could feel my ass contract around Rose’s knuckles as she went back to milking my cock.

Rose’s finger in my ass was really doing the trick. It felt incredible and it was a real turn on that Rose was so willing to do it. Meanwhile, her other hand pumped my cock with its newly coached grip. Looking down I could see her face in concentration right behind my cock. She was so close to it, that I was imagining splashing her cute face with my load.

Rose had to switch her hand a couple more times, always freshening her fingers with pussy juice to work up my ass. When she went back to pumping me with her right hand she got me so close. I could sense her hand getting tired again and I just couldn’t wait any longer. Before she could stop I grabbed her hand and began guiding it up and down my cock at a finishing pace.

“Oh yeah, deeper!” I cried.

As I reached the point of no return I could feel my asshole tighten around Rose’s finger. Even at the onset of orgasm, I was still lucid enough to angle my cock towards Rose. The first shot was too powerful and arched over her head. The second shot landed in her hair and on her cheek.

“Hey!” she cried recoiling back.

I continued pumping my cock with Rose’s hand. I slowed the pace, but made increasingly long strokes to fully milk my full load. My sperm flowed out, running down my cock over both our hands. When I let go, Rose continued to run her hand up and down my shaft.

“Why does it feel cold?” she asked of my sperm.

I’d never really given much thought to the temperature of cum before. I’d always thought of sex and the associated body fluids as hot. In dirty talk, sperm's always hot. Rose was right though, it did feel cool. After all, there’s a reason testicles are outside the body and not inside. It’s to keep the sperm factories below body temperatures for optimal productive conditions.

After I explained it to her, Rose began clinically feeling the sperm covering my cock and playing with it. She stretched it between her fingers and rubbed it into our skin. She even leaned over to take in the scent.

“Would you like to try a taste?” I asked.

“No way! I could get pregnant!”

“What??”

“If I swallow any I could get pregnant,” Rose warned.

“Are you serious?” I asked.

“Well yeah, you can get pregnant that way can’t you?” Rose asked.

“Really? Don’t they teach sex education in Newfoundland?” I asked in disbelief.

“I guess they do. Maybe I wasn’t really paying attention,” she laughed.

“Well, the answer is no. You can’t get pregnant by giving a blowjob or swallowing sperm. The only way to get pregnant is by fucking,” I explained.

“Are you just saying that, so I’ll taste your cum?” Rose suggested.

“Well, I would like to see you do that, but I’m not trying to trick you into it. There’s zero chance of getting pregnant, but only do it if it’s something you want to try.”

“I thought it didn’t matter how sperm got into your body?” Rose asked as she began to waver.

“No, you can swallow all the sperm you want. Honest. The only way to get pregnant is if the sperm is in your pussy.”

“Okay I’ll try, but I better not get pregnant.”

Since I wasn’t even asking Rose to taste my sperm, I was again exceptionally pleased by the turn of events. Rose held her sperm covered hand up to her mouth and took another sniff before sticking out her tongue for a taste. She tentatively dabbed a splash of cum on her wrist against her tongue. She made a bit of a sour face before going back and licking off the cloudy glob of sperm.

“It’s kind of different tasting. The taste isn’t that bad, but it’s so pasty,” she said smacking her lips with a look that didn’t seem entirely pleased.

“I think it’s an acquired taste,” I suggested.

Trying one more sample Rose licked the final flow of the head of my cock.

“Maybe you’re right that one seemed better.” But then added, “Could I have a glass of water?”

I filled up a glass in the kitchen and when I returned I found Rose had already helped herself to the Kleenex box on the table to clean up. Realizing this meant she likely wasn’t going to lick my cock clean, I gave her the water and grabbed some tissues for myself.

We sat back on the couch and talked a bit more. We discussed the surprise of the night’s events and made plans for another get-together. I even suggested that if she wanted to know what it was like to be fucked without losing her virginity that we could try anal. After all, she liked having her ass licked and fingered. Rose’s only reservation was her concern that she could get pregnant.