Roommate Gives Me a Gift, of Sorts

It took a little getting used to Lily as a roommate. A former roommate stuck me with her, and she was a little different. A free spirit. But after a few months living together, I became somewhat comfortable with her. But when I got home one night from my work, I was not prepared for what I saw. I walked in the door and I heard the giggles of several women.  I looked into the livingroom, and there, sitting on the couch, the loveseat, the chair and the floor, were a group of females.  I said, "Sorry, I didn't mean to interrupt", I said. This was followed by more giggles.  I looked on the coffee table, and I was stunned to see a huge array of sex toys of various sizes and colors. There were dildoes, vibrators, and colored plastic devices of every kind.  Lily was hosting one of those parties. I didn't know that she had become a host for this line of products. She would later tell me that she did it for the discount. I knew she was an avid masturbator. She was frank in talking about it (to my great discomfort).  I often found her toys sitting out on the counter, or in the sink to be cleaned. I frequently heard a low buzz or a soft moan coming from her room.  Don't get me wrong.  I masturbated constantly at the time.  I tended to be more private about it.  More ashamed? At first I was always worried that Lily would hear me. But Lily was not just a practitioner of masturbation, she was also an advocate. (As I have mentioned in my other stories about her). She truly believed in the health benefits of masturbation, and at times, she would encourage me to go work one out.  As time went on, I didn't care as much about being overheard, and in fact, I felt comfortable moaning lowly from time to time. Yeah, it was weird. Well, anyway, I left the ladies to it, and I went upstairs to study in my bedroom.  I could overhear the women discussing this or that toy.  Lily knew the ins and outs of all the demo toys, and she explained them to her avid crowd.  This one made her feel full and satisfied. This one was exciting.  This one was the old reliable.  A rep from the toy company was there, and she answered questions, but I don't think that even she was as knowledgeable as Lily. The women talked about their favorites.  I've got to say, I was getting a little hard listening to them talk about their sex toys. I had a quick, quiet wank, not wanting to be overheard. Eventually, the crowd dispersed. They put in their orders, said their goodbyes, and left the apartment. I went downstairs to see if Lily needed help straightening up.  I helped carry in the dishes and throwing away the trash. Lily was excited. She had made several sales. But she was really happy about her new toys. The sales rep. allowed her to keep a couple of the demos.  To my chagrin, she showed me a rabbit vibrator, a glass dildo and some nipple clamps.  She held these out proudly as if it were the prize winning bass at a fishing tournament.  "Nice", I said, unenthusiastically as I rinsed out a bowl. "Oh, and I saved something for you, too!" Her excitement could not be contained.  She thrust a black device into my hand.  "It's a prostate massager!" "Uh, thanks?" I offered, staring at it puzzlingly. It was black rubber with a chrome panel and two buttons on it. It was bent at a right angle, and the business end had a couple bulges and bumps on it. While I was holding it, Lily pushed the button and it started to vibrate.  "This button turns it on, and sets the intensity". She pushed the button a few more times and the buzz got stronger and more powerful. "This button controls the pattern".  The massager switched from a constant vibration to pulses.  "There are 6 different and exciting patterns!" She was still in sales mode.  "Prostate massage is therapeutic", she lectured. "Not only is it good for your prostate and your reproductive health, but it feels really good, and promotes sexual wellbeing".  "Ok, Thanks". I said. Trying to sound positive. "Well, you going to try it?", she implored? "Not right now". I said. "Maybe sometime".  She looked disappointed. The next few times I saw her, she would always ask, "Well, did you try your massager yet?" And she would always be disappointed when I said no. She really thought she was doing me a favor, and she couldn't wait to hear about it.  To me, it was as if she had told me to shove it up my ass. Which I suppose was the case. One morning, as I was getting ready to shower, I looked at it sitting on my book shelf.  I was going to take a quick wank in the shower anyway, so I decided "What the hell?"  I got the lube she had given me, and greased up the toy.  I went to slide it in, and found that it was not going in easily.  I applied a little more force.  It hurt a lot.  I didn't even get it half in, and I took it out, washed it off, and threw it to the side.   That night, the question came again. "Did you try your toy"?  I was sick of the questioning, so I answered.  "Yes, I tried it.  It hurt. It was too big. I couldn't get it in.  I don't think it's for me". 

She frowned. "You can't just force it in, you know.  You have to set some time aside.  Relax.  You have to get your anus to relax and accept the toy. You'll hurt yourself if you try to hurry".  I tried to change the subject, but she wasn't hearing it.  "Go on upstairs now." she ordered. "Go strip down and relax.  Put some lube on your finger, and play with your anus for a while.  Once you can comfortably slide your finger in and out, then gradually work the massager in and out until you can get it all the way in.". She instructed.  

I protested, but she wouldn't listen.  She pulled me up off the couch.  "Go on. Go on. You're going to thank me one day".  I grudgingly went upstairs and closed the door.  I looked at the toy and sighed. I kicked off my shoes, took off my pants, my shirt and my bikini briefs, and lay down on the bed. "Take it slow. OK", I said. I breathed deeply and closed my eyes. I laid down on the bed, and relaxed.  I tugged my dick a couple of times and felt my balls. I reached behind me and caressed my buttocks. I circled the tip of my finger around my butthole. It felt good. I sometimes played with my ass while I masturbated, but very rarely. I stuck my fingertip just inside the ring and moved it in a gentle circle. I took out the lube that Lily gave me and applied some to my finger. "Contains vitamin E", she told me, "Good for your skin". I was glad that my butthole skin would be treated so well.  Here goes.   I worked my lubed finger around the rim, applying the goo to my anus. I rubbed at the hole, stimulating it. I was relaxing, breathing deeply. I pushed the tip in again. Man, it was tight! I really didn't think I would fit the whole toy in there. But I kept rubbing and circling. I took it slow. Soon enough, my finger went in. I pushed it deeper until gradually it was all the way into my butt. I drew it out a bit and slid it back in. I had forgotten how good this felt.  Pretty soon, I was able to fuck myself with my finger. I switched to the middle finger to get further in. I felt around for the prostate. Glossed over it as well as I could with my own hand.  I was now comfortably fucking my ass with my middle finger. I was making circles and patterns in there to prepare for the toy. As far as I was concerned, though, the finger felt good enough. I warmed up the toy with my hands. I covered it with lube. I turned over on my side, and drew my legs up a bit. I took the vibrator around and put the tip to my hole. It was big. I was doubtful.  I pushed a bit and pulled out. It only impacted the outside. I budged it gently again. This time the ring gave way, but it was still super tight.  I slowly reversed it, but I didn't take it out. I began moving it in and out. Each push took the toy further into me. Finally I was over the first "bump"... what would have been the penis head if it had been a penis. I didn't like to think about it as a penis, though. Now there was another bump to get over. Gradually, my anus opened to allow the massager in, as it glided up to the thickest point. It was a bit uncomfortable, but one more push and the massager slid into place- with just the handle sticking out.  A few more deep breaths. It was in, and it was comfortable. I had a feeling of being "filled up". It was somewhat satisfying. I reached for the button, and turned it on.  zzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzzz Oh, did it feel good, vibrating against my little walnut gland. I carefully turned over onto my back, pulled my feet closer so my knees were up, and titled the pelvis so I wouldn't be sitting on the massager.  Ohhh, this was good. I decided to try another setting. This one was an intermittent pulse. zzzz    zzzz    zzzz   zzzz    zzzz Nice.  Then a hill and valley pattern:  ..zzzZZZzzz...zzzZZZzzz...zzzZZZzzz... and then a saw-tooth pattern: ...zzzZZZ...zzzZZZ...zzzZZZ  This was my favorite, so after sampling all of the patters, I went back to this one.  My prostate was pleased. My anus was stimulated. This was great. It was weird to me that my dick wasn't fully erect. It was swollen a bit, but just laying flat against my belly, as if to stay low-key so that my anus could enjoy the spotlight for a change.  I noticed the clear prostate fluid leaking from the tip of my dick and forming little puddles on my stomach. I dragged a finger through the viscous, slippery liquid. It was strange for me to think it, but I had to admit that my ass was hungry, and it wanted more.  I fumbled for the intensity button and turned it up to 11.   WOW! Did I say that out loud? I heard a quiet laugh from downstairs. Did Lily hear me? I didn't care. This was hitting me square on the prostate, and I was loving it. BUZZ BUZZ BUZZ BUZZ BUZZ. I reached down for my cock now.  I was treating myself, so I didn't stroke it dry today. I covered the head and shaft with the Vitamin E lube. I put a layer of lube on the balls as well.  I started slowly stroking my cock while the massager pleased my ass. I cupped my balls and played with them liesurely.  My naked body wriggled on the bed. My dick became hard and pointed straight up to the ceiling. The sensation was overwhelming.  I let go of my balls and reached down to the massager.  I pushed it up against my butt so that the shaft would go deeper. I was jacking and jacking, and pushing and pushing. I didn't care about Lily hearing me any more. I moaned lustfully.  Finally I couldn't take it anymore. I came hard and in buckets. This was more cum than I ever produced just by jacking off. If I had been standing in the shower during this orgasm, I likely would have passed out. "Wow", I said again.  I carefully extracted my massager and placed it next to me on the table. I laid my legs flat on the bed. This had exhausted me. I didn't even bother to clean up. My head was spinning, and my body was spent. I relaxed, naked on the bed, my belly covered in cum. Eventually, I regained some strength, and cleaned off. I put on my clothes, put the massager in the bathroom to be cleaned later. On still-wobbly legs I went downstairs.  Lily had a naughty grin on her face. "Well? How was it?", she asked. "Alright", I said.  I was still uncomfortable talking about masturbation with her. Nonetheless, the smile on my face and the noises I had made upstairs told her all she needed to know. I didn't use the massager regularly after that time, but I did put it carefully away, and took it out at times when I wanted special treatment. A few months later, she hosted another party.  I went up to my room again to get out of their way.  What would I do for a couple hours to pass the time?  I looked at the little toy in my desk drawer.  "Looks like a special night",  I thought, locking the bedroom door and pulling down my pants. As I was working in the massager, I could faintly hear Lily telling her friends, "This is Pete's little favorite. It always puts a smile on his face". The women giggled.  I'm going to have to talk to her about not using me as an example.