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I never paid attention to strap ons or dildos all that much, so a quick glance on line proved that I was in way over my head. Tim and I never discussed what his sister and he did, so I asked Olivia for help. To say she was excited would be a little bit of an understatement.

“Okay, I rounded up a few basic ones. Since you insisted on not getting carried away.” Olivia had eight on her bed.

“Thanks, so besides their shape what’s the difference?” I asked. Olivia was more than happy to explain how each of them were worn and used, as well as the perks or downsides they had. Sex had never been so boring.

Two of them peaked my interest, so with Olivia’s help and removing some of my clothes I tried the one with harness first. It had three straps and hugged my ass snugly, it included a set of balls and the prick was canine in shape with a small knot. Olivia made a jerking motion with her hand, and I reached down and gave it a try. Naturally I didn’t feel anything beyond the tug of the straps. “It is pretty comfortable, but not very exciting for me.”

“It will get the job done and let you be a little rougher than the others.” Olivia picked up one that didn’t need straps. “If you want to get off too, you are going to have to lose the undies and try this one. I really like this style myself.”

I un fastened the straps, set the toy on the bed and dropped my shorts. Olivia knew I had a vigina, she had just not seen it before. So she was rather interested and smiled as she watched me. “So what’s the little pump bulb for?”

Olivia handed me the toy and a little bottle of lube. “Don’t worry I cleaned all of them first. The bulb inflates the plug inside of you to help it stay in place.”

I put a little lube on the toy and inserted it as deep as it would go. I moaned slightly as I squeezed the bulb to inflate the plug. “That’s a new sensation.”

“It does take some getting used to.” Olivia smiled and got down on her knees in front of me. She took the bulb from my hand and gave it a couple quick squeezes, smiled when I moaned and then took the toy in her mouth.

This toy was also canine in shape with a knot even, and I could feel the toy shift and rub as she gave it a blow job. Sufficiently lubed, Olivia started jerking it off aggressively and my legs went a little weak. “Okay, okay I get it.”

Olivia chuckled and smiled up at me. “Are you sure you got it? I’d be happy to let you try it out a little more, maybe give you some pointers.”

I grinned sheepishly. “I think some pointers could be useful.”

Olivia was a big girl and I’ll admit I was glad she didn’t want to be on top and ride me. It did take a little to figure out how to move my hips for it to feel good for the two of us. I did manage to get myself and Olivia off, though I was exhausted after the one attempt. She did admit that it was a little weirder than she had imagined it would be with me. Also she encouraged me to use the toy by myself a little more, to get used to the way it works.

It was a little more than I wanted to spend, but Olivia said I could make payments for it, and since she was glad to give me a hands on demonstration I could get it at cost. It saved me about fifteen bucks. I was also told Tim enjoyed getting pegged and likely would let me pound his butt too.

I decided not to ask him about it right away, but did try it out in the shower the first chance I got. The water made jerking off the toy easy enough, and the noise did a good job covering up my quiet moans. It took me a few tries, but I did manage to get it figured out enough I could jerk it off and give myself an orgasm. That kind of brought a smile to my face as I lay on my bed looking down at the silicon prick pointing up to the ceiling after getting myself off.

If I wore it a little before doing anything, I found I could get off a little quicker. Really an enjoyable trial and error period for a week and a half; today I would give Darcy a little dick payback. She was doing the dishes and I think she had expected me to have gone to my room to change after I got home. Instead I just had my pants down long enough to get the toy in position and comfortable before pulling them back up.

She smiled as I came up behind her like she always does to me, and she was more than a little surprised to feel the fake cock pressed firmly between her butt cheeks. “Hey there handsome, something got you a little excited?”

“Your ass in a skirt always gets me a little excited.” I hugged her tightly and kissed her neck. “I also might have gotten a new toy for us to play with.”

Darcy’s smile grew and she turned around and she put her arms around me. “I noticed.”

We kissed and groped before heading to my room, as I had more lube than she did. As she looked up at me from her position kneeling in front of me pulling my pants and shorts down, she looked really sexy. Darcy didn’t mind blowing the toy, or giving it some firm jerks to make sure I was paying attention to her. She also gave the bulb a few good squeezes and smiled as it had gotten me to moan loudly.

She just kicked off her panties, got on all fours on my bed and hiked her tail up. “Don’t keep me waiting.”

I lubed up the toy and fingered her ass a little before getting on the bed behind her. Darcy moaned a little as I pushed the toy in her and she pushed back against me. The position took a little work for me to get figured out, but it wasn’t long before Darcy was moaning into the pillows while I fucked her ass with the toy, I had worked up a little bit of a sweat and shuttered as I climaxed before collapsing on top of her panting in her ear. “That was better than I had expected.”

“That was pretty intense. Did you?”

I kissed her cheek before rolling off of her. “I did, I think I like doing this.”

Darcy shifted so she could straddle me and plopped down on the toy. “I didn’t say you could be finished.”

She also inflated the toy a bit more before riding the toy to her own climax, shooting her load on my chest and on my face. I had a second orgasm and enjoyed the fact Darcy took the time to lick her cum off of my face and we kissed for a long time lying in each other’s arms.

That toy got quite a bit of use for a solid two weeks, including a few times in the shower and Tim let me peg him twice. I had a hell of a time swallowing his load the one time I sucked his dick while pegging him. I ended up with cum in an eye, up my nose and in one of my ears; he did apologize and helped me get cleaned up.

Not that I learned anything from that mistake as Darcy did the exact same thing. Except she slowly licked the cum off of me while fingering me, I came pretty hard. And while using the toy was enjoyable it didn’t compare to when I was bound, the helpless feeling that came from being tied up, to let Darcy or Tim have that much control nearly matched the drug she had used on me.

The mere suggestion of it would excite me, even just wearing the ropes not being bound and free to move aroused me. Tim had come over on one weekend to game and we did for a while until he and Darcy discovered I had been wearing the rope harness under the school girl uniform. They were not very subtle about hinting they wanted me to wear the uniform, and some more rope was rounded up to tie me up a little more. When they finally let me free it was hard to walk and I swallowed a fair amount of cum, as well as had it nearly everywhere.

I should point out that all of our interactions did not end with me getting fucked. Sex happened but was not a daily thing as we still had school and other things we had to take care of. School was winding down with only a few weeks left until summer break and that’s when I met Robin.

I was used to most of my classmates not liking the kind of music I enjoyed. So the snide comment about a band shirt didn’t really get me, but this one was oddly specific and belonged to an unfamiliar voice. “Their second album is over rated, their third one is simply better.”

I was going to say something snarky, but had looked up and noticed a skunk girl with the exact same band T shirt standing on the other side of the table I was sitting at. She was on the tall side, had several ear piercings and blue highlights in her dark black hair. She was smiling so I returned it. “Actually their fourth is my favorite. You must be the new girl.”

She rolled her eyes. “As small as this school is I shouldn’t be surprised with all the new girl crap. Call me Robin, and you have no idea how nice it is to meet someone with decent taste in music.”

“I’m John, pull up a chair.” The only class we shared was study hall, but it was nice to have someone to talk to about music that wasn’t country and she was a bit of a gamer as well. She even played the same MMO as Tim and I but was in a much larger guild. Robin made the last little stretch of school a lot more interesting.

“I don’t think I have ever seen you make a friend that quick before.” Darcy teased one evening at dinner.

I gave it some thought. “I guess you are right, someone who games and likes music that isn’t country in this town is rare.”

“She got under a few girl’s skin, well the clicky cunts anyways. Rumor says she is lesbian.” Darcy paused long enough to shove some food in her mouth before continuing without finishing chewing. “I suppose if it’s true that would be a good thing for you.”

“How would her being a lesbian help me?”

Darcy rolled her eyes and swallowed her food. “Did you forget you have a pussy?”

I sighed. “I think there is a little more to it than just having a vagina. You have the tits remember?”

“Yeah I know, but you actually have stuff in common with her, like that noise you insist is music.”

We sat in silence for a little while and I mulled it over. I did like Robin, probably the first girl I really liked that wasn’t my sister… That startled me a little bit, one that I was interested in another girl and two that Darcy wasn’t being defensively jealous. “Darcy, are you actually suggesting I maybe go after her?”

“Yeah. I’m kind of jealous some other girl caught your eye, but as much as I love what we have I know it can’t go on forever. The old me would be insanely jealous, but I think I could handle it if you had a real girlfriend.”

I smiled. “You really have changed, I still love you but the idea of being with Robin is kind of exciting.”