The Robertson's Sissy Ch. 17

I slid my hand down her back and caressed her bare ass as she cooed in approval. I worked my fingers down until I felt the soft wet flesh of her recently satisfied pussy. Gently, I rubbed it as she squeezed my shorts and tried not to moan loud. I felt her hole moisten as I slipped a finger inside her. Her pussy was still so hot and velvety but she quickly pulled me out and turned to stare at me.

Slowly she raised my hand to her mouth and began sucking my finger.

"Mmm I can still taste your cum," she giggled before seductively sucking again.

I thought this was going to be a short tease but Lela kept blowing my finger and moaning on it. My cock stiffened in my panties as I watched her nipples slowly harden and poke through her shirts.

"Baby, You make me so wet," Lela whispered before deepthroating my finger.

"I think your nipples are showing me how horny you are," I joked.

Lela looked down and pulled my finger from her mouth as she giggled,

Her hand slid to her chest as she squeezed her breasts together and played with them.

"You have no idea how much my titties missed you," she told me before opening her mouth in an inviting way.

I pushed my finger back into her warm mouth as she moaned while sucking them. Aggressively she kneaded her firm breasts while sucking me like a little whore. Right when I really started enjoying it she stop playing with her breasts and sucking on my finger, but she wasn't done. As I leaned back against the tree she sat up and straddled my lap as her short skirt struggled to cover her firm round ass. Lela stared at me, inches from my face as she sucked my finger once more before slowly running it down her chest and between her cleavage.

"I missed you fucking these titties. I missed feeling your big hairless balls sliding across my stomach as you fuck my soft flesh. Ugh, the ending is always the best. When I would look down to see your swollen cock head breach my titties and spit a fat load in my face. The thought of your warm cum splashing and dripping down my chin and neck drives me crazy."

Lela wasn't the only one being driven crazy as her dirty talk and soft breast fucking my fnger had me rock hard. My cock swelled as it poked her pussy causing her to smile, she knew I was ready for what she wanted next. Lela allowed my finger to slip from her breasts as she kissed me while running her hands between my legs. Softly, she stroked me through my shorts and panties before sliding off and laying down with her head in my lap.

I sat mesmerized as she popped her ass up while looking around to make sure we were alone. She pulled my panties to the side, freeing my ready cock though she didn't immediately take me into her mouth. Instead she stared while licking my entire length, flicking her tongue as she teased my tip. My cock would twitch when she reached my most sensitive parts causing her to giggle at my teasing.

As she licked she talked to me "Baby, do you love me?"

"Of course I do Lela."

"Like love me enough to do anything for me? If you knew something turned me on so much would you hesitate to do it?"

At this point I would have robbed a bank if she requested. "Anything Lela. What do you want me to do?"

"I don't know. But we will test out your love and willingness tomorrow night," she said with a slutty smile before finally taking my cock into her mouth.

I missed her talented little mouth dearly and didn't even care what she might do to me the next night. After her absence this week my obsession with her was clear and I would put myself through anything to keep being her sissy. She sucked me slowly as her plump glossy lips massaged my cockhead. Each time she pulled off my cock and loud 'pop' escaped from the extra suction she blew me with.

Suddenly she stopped and slid my cock back under my shorts. I opened my eyes to see a pair of joggers coming down the nearby trail. Lela laid there smiling up at me, laughing at us nearly being caught. Her beauty made my heart melt and I wanted to pin her down and have my way with her but I knew Lela ran this show and to not take control from her.

We watched as the couple finally disappeared down the trail before Lela freed my cock a second time. This time she cupped my balls while slowly sucking me deeper. We sat like this for sometime as I rubbed her back and ass before she was ready for the next step. Slowly she positioned herself between my legs, allowing me to have a perfect view of the braless breasts as she laid back down on her stomach.

Lela leaned in and began giving my needy balls the royal treatment. Slow, long licks from the bottom of my scrotum to my shaft. Occasionally kissing and allowing each ball to be taken into her mouth.

"I missed these big balls and the heavy load they spit. Have you been working on the exercises we learned?" She asked as she tickled my balls with her tongue.

"Yes, I haven't been able to stop my ejaculation yet but my cock seems so much harder and I cum a lot more."

"Well I can see you are a lot harder," she giggled while holding my extra swollen cock to her face.

The teasing had to stop and fortunately she was ready as well. Slowly, she took my cock back into her warm mouth and slid down my length. I sat amazed as I always was when she deepthroated my entire length. She picked up the pace a bit as her tight little throat squeezed my cock each time she pushed down. Slowly she slid back up and allowed my cock to escape momentarily.

"Well be a gentleman and hold my hair," she ordered with a small laugh.

I grabbed her hair in a ponytail as she slowly worked my length. With her hair up I was able to see the entirety of her beautiful face and eyes. Her teasing had me raging and I knew I wouldn't last long like this.

"Do you want me to try and hold back my cum?"

"Fuck no."

"I want to cum down that tight little throat of yours," I told her as lust took over me.

Lela just wiggled her ass as she shook her head no, "I haven't tasted you all week. I can't taste you in my throat. You are not making me wait any longer."

With that she plunged back down the length of my cock until her nose made contact with my pubic area. Her throat massaged me but this time she added a little extra. Her wet tongue escaped her mouth and slowly licked my balls. I was completely taken back, fighting the urge to cum just from the site and thought of what she was doing.

Lela would come up for air each time before slowly sliding back down. Each time she bottomed out her tongue would tickle and massage my balls again. Her oral skills were top notch and it wasn't long before her talented mouth brought me to orgasm. I held her hair and grunted as my body seized with clenched muscles. Right on cue Lela slid up my length and sucked just my cockhead as the first spasm of cum blasted her mouth.

She softly stroked me and grunted with each powerful pulse that splashed cum against her tongue. Her lips tightened around my cock to make sure not a single drop escaped her eager little mouth. I felt flushed with warm sensations as my orgasm subsided but Lela wasn't done just yet. With a mouth full of warm cum she continued to suck my sensitive cock. I struggled to fight from pushing her off and finally she allowed my cock to be free as she giggled before laying her head down and swallowing.

"Oh my god babe. You cum like a fucking rocket now. You still taste so sweet though," she said as she caught her breath.

She laid there and kissed my thighs as my cock slowly softened. Just as I was about to pull my shorts up Lela stopped me and straddled my lap again.

"Now since you say you are willing to do anything I want, I know one way to prove it," she whispered as she kissed me.

Lela reached into her bag and removed something small before bringing both hands to my limp cock. I looked down to see her starting to attach the cock cage she made me wear and quickly protested.

"Lela please, I hate that fucking thing. Please no."

"I thought you would do anything. You should know by now that I will make it worth it. I know women who make men wear it for days or weeks. At least I let you cum often when you wear it. Plus you've been a little whore around town this week so I need to make sure you're not being naughty unless you're with me."

I sat silent as she finally secured it before putting the key around her neck with a huge smile.

"Have fun with Jenny tonight," she laughed as she pulled my shorts up and rested her head on my lap again. I forgot about Jenny and how I was now fucked for tonight.

"No. Wait. Please take this off babe. I can't see her with this. What am I going to do?"

Lela just laid looking up at me with her long soft hair flowing across my lap. Her face glowed with the biggest smile as she knew she had me. She loved teasing and humiliating me so I knew she wasn't going to take it off.

"I don't know. Be happy I am letting go there but even though you are, your cum belongs to me. If it makes you feel better the other reason I knew you were seeing her is because she was blowing up my phone all week. She was trying to take your spot behind your back. Think about that when you deprive her of your hard cock later."

I was taken back by this, "She called you up all week? Did you see her?"

"Nope. I wasn't lying when I said I was all fucked up this week. That should show you how much I missed you because she is fucking gorgeous and her tight little twat would have been quite comforting. When she blew up my phone I knew you talked to her and she found out about what happened, which meant you two were fucking. I didn't care, well, I do care but I knew you would be back when I called."

"I am back Lela. You know I want to be with you. Can you please let me have one last night? This is honestly going to be a horrible night, more for me than her."

"Oh but it's going to be an amazing night for me! I'm going to lay in bed with a glass of wine. With a pussy and belly full of your cum thinking about the two of you struggling. The only down side will be thinking of how you just begged me to have a good night with her after saying you were mine. Now I'm a little confused and might need to make you prove yourself tomorrow night."

"Stop Lela. You win. I love you and you don't have to make me prove anything. I'm willing to do anything and won't complain anymore," I gave in but she could tell I wasn't happy.

"I don't have much longer. Come lay down with me for a bit," she begged, trying to be all cute with me.

I pushed her buttons enough and decided not to push anymore. Nothing good ever came from me resisting her and I should just be happy I was back under her control. I laid down with her as we kissed for the last 20 minutes of our time.

Unfortunately we couldn't stay like that all day and we got ready to leave. We folded the blanket up and headed back to the car. She held my hand and walked as excited as I've seen her in some time. We packed up the car before pulling out of the lot onto the main road.

"I have something for you to look forward to other than our vacation," she told me as she grabbed my hand.

"Hopefully not another cock cage," I said sarcastically.

"Close. All week I went shopping and bought a whole bunch of new toys for us and a bunch of sexy things for you to wear."

She was very happy to tell me about this so I knew she bought some really kinky toys and lingerie. I couldn't wait to wear whatever she bought and the thought of lingerie caused my cock to twitch in the cage. We pulled into the parking lot and parked next to my car. I was still upset about my ruined night ahead and grabbed the handle to leave.

Lela wasn't having it and grabbed my hand, pulling me back. She embraced me in a deep kiss and I couldn't resist kissing her back. Her hands slid up my thigh and squeezed the cock cage before she suddenly stopped.

"Oops! I forgot!" She laughed as she teased me.

I stepped out pissed off and walked to my car. Lela watched me with her window rolled down while biting her lip. I got to my car and turned to her questioning the look she was giving me.

"What Lela?"

"Nothing. Was just checking out that sweet little ass of yours. I can't wait to get rough with it."

I just turned and put the key in to unlock my car.

"Matt come here," she said softly.

I wasn't happy but knew not to ignore her. I turned and walked to her window before she pulled my face in.

She gave me a soft kiss before saying, "I love you and missed you. I'm not gonna let you leave mad. Relax. Tomorrow everything will be straightened out. Ok?"

I just shook my head before giving her one last kiss. We parted ways for the day and I drove home trying to figure out what I was going to do now with Jenny. She wanted to see Michelle tonight which was good but I knew she would at least want my cock at some point. Jenny turned into quite the cum slut so she may need to fuck it out of me. All I knew was that my cock was out of commission tonight and that she wasn't going to be happy.

I made my way home and spent my afternoon being lazy around the house. I thought about tomorrow night at the Robertson's and grew scared of Chuck. He hated me and being around him was going to be rough. Lela did tell me that only she is able to punish me and the only one who calls the shots with me. As long as she was with me I knew she would look after me until he lightened up.

Lela on the other hand said a few concerning things today though. She asked me if I would do anything she asked and also how she might need to test my love with her. I had an uneasy feeling about it but I would do anything to be with her. After all she put me through I've gotten used to her rough and humiliating ideas so I was confident I could take and enjoy all she threw at me.

As evening approached I retreated to my bedroom to pick out how Michelle would look that night. I dug through the bag and found some unworn lingerie, a dress, a skirt, a blouse and my bikini left. I decided to just take the whole bag with me and wear whatever I felt like in the moment. I grabbed a change of clothes and hit the shower to clean up from my long day with Lela.

As I washed I couldn't stop staring at the dumb cock cage Lela made me wear. I tried to wiggle it loose but it wasn't coming off. It was snug around the base of my balls and a long curved plastic piece covered my flaccid shaft and cock head. The hardest part would be trying to stay soft as any erection became painful. I decided Michelle would have to double down with her tongue and ass tonight and washed the rest of my smooth body clean. I closed my eyes under the warm water as my hands slid up and down my body, feeling the curves my body started to acquire.

My shower ended with me fighting off an erection caused by my own smooth feminine body. The cock cage was quick at shooting down any erection I started to got. I dried up and threw on a pair of shorts and t-shirt. Jenny dressed up last night and I thought about doing the same in return but I had no motivation to do so. She wanted Michelle tonight so as long as she looked good I knew Jenny would be happy.

As I killed time I laid in bed and thought of Jenny. I felt bad her husband neglected her sexually and I wish I could satisfy both her and Lela. Jenny was turning out to be quite the kinky and dominant woman like Lela was though I knew it was mostly a show. I also wouldn't be able to see her when her husband was around so it was better that I was smitten by Lela. Tonight I would give Jenny a night to remember though.

I decided to shoot Jenny a text, "Hey, what time should I come by?"

Lela already knew I was seeing her so it didn't matter if she saw my message.

Jenny quickly replied, "Just finishing up eating out with some lady friends. Is an hour ok?"

"Yes, see you in a bit."

Jenny finished off the conversation with three emoji faces that would come to signify the night. A kissy face, a winky face and finally the smiling devil. She said she wanted to have her way with Michelle tonight and she was going to do just as planned. I decided to quickly eat something since Jenny was already eating out. In the kitchen I made a sandwich and chatted a bit with my mother. I told her I was going to the Roberton's that night as the following night I would be at a party late. I also told her that the Robertson's invited me on a vacation though they were still planning out where.

I had all my basis covered but didn't need to try hard with her. My mother always believed what I told her and never had a reason to second guess me. She thought it was great that I was going to go away for a while and it reminded me about my passport. I finished eating and retreated to my room and dug through my drawer until I finally pulled it out. It was still good so I put in on my dresser until needed.

I carefully packed my wig into my bag and got ready to leave for the night. I told my mother I'd be home sometime tomorrow and walked out to my car. It was now dark out and the summer night was warmer than normal. I drove to Jenny's house and thought about how to explain the cock cage and how to work around it. There was no good way to do it but hopefully she recognized I had no choice.

My heart raced as I pulled up her street and raced even more when I saw her in the driveway getting out from her car. She must have just arrived home and she smiled as I pulled in. She looked fucking banging with short shorts and button down blouse. Her hair was up in a bun leaving a perfect view of her gorgeous face.

I stepped out of the car and greeted her but knew to quickly get inside the house as to not be seen by anyone. I quickly followed her inside and dropped my bag on the floor as she shut the door and immediately kissed me.

"Gosh. I thought about you all day. Come to the kitchen," she said as she kicked off her sandals.

As she walked she began unbuttoning her blouse past her large breasts revealing the maroon satin bra. She left the last two buttons intact though I had more than enough of a view to make my cock twitch in the cage.

I watched as she grabbed a wine glass and told me about her dinner with her friends. She seductively poured her glass and pulled her hair free from the bun it was wrapped in. Her silky hair fell to her shoulders as she seductively ran her hand through it. She finally asked the question I was dreading.

"So how did it go with Lela?" She asked as she sipped her wine.

I hesitated but told her, "We met up and talked. She told me I should be allowed back there tomorrow night."

Jenny walked to the table as she unbuttoned her jean shorts, "Well I figured she would get you back. Here you go," she said as she seductively lowered her shorts and bent over the table.

I stood mesmerized as her tight ass swallowed a maroon thong to match her bra. I snapped out of it and asked, "What are you doing?"

Jenny finished unbuttoning her shirt and allowed her shorts to fall to the floor, "Well if you're back with Lela then you just came here to fuck me. So fuck me right here. No point in waiting. This way you can run back to her quicker."

She looked fucking incredible bending over the table in her bra and panties but I didn't like her attitude. I grabbed her from behind as she gasped in excitement but I wasn't going to fuck her. Well I couldn't with the cage.

"Oh shut up Jenny. I didn't come her just to fuck you and leave. You knew damn well I would end up with her. I really like you and want to have a good night with you. You know I have feelings for you."

"Please don't play me Matt. If you're lying you can just leave," she said as she turned and sat on the table.

She tilted her head to the side allowing her hair to fall off her shoulder. She looked more amazing than ever as her tight satin bra was obviously too small causing her large breasts to basically fall out.