Half 21
I could not fall asleep straight away. Not surprisingly, I used to be sexually annoyed, however that wasn’t the one purpose sleep did not come. Holding Lily in my arms as she slept was additionally protecting me awake. I actually preferred this lady. She was humorous, sensible, horny, and we had various pursuits in frequent. I had an amazing night along with her. However, simply hours earlier I had been pegged by Tiffany, who I liked. I used to be conflicted and my thoughts wouldn’t let me ease into sleep. Finally my thoughts relaxed and sleep overtook me.
Some hours later I wakened with Lily wrapped round me nonetheless sleeping. With my free arm, I propped my head up and scanned her place. Within the fog of final evening’s buzz, I solely registered some fundamentals however now I might soak up extra.
Her place was strewn with garments – panties, bras, shorts, skirts, stockings, and sufficient footwear to open a retailer. Many of the clothes was boyish or gender impartial, which I used to be beginning to discover endearing. There was additionally a pile of books on the ground within the nook close to the futon. I couldn’t make out any of the titles, however they gave the impression to be largely paperback novels. There additionally gave the impression to be small stacks of comedian books scattered about. Though the place was positively cluttered, it did appear clear.
I feel my actions, regardless of being refined, have been sufficient to awaken Lily from her slumber. She stretched her legs and arched her again in a method that I might solely consider as feline. She then seemed up at me, smiled, after which scooted as much as kiss me.
“Good morning, horny.” she mentioned warmly.
I smiled again and requested “How did you sleep?”
“Oh, these two orgasms final evening have been so good, I really feel like they put me in a coma. What time is it?” She mentioned reaching for her telephone.
“It is nonetheless early.” she mentioned.
“Oh, rattling! Ha ha ha…” she exclaimed, nonetheless her telephone.
“What’s it?” I inquired.
She turned her telephone towards me and I might see an image of a really giant flaccid dick.
“I feel that Jason may be jealous of you. He despatched a dick pic saying how a lot he missed me.” she defined.
The expression on my face turned bitter. She dropped her telephone and jumped on me straddling my hips, and lowered her face to mine.
“Do not be that method! I might a lot reasonably be with you than him. His dick is fairly massive and as a lot as I loved it, he’s a bit little bit of an asshole. I by no means actually preferred him. I already such as you higher than him and he by no means made me cum the way in which you probably did final evening.” she inspired, leaning in for a kiss.
I put one hand on her decrease again and the opposite on her higher again and pulled her all the way down to me. We embraced that like that for some time kissing. She then broke the kiss and mentioned, “I feel I promised you pop-tarts, are you prepared?”
I shook my head sure and he or she bounced up and about, nonetheless nude, and made her method over to the kitchen. I watched her from the mattress as she ready espresso and put some pop-tarts within the toaster. After not too lengthy, she returned to the mattress with two mugs of espresso and a small plastic plate with 4 pop-tarts.
“Sorry, I’ve no cream or sugar right here since I drink it black.” she apologized.
“No downside, I can deal with a bit black espresso. Thanks for this connoisseur breakfast!” I mentioned with a smile.
She chuckled and we ate, drank, and chatted. Once we have been completed she cleaned every little thing up and he or she bounced again to the mattress and hopped in beside me. She cuddled up beside me and started kissing my chest.
In between little kisses she uttered fragments:
“So…”
– kiss –
“…I am questioning…”
– kiss –
“…did you…”
– kiss –
“…and Tiffany…”
– kiss –
“…use your…”
– kiss –
“…current buy…”
– kiss –
“…but?”
“Uuuh, yeah, she used it yesterday morning.” I answered.
She stopped kissing my chest and checked out me excitedly.
“Inform me about it, I would like particulars!” She insisted
I used to be a bit reluctant, however what is the massive deal I suppose. So, I began to inform her. I left off the bit about begging, I wasn’t positive what she may consider that, however in any other case I attempted to be detailed.
On the level I used to be telling her about kneeling in my room serving to Tiffany placed on the harness, Lily took my proper hand and pulled it to her pussy. She was very moist. Instinctively, I began to rub her clit, however I additionally had stopped speaking.
“Hold speaking and rubbing.” she mentioned.
So, I continued with my story and rubbing. I slid my fingers all the way down to moisten them, after which again as much as deal with her clit. She stared at me with lustful eyes as I spoke. I might inform she was getting shut. Nearly as if it have been timed, she started to tense up and shake as I used to be describing Tiffany’s orgasm from pegging. I finished speaking and we kissed for some time.
“That’s so fucking sizzling! I feel Tiffany is gorgeous and the concept of her fucking your ass is so horny!” She exclaimed.
“Have you ever ever pegged a man?” I requested.
“No, I’ve by no means pegged a man, however I’m no stranger to sporting and utilizing a strapon. Jessica, a pal with advantages, and I take turns utilizing strapons on one another.” she answered.
“Oh, what number of mates with advantages do you will have? Are all of them girls?” I requested.
“I’ve a couple of, and solely Jessica is a girl. The opposite two are guys. One older man that’s sort of a dominant mentor with me, I name him once I need it tough. The opposite man is a dumb school pupil with a pleasant dick and tons of stamina.” she answered.
I feel my face will need to have involuntarily given away my concern, as a result of she continued speaking “Dan! I do not need you to fret about any of that. First off, I do not actually like all of them as a lot as you. Additionally, I am not getting all jealous about your two sizzling keyholders. We have solely simply began to get to know one another. Hell, we have not even had intercourse but!” she jogged my memory with a smile “I wish to hold seeing you and get to know you higher. When the time comes to speak about exclusivity, we will fear about mates with advantages and who holds what keys.”
She paused and seemed me within the eyes. “Are we okay?” She made a pouty face.
I compelled fun and mentioned, “Certain. You are proper, I am sorry. I such as you too and I feel being locked makes me really feel a bit insecure.”
“I am tremendous excited that we’re seeing one another, and, I hope you may inform that I am down to search out out what turns into of this.” She paused, “Okay, sufficient of this critical discuss, I am hungry once more. I feel you need to deal with me to lunch.”
I used to be additionally hungry, so we obtained up. We took a bathe collectively in her tiny lavatory. She washed me down and I washed her. Periodically, we stopped to kiss and make out. We went to a neighborhood diner for lunch and had fun chatting and joking round.
We parted methods after lunch. I requested if she was free subsequent Saturday. She mentioned she was and would depart it free for one thing with me.
I walked dwelling elated. I had an amazing weekend and was trying ahead to seeing Tiffany on Monday. My balls ached, however I used to be comfortable.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~
Half 22
I used to be nonetheless in a superb temper Monday morning. The primary half of the work day flew by. Within the early afternoon I texted Tiffany and requested if I might see her. She mentioned she would come by and I used to be over the moon. It had been fairly some time since I got here and the final time was from a pegging with Caitlin. I actually needed to cum from stimulating my penis. I positively hoped for a handjob from Tiffany, however would accept the masturbation tube.
That night, once I met Tiffany on the door she was sporting a kind becoming darkish blue gown and matching pumps. Her hair was pulled again in a ponytail and he or she was grinning from ear to ear. We embraced and he or she then made her method over to the sofa.
I grabbed a few beers, gave her one and set the opposite on the ground. I stripped all the way down to nothing however my chastity cage and sat at her toes. I eliminated every of her pumps in flip and started rubbing her toes.
“Inform me about your date with Lily.” she began.
I instructed her about each little bit of my time with Lily. Tiffany listened intently with not a lot of an expression on her face. After I concluded she mentioned that she was comfortable that the weekend was so good.
“I’ve plans to fulfill up with Lily on Thursday for espresso. She and I’ve determined to fulfill up weekly to check notes in your relationship.” she continued.
“Okay… why is that mandatory?” I requested.
“Properly, I really feel accountable for you. And he or she appears to love the present association. Plus, I like her too.” Tiffany answered.
With a frown, I accepted her reply. I used to be not satisfied, however I knew arguing about it will be counterproductive.
Tiffany then requested me if I needed to ask something of her.
“It has been some time since I’ve cum and I am in fairly a little bit of discomfort. I hoped that perhaps you may… let me cum immediately?” I requested.
She pursed her lips ever so barely and mentioned, “Certain. Go get the tube, lube, cuffs, and towel.”
I excitedly obtained up and obtained every little thing wanted. I returned to the sofa and Tiffany took the cuffs and sure my arms behind my again. She set the tube within the sofa cushion after lubing it after which unlocked my chastity system.
However reasonably than taking her common place on the sofa above the tube, she stood beside me.
“I obtained a textual content whilst you have been getting every little thing and I’ve to return a name. I’ll make the decision out of your bed room whilst you maintain your wants. Do not wait, I may need to go proper after the decision.” she mentioned.
With that, she walked off to my bed room and shut the door. I did not transfer for a couple of moments as I used to be stunned. Earlier than lengthy, I spotted that I wanted to benefit from this chance for reduction, so I began to make use of the tube. After a couple of minutes, I got here within the tube and pulled out. I needed to proceed kneeling for fairly a while earlier than I might hear Tiffany come out.
“Did you end? I’m going to should run.” She mentioned as she approached me.
“Yeah, I am completed.” I responded.
She came visiting and wiped me down with the towel and reattached the chastity system. After she unlocked {the handcuffs}, she sat down and placed on her footwear.
“Is every little thing okay? Was it the decision?” I requested
“Yeah, every little thing is okay. Simply a difficulty at work. I am really going to have to move again there now.” She answered.
With virtually no ceremony she began towards the door. I adopted her, however she opened the door with no hug and simply turned barely and waved as she left.
One thing did not appear proper and I did not assume it was the decision. No, I am simply being paranoid, I instructed myself.
Regardless, I used to be crestfallen. The day had began so positively and ended on a hole be aware. Though my balls now not ached, I had a nagging feeling that one thing was improper and it was my fault.
I waited till the following day round 11am to textual content Tiffany. I requested her if work was okay. She did not reply till round 5pm. She mentioned that the shit had hit the fan and that her week was shaping as much as be hell. She added that she did not anticipate to have the ability to cease by for some time. I despatched again a tragic face and requested her to inform me if there was something I might do to assist.
For the remainder of the week, I texted her to test in and he or she would simply reply that issues have been nonetheless the identical. By Thursday morning I had resolved myself that I would not see her once more this week.
Though I used to be very disillusioned by my lack of interplay with Tiffany, I had been texting with Lily about Saturday. We have been planning to get dinner at one in every of my favourite locations after which off to a film that we have been each excited to see.
I finished texting Tiffany and tried to console myself that I used to be most likely not the rationale she was upset. I figured it will be higher to provide her a bit area and for me to deal with Lily.
I walked over to Lily’s place on Saturday and met her on the sidewalk. We took a experience share to an Indian place that I actually get pleasure from. We had a good time chatting and joking round. After dinner we walked to the theater. We obtained popcorn, chocolate coated raisins, licorice, and a big soda to share. We settled into our seats that have been the reclining kind. We have been fairly early and the previews hadn’t even began, so we sat and chatted.
After a bit pause in our usually fluid dialog, Lily requested me “So, I collect that earlier than being locked you were not actually into kink or BDSM. Now that you’ve got been uncovered to a few of it, do you discover it satisfying?”
“Hmm, sure and no. I am not so positive concerning the issues themselves. I suppose what I imply is that having my dick locked shouldn’t be what I might name enjoyable. It’s really fairly irritating. However, I discover myself actually turned on by how a lot you and Tiffany appear to get pleasure from it. Identical goes for pegging. I feel I could also be a bit extra into the foot stuff.” I answered.
“And what about being bossed round?” She requested with a smile.
“I do not know.” I mentioned smiling “I suppose it relies upon.”
“I feel I might really feel extra snug with my footwear off. Take them off for me.” She directed.
“As you would like, Lily.” I mentioned with a nod of my head.
I put my chair again right into a seated place and stood and moved to the entrance of her chair. I untied and eliminated every of her black converse in flip and positioned them on the ground between our chairs. She watched me intently consuming popcorn as I labored. There have been a couple of different folks within the theater at this level and the lights have been nonetheless shiny, so a few of them seemed. It was a bit embarrassing, however I did not care an excessive amount of. I sat again down in my chair and reclined it and turned my head to her.
“Good boy.” she mentioned with a smile and leaned in for a kiss.
After kissing for a bit, we pulled aside and I mentioned, “I may not like being bossed round the entire time, however I did like that.”
“Good, as a result of I felt a jolt if you began untying my shoe and I noticed the define of your cage by way of your pants. I wish to sit in your face so fucking unhealthy.” She completed with virtually a growl.
“We will go away if you’d like.” I provided.
She took a deep breath and instructed me that she will wait. She grabbed my hand with hers and squeezed tight, and leaned again in for an additional kiss. Round this time, the lights started to dim and the trailers began.
We directed our focus on the display screen. Often, I might really feel her gaze on me and I might have a look at her. Her stare was lustful and drew out an animalistic need in me. Then she would flip again to the display screen, and after lingering for a bit, I might have a look at the display screen too. We did this thrice earlier than she leaned in shut, kissed me and mentioned “subsequent time we watch a film, remind me to put on a skirt and no panties.”
“Fuck.” I whispered, “I am going to remind you.”
She kissed me once more and mentioned, “I will deal with this film and never my soaking moist pussy, I recommend you do the identical.”
After which she turned again to the display screen. The film began and I attempted to deal with the plot, however I simply saved her. She did stay targeted on the film; properly, her eyes remained on the display screen anyway. By the point the film was over, I felt frantic. I needed to strip her out of her garments and bury my face in pussy.
I had ordered a rideshare again to my place earlier than the credit even ended. When the lights got here again on, I obtained out of my chair, took her footwear one after the other and put them on her toes and laced them up. I grabbed her hand and began pulling her out of the theater.
“Woah, what’s taking place?! The place are we going?” She requested playfully.
“I would like you on my face proper now. We’re going again to my place.” I mentioned.
“Cease!” she exclaimed, “Do not forget, I am the boss!”
After a short pause, she mentioned with a smile “Now, let’s return to your house so I can sit in your face!”
After a comparatively brief journey that was punctuated by aggressive kissing and fondling that will need to have disgusted the rideshare driver, we have been at my place.
We stumbled into my house, undressing one another as we kissed our method to my bed room. I attempted to push her all the way down to the mattress however she resisted and as a substitute pushed me down. By this level I used to be already nude and he or she solely had her panties on. She stood on my mattress above me and took them off. She instructed me to place my arms above my head and he or she lowered her pussy to my mouth, by no means breaking eye contact. She leaned ahead and pinned my arms along with her arms, shifting most of her physique weight in that path. I used to be already licking her pussy after which she began to hump my face. She began gently however obtained extra aggressive in a short time. Earlier than lengthy, she was grunting and shuddering on high of me.
She shifted downward and collapsed on my chest and we kissed lazily.
“I wish to fuck you so badly.” I mentioned to her.
She smiled, “I feel you’ll, ultimately. Tiffany and I met for espresso on Thursday and mentioned a timeline. Once we get to a sure level, I’ll ask for the keys. Tiffany will give them to me to be used so long as I would like them. And when I’m completed, I’ll return them to her. And, ultimately, if we turn out to be critical, she’ll give them to me to carry.”
I wasn’t actually positive easy methods to react to this data. All I might handle at this level was to ask what can be the purpose the place she would ask for the keys.
“Properly, it’s a sure period of time and different elements. Sorry to be obscure, however I feel a part of that is that you simply belief the 2 of us. And though she is aggravated with you, I feel Tiffany has your finest pursuits at coronary heart.” She answered.
“She’s aggravated with me? What did she say?” I inquired.
“She did not get into particulars, so I do not know.” Lily answered.
She continued, “However in case you do wish to fuck me, there’s something I might wish to strive.”
“What?” I requested.
“You may have a minimum of two strapons right here, proper? Properly, I would like you to put on one and fuck me.” she answered.
I used to be a bit disillusioned at first, however figured it may be good to be on the opposite facet of a strapon, so I agreed.
I obtained the strapon and harness that Caitlin had used and made positive they have been clear. I put the harness on and had issue positioning the bottom of the dildo so it was snug. Finally, I had it ready that wasn’t terribly uncomfortable. Lily watched as I made the changes; her face appeared caught someplace between amusement and pleasure. I requested if she was prepared; in response she obtained onto all fours and arched her again. The look of her slender waist tapering out to her good ass and her pussy peeking out from between her thighs had me straining towards my plastic penis jail.
I obtained behind her and lined the pretend dick as much as her pussy and slowly pushed ahead. I noticed it slowly disappear. She set free a pant and a moan as I thrust all the way in which in. Her reactions have been turning me on much more, however I might really feel nothing however stress towards my decrease abdomen. It was an actual thoughts fuck to have intercourse with somebody in a method that was acquainted and pure, however with no sensation.
She appeared to get pleasure from my thrusts so I attempted to ensure I moved in a method that maximized her pleasure. Though the essential motion was pure, it took a while to get used to the shortage of sensation.
We modified positions a couple of instances, and ultimately she ended up on high. She was kissing me as she moved backwards and forwards on the dildo. Finally she got here and rested on high of me kissing.
“That was good! I perceive it’s most likely awkward for you, however we could have a while to follow. I am going to most likely be utilizing your face more often than not.” she mentioned.
She continued, “Let me do one thing for you. I might wish to rub your again. Flip over.”
I did as she requested and laid on my abdomen after eradicating the strapon harness. She sat on my ass; I might really feel her nonetheless damp pussy relaxation towards my cheeks. As she rubbed my again and shoulders I might really feel her pussy grind into my ass. It positively felt like she was humping my ass and I could not assist however take into consideration her pegging me. Though it was a activate to consider her pegging me, the again rub was superb! After a comparatively brief period of time, I handed out.