One Year Internship Ch. 16 – Wk 35

She put her next outfit on and then twirled around for me to look at her. This one was much more fitting for the occasion. I gave her my opinion, "I like this one better. I think you should go with something as minimalist as possible, and this one is getting much closer."

She approached me and commented, "Of course this one is more minimalist. There is nothing covering my nipples."

I noticed that immediately but was trying not to gaze. The bra portion of this set had only the bottom underwire to push up her breasts but did not have the fabric covering the nipples. Now that her exposed nipples were only a couple inches from my face, my defenses came crashing down.

As she pushed her left breast into my mouth, she commented, "If I want Brad to suck on my nipples, this would be a good option, don't you think Megan?"

As I started to make love to her nipple with my mouth, I could only moan my agreement. I grabbed her bare ass and pulled her in even tighter and moved to the other nipple. After a few moments, and several moans from both of us, Shana used all of her strength to pull herself away from me.

"Now now Megan. We have a few more outfits to try on. Behave yourself."

I could not help but let out a huff. I was behaving myself until she presented her sexy naked body to me. I reminded myself to take a few deep breaths while Shana took off this latest outfit. She turned and bent over again, teasing me. It was shorter this time, thank goodness.

This outfit took longer to pull on as it was somewhat of a full body suit. It fit her like a glove and its most appealing feature was that it was crotchless. My mouth watered and my pussy tingled as she brought herself within my reach. I did not wait for her to push herself into me and instead I was the aggressor, pulling her over to me.

She had just started to open her mouth to say something when I slid my hand over her pussy and slightly into her seam. She was sopping wet and accepted two of my digits easily. She moaned out load as I squeezed her body and fingered her pussy.

This was only momentary, before Shana begged me to lick her pussy. Even though I knew it was not appropriate for the time or place, I could not resist her. I pushed her back slightly and dropped to my knees on the floor. My mouth was on her wetness in a flash.

As I licked and sucked her, I was in heaven. I was so turned on by the texture of her pussy, the taste of her juices, and the sounds of her pleasure. I completely forgot that we were in a department dressing room and started moaning along with her.

When she climaxed, she groaned loud enough that the whole store probably heard her. I had just finished cleaning up her excretions when the salesclerk knocked on the door and commented that we had been in the fitting room for a long time.

Shana giggled and replied, "I have one more outfit and then I will be right out."

We could hear the salesclerk leave and Shana leaned down and kissed me. She laughed as she chided me, "Megan, you are a bad girl. You almost got us in trouble."

Her laughter got louder as she started to peel off the body suit. Shana controlled herself better as she quickly powered through the final couple outfits. She settled on a very skimpy lavender set, where the bra was sheer enough to see her nipples through and the thong was so tiny, it left little to the imagination.

We left the fitting room and headed to the cashier, where Shana bought her date night set, the original white lacy set, and the body suit. 'For later,' she commented with a wink. The lady kept glaring at us with the 'I know what you were doing in there,' glare. We just smiled and Shana paid for her lingerie.

As we left the store, we started laughing all out. On our way to the car, Shana commented that she enjoyed being out and about with me. We sat in her car, ready to transition to lunch when Shana looked at me with a slightly serious look.

"What?" I asked.

"I want to have fun. I want to experiment and try things and have experiences. I am not ready to settle down, and get married, and have kids."

She started the car and began to leave the parking lot. I replied, "I think that is great. Not to get deep really quick, but I do not know what that means for Brad or for me."

Shana got on the main highway and responded, "I am going to tell him tonight, Megan."

"You're going to tell him what tonight?"

"I am going to go to dinner. We are going to be loving and wonderful. I am going to explain to him that I want more adventure in my life. He is going to ask me what that means. I am going to tell him that I have a surprise for him when we get home."

I was still a little worried. All of the possible bad outcomes were flowing through my brain at that moment.

She continued, "When we get home, I am going to seduce him. I am going to suck his cock and get him hard and ride him for a little while and then I am going to surprise him. I am going to climb off of him and get into a deep doggystyle position and tell him to fuck my ass."

There was a moment of silence while Shana drove, and I thought. I could see her playing out the evening in her brain at that moment. Her expressions shifted every few seconds.

Finally, I broke the silence. "Shana. Is that it?"

She looked at me and replied, "No. I am going to tell him about us."

A flood of emotion nearly overcame me. While I knew this was a possibility someday. Today, it was real. "Why?" I asked.

"I share the same concern that you have Megan. I am not typically one who keeps secrets from my loved ones, especially ones as big as you and I. After Brad and I are finished with sex, and we are sitting in that loving afterglow, I am going to tell him that I am interested in being more adventurous and want him to do it with me."

"Okay?" I commented, still concerned.

"I am going to express to him that it has been on my mind for a long time, but I have always had trouble acting on it. Then I am going to tell him that I have been spending time with you. He knows who you are by the way."

"He knows my role, what I do?"

"Not exactly. He knows that you are in a high stress, high impact position, where you support the executives and that you and I work together."

"Okay."

We pulled into a parking lot of a restaurant, and she parked and turned off the car. She looked at me intently and said, "Then I am going to tell him that you and I have become intimate and that it has happened more than once. Then depending upon his reaction, I will explore what is next for he and I."

I was overflowing with concern right about now. I asked, "What if he gets upset and says you cheated and that he does not want to be with you?"

There was a long pause while she considered her words. She came back to the present and looked into my eyes. "Megan, would you consider being in a relationship with Brad and me? Like a regular threesome?"

I was taken back by her question. I fumbled around before coming to some coherent answer. "Uhh, I guess. I mean there are a million questions and conditions that come with that."

Shana took my hand in hers and maintained her attention on me. "Megan, I have come to a decision. You totally do not have to answer today. But I want to be with you when your internship is over, and I would like for you to think about it."

"What does that mean for tonight?"

"I am going to have a wonderful anniversary night with Brad, and we will see what he wants to do. My ideal ending to this story is that Brad and I stay together and that you join our relationship. And the three of us can do some fun things like have a threesome all the time and maybe a foursome or more at some point. We will see."

Shana shook my hand to add some intensity to what she was saying.

"I want to have fun going forward and do all the things that I have wanted to do, and I want to do them with you!"

My mind was racing. What did I want? Did I want what she just described? I was so confused.

Shana leaned over to me and kissed me. It broke me out of my trance. The kiss was nice and sensual. When she pulled away, she commented, "I love you, Megan. I want to be with you, even at the expense of my relationship with Brad. Like I said, you do not have to say anything or make any decisions tonight. Let's go have lunch and have some fun."

She kissed me again, quickly, as a parting gesture, and got out of the car. I was not sure how to process everything that was just said, but I know I needed to get out of the car and go about our planned day.

I was surprised at where Shana had brought us. It was a local non-franchise smoothy place. When I asked her about it, she replied, "You told me liquids only today right? Given who your appointment is with this evening, I am thinking you are on the same diet too?"

I frowned and agreed with her. Lunch went by quickly and was surprisingly refreshing. However, my mind was still on what was said and ultimately trying to decide what I wanted to do. Our conversation floated across a number of other things, while only slightly touching on this evening's plans or what she had said to me.

Before I knew it, we were back in my apartment. Shana looked at the clock and commented, "I need to be out of here by 6:30 and you probably need to leave about the same time, right?"

I quickly looked at my calendar. My appointment was at 7 pm and I needed to be downstairs by 6:40. I looked back at Shana and replied, "That is correct. So that gives us about two hours and forty minutes then. We need to get started."

"What do I do?"

"We are going to get very personal during this process. You might get embarrassed."

She laughed. "Megan, I am so comfortable with you. I feel like I can do anything with you. Plus, I really want to do this tonight, so I am going to power through no matter what."

"Okay. Well, there are going to be three parts to this process. Part one, is maybe the most important. It is about cleaning your anal cavity out. You would not want to have any bad stuff come out while you are doing the deed."

"Oh heavens no. Okay, what is part two?"

"Part two is me preparing your sexy backdoor for penetration."

Shana giggled. "How do we do that?"

I giggled back at her, "By me penetrating you of course. I need to loosen your sexy asshole and get it ready for some dick."

Shana appreciated my crassness. She laughed and asked, "And part three?"

"Part three is about you getting me ready for my date tonight. So, everything I am going to do to you, you have to do to me. Got it?"

Shana laughed and clapped her hands together. "This is going to be so much fun!"

"Let's see if you still feel that way after we are done. Let's go. Follow me."

I led Shana to my bedroom and told her to get undressed. I went to the bathroom and turned the shower on and got the supplies ready. When I came out of the bathroom, Shana was lying on the bed, with her legs spread wide, masturbating.

As much as that sight turned me on, I had to keep us on schedule. "Shana, what are you doing?"

"What does it look like I am doing? I am taking the edge off. Do you want to help?"

"I completely want to help, but I'd like to get the process started please. Come on. Follow me."

Shana reluctantly pulled her fingers away from her sweet little slit and rolled off the bed. She came into the bathroom soon after I did. I instructed her to follow me into the shower.

Once we were in the shower, I walked her through how to use an enema, and told her we were going to do several of them. We spent almost an hour cleaning ourselves out, preparing for the evenings planned activities. To my surprise, Shana took it seriously and did not try any hanky panky.

We then headed to the bedroom where I instructed Shana to lie on the bed, on her back. I went over to the nightstand on the other side of the bed and pulled out a number of toys and plugs of varying sizes and a bottle of lube.

Shana teased me a little as I dropped the toys on the bottom of the bed. "I guess those are for part two huh?"

I smiled at her and said, "Yes, of course."

I knelt between her legs and moved over the top of her. I interrupted her mischievous look with a passionate kiss. I was a bit of the aggressor, driving the pace, which meant I did not linger too long before I started to move down her neck, leaving a trail of kisses and love.

Shana gasped as I took one of her nipples into my mouth. I sucked hard quickly bringing it to attention before I moved over to the other one. I felt we were a little behind schedule, so I moved quickly.

Within a couple minutes I had my mouth on her pussy. My goal was different than usual, where I work to bring her to an orgasm. This time, my focus was on getting her worked up and horny without giving her a release.

I ran my tongue around her pussy, sucking in her slightly protruding lips. Shana purred at the attention. I used my fingers to gently spread her lips, so I could lick up her seam and tickle her clit. Swiftly, I moved back to her hole before she got too into it. I heard a slight sigh in her moan.

Using my tongue, I penetrated her warm box, circling around the entrance, teasing her before pulling away. As I sensed her frustration, I slid a finger into her wet opening and curled it up slightly, hitting her g-spot. I massaged it gently, causing her to groan. I tried to refocus on the intention of this exercise.

I added a second finger and pulled away from her sensitive button. I kept working the two fingers in and out, going deeper and deeper until I got to the end. I tilted her legs back further with my free hand, exposing her pink star. I took a brief look at it, as it would never look the same again after tonight.

My fingers kept jabbing her pussy, distracting her slightly as I used my tongue to moisten her back entrance. After leaving a generous amount of saliva, I pushed my tongue in as far as I could to her dark passage. I heard her gasp, and pull her legs back farther, inviting me in.

"Yeessss Megan. I love that. Keep doing that." She pleaded.

I obliged her for a couple more minutes, but knew I needed to keep moving forward. I finally removed my fingers from her dripping pussy and slid my glistening middle finger into her anus, being gentle and careful to start.

Her moans told me I could keep going. I pushed my finger all the way in and moved it around in a circular motion. She kept giving me positive responses, so continued to press the issue. I put my tongue on her pussy, drinking up the copious amounts of juices she was excreting.

"Oh my god Megan. That is so good. Don't stop. Please don't stop."

I kept my mouth exploring her pussy while I deftly inserted a second finger into her backdoor. It took a few minutes, but I finally had two fingers deeply pistoning in and out of her tight asshole. Even though I was actually trying to avoid it, Shana achieved an orgasm anyway. As I sucked it in and swallowed her sweet juices, I recognized that I should have known that she would like anal, and this would be pleasurable for her.

Following her orgasm, I pulled my fingers lose from her clinching orifice and grabbed the plug off the table. It was a small, daily wearer type, with a metal dollop and a heart shaped knob. I felt like her tight hole was ready for it without much additional lube. So, I stuck it in my mouth, lathering it up with saliva and then aimed it at her backdoor entry.

I watched her face as I slowly pushed it in. Her expression showed pleasure as opposed to discomfort. That made me want to move a little faster. I continued to watch her face as I moved the plug in and out of her ass, picking up the pace every minute or so. I started rubbing her pussy to offset any discomfort she might have had.

Shana started yelping, "Oh Yeah, Megan. Fuck my ass. Faster. Faster... Oh, I am gunna cum!"

I could not believe how well she had taken to anal. I increased my movements to a blistering pace until she finally groaned through an orgasm. Once again, my mouth went to her pussy to clean up her delicious juices.

She groaned again as I pulled the plug from her now slightly elastic hole. Just as she started to complain, I reached for the middle size dildo. Since she was adapting so well to the process, it was time to up the ante.

This dildo was completely smooth, but thicker than the plug. It was obviously longer, as I was now going to test how well she took to deeper penetration. This time I put some lube on the phallus before attempting to push it inside my lovers recently virgin asshole.

I looked at Shana again before I broke open the seal again. She had a strong look of anticipation. Her mouth opened in slow motion as I started penetrating her dark passage. I went slowly and only gained depth as I felt she was ready. I was having flashbacks of several months ago when Nicole went through this same process with me. I tried to put myself in Shana's position right now and account for all the feelings I had.

Though, it seemed as if Shana was taking to it slightly faster than I did. Don't get me wrong, I had one helluva orgasm the first time Nicole put me through the anal ringer. But as I looked at Shana, she seems to desire what I am doing and the look in her eyes is one of lust and hunger.

I started rubbing her clit with my left hand as I began to push the dildo into her deeper. Shana closed her eyes and started to expel long, drawn-out moans. In and out I went, slowly and deliberately. I glanced at the phallus. I was halfway in, and the remaining portion was still glistening with lube, so I was good to move forward.

I asked, "Are you ready Shana?"

Her reply was emphatic, "Yes. Give it to me!"

I turned my concentration back to the phallus. I began to push it in deeper with every thrust, maybe a quarter inch with every pass. Within a minute, this medium size dildo was completely submerged into my friend's tight ass.

She groaned, "Oh my god that is good. Fuck me with it, Megan. Give it to me."

I gave into her wish and started moving the dildo in and out with intention. I knew what she was after, and I seemed to be powerless to not give it to her. The least I could do is accomplish what I wanted to, in loosening up her hole and getting it ready for real anal sex later tonight.

The look on her face was pure pleasure, with the smallest hint of surprise every now and then. I looked back at my motions and smiled. I was fucking her tight little hole with a solid, seven-inch fake cock. This was as big, if not bigger than most men. She was taking it like a champ and was on the verge of another orgasm.

I put my mouth on her pussy again, flicking her clit a half dozen times before I heard her yell out. Her mid-section shook and jerked as I slowed down my actions. I tasted her sweet juices flood my mouth once more.

As her orgasm finally subsided, I looked her over, and saw that she was breathing heavily, and still slightly shaking. I commented, "Shana, are you okay?"

She took several deep breathes and replied, "Is anal sex always this good?"

I laughed. "Not necessarily. I am glad you seem to like it though. It will make tonight so much better."

Still breathing heavily, Shana replied, "I really wish I would have done this earlier. I actually do like it. Like, a lot!"

"I could tell. We have an issue though."

She lifted her head and opened her eyes. "What is the issue? There is not poop on the dildo is there? Oh my god, tell me there is not a mess!"

"No Shana! Our issue is that I was going to do the next size up to make sure your little booty hole is completely ready. However, I think if I do that, and you have another orgasm, you are done for the night. You will not have anything left for your date."

There was a little bit of a silence as Shana considered what I said. Finally, she responded. "Why don't you go through the work to get it all the way in, but don't fuck me with it."