Goodbye Lily

After spending a couple of years with my roommate, Lily, I think I finally became comfortable around her. At first, I was a bit put off. My ex-roommate brought her in without my knowledge to take over her part of the rent when she left. I was stuck with her. Lily was far more open and frank, especially about matters of sex and masturbation. For part of the time, she sold sex toys out of our apartment. She would constantly talk about masturbation, and urge me to masturbate at times. She even gave me a vibratingprostate massager once. I’ve written about these experiences on here before.  But now, she was leaving.

Over time, I got comfortable enough that I was able to walk around the common area in just my underwear. I usually wear black bikini underwear, and for some reason, I was ashamed of them. I guess I got criticized by girlfriends too many times. Lily didn’t give me any shit about them. In fact, she said she preferred them over boxers.

I was drinking my morning coffee in my underpants while she was packing up the last of her things. What would I do without her?  Would I shut myself off again? Would I go back to being the same old buttoned-down, repressed guy? Or would I takesomething from our friendship? Be more daring and open, and unafraid to give myself pleasure?

“Well… I guess I’m off,” Lily said.  “I’ll drop my keys off at the office before I go.”

I gave her a hug. She wasn’t a pretty girl, but she had a nice little body.  I just realized that I was standing there in only a skimpy pair of underwear, hugging her—and her body felt nice.

She noticed the semi-boner in my underwear and giggled. “You can take care of that after I’m gone. You’ll have the house to yourself.”

I laughed. A couple years ago, I would have been mortified.

I walked her to the door, and we said our goodbyes.  It was a sad experience.

I didn’t act on her suggestion that I should have a wank.  I had to dress and get to work.

I got home to an empty apartment. What a strange feeling.  I went to change out of my work clothes. As I stood there in my briefs, I got to thinking about Lily. The last thing she said to me was that I should go jerk off. I decided that I would do it in her honor.

I remembered that I had taken a pair of her panties out of the laundry once. After what I did to them, she didn’t want them back. I had jacked off into them and threw them away, but there was something about them that gave me a boner. I fished them back out of my trashcan and washed them. They have been in my dresser drawer ever since.  I pulled off my briefs and put on Lily’s panties. I felt the lace and the satin bow on the front and my dick got instantly hard.I got the plastic bottle of lube that Lily had given me and went downstairs.  I poured myself a drink and flipped on the TV.  I put a porn DVD in the player.  A busty secretary was pulling down her boss’s pants. As she bent over, you could see her thong up her miniskirt.  I started feeling myself through the soft fabric of the panties.

As the secretary on the screen started bobbing her head up and down in the boss’s lap, the head of my penis peeped out of the thin elastic band, right by the pretty bow. I pulled my dick out of the panties and positioned the elastic under my ballsack. I lubed up the full length of my shaft, and even rubbed a little bit onto my balls.

Secretary and boss on the screen were both entirely naked now. He was on his back on the floor, and she was still sucking him off. I was slowly stroking up and down while watching. Then, unexpectedly, she started fingering his ass.  That gave meinspiration.  I took the bottle of lube and lubed up the middle finger on my left hand.  I arched up, put my feet on the coffee table, reached into my panties and pushed my finger into my butthole. 

I was fucking my ass with my finger (then 2 fingers) and stroking with my other hand. I had the apartment to myself, so I moaned as loud as the porn actors on the television did. I was really getting into it.

“Oh, sure.  Have all the fun AFTER I’m gone,” said a voice in the doorway. Lily was standing there, smirking. She had apparently come back to get something she had forgotten.

What a picture I must have been. There I was, feet up on the table,  two knuckles deep into my ass, lubed up and jacking while wearing her lacy panties and moaning loudly. On the screen the boss was railing the secretary from behind.

I guess I could have grabbed a pillow and covered up or run out of the room. But I was caught dead to rights.  I offered a weak smile and said… “Care to join me?”

She smiled. We had never masturbated together before in all the time we lived together. She walked in and started removing her pants. She gestured to the panties I had stolen from her. “They look good on you,” she said, humorously. “You should wear them more often.” My still-exposed penis hardened a little as she said this. 

She was wearing a black lace thong under her jeans, which also fell to the floor. She looked at the television. “Those boobs are fake,” she observed. I had no complaints about them.

She sat down in the recliner and drew her legs up. She pulled her little vibrator out of her purse.  I never knew her to ever be unprepared for masturbation.  She turned it on with a buzz and drew it down to her pussy. Using her fingers, she spread her vagina and worked the vibrator in on her clit. She motioned me to continue.  I sat down and started slowly stroking my cock.

“Uh uh,” she said. “That’s not what you were doing when I walked in.”

Well, she had already seen me fingering my ass, so I wasn’t going to get any more humiliated, I guess.  I propped my legs back up on the coffee and grabbed to reapply the lube.“Hey, where’s that vibrator I got you?” she asked.

I stopped.  “I wasn’t going to make this a big production,” I answered.

“You clearly were,” she said. “You even got dressed up for it,” she said, noting the panties. “I’ll pause the movie and you run and get it.”

The scene was over anyway, and it was a good stopping point.  Lily had paused the video at the exact point when the first shot of semen was hitting the secretary’s gigantic boobs. I didn’t argue with her. In fact, I was starting to feel like I might like a little more than my finger up there.  I pulled up the panties and went to my room to retrieve my vibrating prostate massager.

I came back down, and she started up the video. The boss was covering the secretary with his cum. I kicked off the panties and lubed up the vibrator. I reclined on the sofa with my legs up and carefully guided the toy into my anus.  I switched it on and selected a pulsing pattern. I grabbed my cock and started stroking again, watching Lily as she started working her vibrator.

The scene switched. It was now a couple of college students in a dorm room.  They were disrobing while he was occasionally sucking on a tit. Lily let out a sigh. “You can moan louder than that,” I teased her. “My roommate’s gone.” She started moaning louder… at first for comic effect, but then she was getting into it.

I stopped watching the video and started watching Lily. She was now fucking herself with the full length of the vibrator. She was now topless, and her free hand was feeling her breasts.  The vibrations were nailing my prostate and I was feeling good. I stoked faster with my right hand while cupping my balls with my left.

I was now writing on the couch. I was moaning again, along with Lily and the two tight-bodied students who were in the missionary position on the screen. Lily said, “Cum for me.” She pleaded.  I couldn’t hold it anymore.  My whole body tightened and I started shooting my load as the vibrations kept throbbing in my ass.  My chest and stomach were covered. This set Lily off. She screamed  and her body shook. We both got what we needed.

“We should have done that a long time ago,” said Lily.

I stood up and wiped off my chest. She came over and embraced me.

Goodbye Lily.