Next he showed me a picture of Sonny's under boss Christopher and his girlfriend Adriana. She was about my age and the plan was to befriend her. She would introduce me to Christopher who would introduce me to Sonny.

Lastly he gave me an emergency phone number to put in my purse. It was written in code with a phrase 'Its warm outside today'. He told me only to use it if my life was in danger. I said goodbye and told him I would see him when the mission was over.

With the pictures was Adriana's address and license plate number. I figured the easiest way was to tail her when she left home and wait for her to stop somewhere I could make contact.

She was a stylish girl so I knew I had to make my look similar to hers. I had a ton of cute casual dresses that would work for a meet up. I decided on a red one that reached my knees and showed off my cleavage.

Emily had hammered it into my brain about matching, so I put on a red bra and thong. I made my hair look big and put in large hoop earrings. Of all the new things I had been wearing, the only thing that was still uncomfortable was my earrings. Sam had assured me that I would get used to them. I did my makeup and slipped into white open toed shoes that showed off my cute toenails.

Adriana had a nightclub that she ran so I knew she wasn't an early riser. I got to her house at 9am anyway, parked down the block and waited. I was getting ready to give up when she walked out just before noon. Her picture didn't do her justice, she was a very beautiful woman.

I followed my training and kept my distance as I followed her. I doubted she would even realize there was someone behind her, but better safe than sorry. Her day was pretty boring and there weren't any chances to approach her at first. She drove to a house which I assumed was her mother's. Then she went to the bank and the post office. It was 3pm and I had a long day already with nothing accomplished. Then finally she drove to the mall. Perfect!

I parked my car in a different row from her, but didn't let her leave my sight. I followed her into the mall and into a cute little clothing store. This was going to be easier than I expected. I kept my distance at first, but when she picked up a black and white dress, I pounced.

"That would look amazing on you," I said.

"Are you talking to me?" she asked.

"Oh I'm sorry, there I go with my big mouth inserting myself into other people's business. I was just saying that dress would look totally hot on you!" I said.

She held it up against her body and looked in the mirror.

"You think?" she asked.

"Most definitely, it will show off your cleavage and make your ass look spectacular. Assuming that's what you're going for," I said.

"Speaking of cleavage, look at you. I love that dress," she said.

"Gee thanks, but it's not as pretty as yours," I said.

"Where did you get it?" she asked.

"I work for a personal shopping service," I said, "I have access to tons of things."

"That's so cool," she said.

Then she looked at the price tag of the dress.

"Forget that," she said.

"How much is it?" I asked.

"Too much. My boyfriend would freak if I spent that much on a dress. He likes to brag about how much money he makes, but when it comes to my shopping he gets upset," she said.

"That's too bad, because that dress was made for you. If you want I can see if I can get it for a discount. Sometimes I get up to 50%," I said.

"Wow, really? That would be great. I'm glad I ran into you," she said.

I stuck out my hand and said, "Donna."

She shook it and said, "Adriana."

"I was going to sit with a Starbucks," I said.

"So was I," she said.

"Wanna go together?" I asked.

"Definitely," she said.

We walked over and got some coffee. We told each other a little bit about ourselves. I made up a story about being new to the area and not having a lot of friends. She told me what I already knew about her owning a club with her boyfriend. We became fast friends and agreed to meet for lunch tomorrow.

We both left and I waited for her to drive away while I sat in my car. I let fifteen minutes go by just to be safe before walking back into the mall. I went into the store and bought the dress in her size using my new debit card. I would surprise her in a couple of days and tell her I got it with my discount.

The next day I had insisted on picking her up for lunch. I got there early on purpose which worked perfectly when she let me in. She told me to make myself comfortable while she finished getting ready.

I looked around her house to see where I could put one of the pens. Just past the kitchen, I spotted an office with a desk covered in papers. I took a pen out of my purse and put it in the cup that had at least 10 other pens. I walked back into the kitchen when Adriana came in.

"I know we're going out to eat, but do you have a bottle of water? I'm so dehydrated today for some reason," I said.

"Sure," she said, pulling two bottles of water out of the fridge.

We had a nice lunch and we talked more about our lives. She told me more about her boyfriend and I told her I had a couple bad breakups, but hadn't really tried to meet anyone yet in this town. I baited the hook and told her that I wasn't a fan of dating apps and preferred being set up by a friend.

Step One of my plan was going well. I became close with Adriana and we were hanging out all the time. She brought me to her club a couple of times and I was able to plant a pen in the private office. She had mentioned that her boyfriend sometimes met some friends there.

A month had gone by and she still hadn't introduced me to her boyfriend. I casually brought him up in conversation, but she would tell me he was working. I had swapped the pens twice and hoped there was some good info on them. When they told me the timeframe for the mission was a year, I thought they were crazy. I expected to wrap this up in a month or two and go back to my normal life.

Two more weeks had passed when Christopher finally showed up at the club. Sonny was with him and they went right to the back office. Adriana tried to introduce me to him, but he blew right by us. She mumbled that he could be such an asshole sometimes. Hopefully, I would be getting some good audio recordings though.

After another month things finally got interesting. I had formally met Christopher and he would hangout with me and Adriana regularly. He tried to introduce me to some of his friends, but I would always say I wasn't interested. Then one night Chris and Sonny came into the club and sat at a table.

"Who's that?" I asked Adriana.

"With Chris? That's Sonny. He's the Boss...I mean Chris's boss. It's hard to explain," she said.

"He's kinda cute," I said.

"You think? He's like ten years older than us," she said.

"That's not always bad. Older guys know what they're doing," I said.

"Want me to introduce you?" she asked.

"Sure, maybe it's time for me to get back in the dating scene," I said.

I had always dressed sexy when I went to the club just in case. Tonight I was coincidentally wearing my hottest black dress. It was so low cut that my boobs were threatening to pop out. It was tight to my body and clung to my ass which it barely covered. I had fake long eyelashes in with big earrings. I had treated myself to a pair of black Louboutin heels that made my legs look amazing.

"Hello ladies," Sonny said as we approached the table.

"This is my friend Donna," Adriana said.

Sonny kissed my hand and said, "Wow, where have you been hiding her?"

"I'm new to town, but I've been around. We just wanted to say hi. We didn't want to interrupt," I said and started to back away.

Part of my agent training was a lesson in sales. One of the most important things I learned was to offer something and then take it away. I wanted to see if he would take the hint.

Sonny gently grabbed my wrist and said, "No, please stay."

Bingo! I thought to myself.

We talked and I slowly started to rub Sonny's arm. He upped the ante and began to rub my leg. It felt nice to be touched again. These last couple of months I had been dressing so sexy and hadn't had any type of release. When Sonny asked me if I wanted to go somewhere private I agreed.

He took me to the office and we sat on the couch. His tongue was in my mouth in an instant and we were making out. He was rubbing me all over my body and my left breast popped out of my dress and bra cup. He started to stroke my nipple and I got the tingles.

I was moaning in his mouth and my groin was starting to throb. I hadn't felt that sensation down there since the last day of my training. I wasn't sure how far I was willing to take this on the first night though. Then we were startled by a banging on the door.

"Sonny, we need you!" Someone screamed.

He broke the kiss and said, "Dammit! Stay right there. I'll be right back."

I made up my mind that I had enough for tonight. I couldn't let myself have a one night stand. I needed to get into a relationship with him so I could get as much incriminating information as I could.

I stood up and put my boob back in my dress. I checked my face in the mirror in my purse and fixed my smudged lipstick. I grabbed the pen off the desk and replaced it with a new one. I started to walk to the door and Sonny came back in.

"Leaving already?" he asked.

"Yeah, sorry, I have an early morning. I had a wonderful time though," I said.

"No, I'm sorry, fucking assholes are always interrupting," he said.

"No worries. You can make it up to me by taking me to dinner tomorrow night," I said.

"Done! I'll get your details from Adriana," he said.

I gave him a big kiss on the lips and said goodnight.

When I got home I was all worked up. I knew I was doing a job and playing a character, but I was starting to enjoy being Donna. It felt great to dress up all sexy and be desired. Plus I'd have to admit that I really enjoyed being kissed and touched.

I got undressed and decided I would try to relieve some of my built-up energy and pleasure myself. I got on my bed and started to rub my nipples. The goosebumps came back, but it wasn't getting me there. I tried to finger myself, but I remembered I couldn't reach deep enough. My mind flashed to the bottom drawer again, but I still wasn't ready to use those things, so I just went to sleep.

Sonny and I started dating and like a good girl, I made him wait until the third date to give him a blowjob. The first two dates were full of kissing and playing with my tits, but neither of us had cum. It's a little strange for me to say, but I really liked him. I had read his file and knew he was a dangerous mobster, but with me, he was nothing but sweet.

After dinner on our third date, he finally took me to his house. I had left word through one of the recordings to leave me extra devices. Brian had gotten the message because there were double the amount of pens in the locker. Once inside Sonny's house, I asked him for a tour. I strategically placed six pens all over his house and making a mental note of where they were so I could get them back.

Once the tour was done we were back in the living room. He had opened a bottle of wine and his tongue was in my mouth again. I reached behind me to loosen my pink dress and let it slip below my boobs. I unclasped my bra and let them breathe. I broke our kiss and pushed his head down. He had played with my nipples with his hands enough, now I wanted to feel his mouth on them. He took the hint and started to suck on my left tit.

I threw my head back and moaned in pleasure. Then I reached down and felt for his crotch. He was hard for me and I rubbed his dick while he devoured my breasts.

He lifted his head up for a second and said, "Damn you're hot!"

"Mmmmm," I moaned as he continued his oral assault.

"I am so hard for you right now," he said.

"I can feel it," I moaned again.

"I know you wanted to go slow, but how would you feel about helping me out," he said.

"I thought you'd never ask," I said.

I unbuttoned his pants and lowered his zipper. He lifted his ass off the couch slightly and I pulled his pants and boxers down. His huge dick sprung out and was standing straight up. It was the biggest I had ever seen. I dropped to my knees and got ready to give my second blowjob.

I was a little intimidated by the size of his cock, especially the head. I opened my mouth as wide as I could and closed my lips on the tip of his dick. My cheeks popped out as I started to take him inside me.

"Oh yeah. So Good!" he cried.

I took him as deep as I could and then started to bob my head. He was breathing deeply and then I started to give him a tongue bath as I sucked him. For only my second time, I was doing a great job based on the sounds he was making.

His dick stiffened even harder and he yelled out that he was going to cum. I didn't slow down and he blasted my tonsils with his load. I knew getting him off was a means to an end, but I wished there was a way to relieve my sexual frustration too.

"Wow Donna, that was amazing!" he said.

"You're welcome," I said.

I got off my knees and pulled my dress back up, forgoing my bra. I sat back down next to him.

"Would you like to join me in my bedroom?" he asked.

I knew what he wanted to do in there, and I wasn't sure I was ready. I had only put a finger in my vagina and wasn't sure what would happen with something much larger. My thoughts were broken when his phone rang.

"Who is this now," he said, answering the phone, "Yes?!"

I couldn't make out the words on the other end of the call, but they were talking very fast.

"Alright, fine," Sonny said into the phone.

He hung up and looked at me with a pissed-off face.

"I'm sorry sweetie, that was work and I have to go," he said.

"Awww," I said, not really disappointed.

"Do you mind taking an Uber home?" he asked.

"Not at all," I said.

"And tomorrow night we're gonna pick up where we left off. I'm shutting the phone off and telling everyone that unless someone is dead, I'm not to be disturbed," he said.

"Sounds wonderful," I said.

He leaned in to kiss me goodnight. I wasn't sure if he remembered that he just came in my mouth, but he didn't seem to mind.

When I got home I had no choice but to open my bottom drawer. Sonny was going to fuck me and I needed to be ready. Emily had bought me three different sized dildos, but none were as big as Sonny. I started with the smallest one just to see how it would feel. I remembered her saying that it wasn't really going inside me, and it turns out it didn't feel like anything.

The second one didn't feel like anything either, and then finally the third one was big enough to reach my trapped dick. Not by much though. I thrusted it in and out of my fake vagina and while there was a light sensation in my groin, it was not enough to get me off. I had no idea if Sonny's dick would have the same effect, but I would likely need to pretend that it did.

The next night Sonny took me to dinner and wasted no time in taking me to his bedroom. I had worn a white dress with sexy white lingerie underneath. He didn't know it, but Donna was about to lose her virginity. The only part of my outfit that wasn't white was my black stockings which gave a great contrast to my look. Sonny unzipped my dress and revealed his prize.

"Wow Babe, is that for me?" he asked.

"I wanted to look extra special for you," I said.

"That lingerie is so hot," he said, "Can you keep the stockings on?"

"Whatever my man wants," I said.

I reached back and unclasped my bra. His mouth was on my left nipple and he pushed me back onto the bed. He moved up and kissed me as he lowered his pants. He kicked his shoes off and I helped him take off his pants and boxers. He kissed my neck and then began to pepper my body with kisses as he worked his way down.

When he reached my belly button I lifted my hips a bit to give him a sign. He grabbed the waist of my thong and pulled it down to my ankles. I lifted my right leg and made a kicking motion which tossed my panties onto the floor. Then he kissed my pussy, but I didn't react. Realizing what was happening I gave a fake sigh of pleasure. It would be hard to keep up the fake act of getting eaten out and fucked though.

"Mmmm, baby that's so good, but I've been thinking about you being inside me all day," I said, saying something I never thought I'd say.

"If that's what you want," he said, "I was going to pay you back for last night first."

"You can pay me back by fucking my brains out!" I said.

Seriously, where were these words coming from, I thought.

Sonny got on top of me and I spread my legs. He reached down to line himself up and I made sure to look down so I could see when he entered my vagina. He grunted and slid inside. Just like the dildos I didn't feel anything.

When I figured he was deep enough I groaned, "Ohhhh so big!"

"You like that, huh?" he asked.

"Oh yeah," I agreed, and we were off.

He continued to push and I finally felt his skin touch mine as our groins met. He held still deep inside my opening and I could barely feel him touching my dick.

"Are you okay," he asked.

"Better than okay," I lied. "Please fuck me."

"Your wish is my command," he said.

I went into full acting mode and started to moan and groan. The rhythm of his thrusts, the feeling of our bodies touching was nice, but there was no way he was going to make me cum. I pretended like I was going to and tried to time it with his climax. When he came I felt the warmth fill my cavity. At least I finally felt something.

"That was wonderful, Babe," I lied.

"Well worth the wait," he said.

"I'm gonna get some water, would you like some?" he asked.

"Yes please," I said.

He really was so sweet. How could this wonderful man be this violent sociopath everyone said he was?

He came back and asked, "Would you like to stay the night?"

"I would love to, but I have an early morning again," I said.

"Why don't you just quit that job and move in with me?" he asked.

He caught me off guard and I said, "What happened to going slow?"

"It's just that I can see myself falling for you and I'm used to getting what I want. I didn't mean to pressure you," he said.

"I can see myself falling for you too," I said, not sure if I was lying this time.

"So why waste time?" he asked.

"Give me some time to think," I said.

"Okay. Let's get dressed and I'll take you home," he said.

After he dropped me off I got undressed and took a shower. Emily had showed me how to clean myself out, but I'll spare you the details. I put on a nightie and poured myself a glass of wine. I sat on my couch and thought about my options.

On one hand, living with Sonny would make it much easier to plant the bugs and retrieve them. On the other, did I want to get that close? When I said I thought I might be falling for him it scared me. Number one, this is a mission and number two, I don't like guys. At least I don't think I do. I decided I would keep our relationship as is and would reassess in the future.

Sonny and I continued to date. I would blow him and he would fuck me, however, I still wasn't able to cum. I was really aching to have an orgasm and did something drastic.

One night after some unfulfilling sex I opened my special drawer again. I remembered what Emily had said about anal penetration, so I took out some lube and eased the butt plug into my ass. It felt strange, but I decided to sleep with it inside me. When I woke up I had almost forgotten I had it in. It didn't seem that bad and I kept it in all day.

That night Sonny took me out and when we were back at his place I made him an offer that every man likes to hear.

"Babe, have you ever thought about anal?" I asked.

"Are you asking me what I think?" he asked back.

I bent over and pulled my green dress over my ass. I lowered my green thong and wiggled my ass at him, showing him the butt plug.