📚 mr. and mrs. flannegan Part 2 of 2
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Mr And Mrs Flannegan Pt 02

Mr And Mrs Flannegan Pt 02

by plus_sized_sissy
16 min read
4.46 (14800 views)
adultfiction

Mr. and Mrs. Flannegan Part: 2

I awoke the next morning still in a haze, questioning if the previous night's events had really taken place. Looking over at the night stand I picked up my phone and went to my messages. Looking through them I confirmed this did in fact happen.

The next couple of days were uneventful. I did not see any sign of Mrs. Flannegan, and was too nervous to go to their house to use Ted's equipment. Mr. Flannegan returned from his business trip and life continued as usual. With Mr. Flannegan home I returned to using Ted's pc.

One night while I was in Ted's room gaming on his computer his mother came in and sat on the bed behind me, quietly waiting for me to finish. I turned around shortly after and as I start to speak she interrupts me and says "Hello Josh, As you may or may not have noticed, Mr. Flannegan is out on business and will not be back till tomorrow morning." As she speaks she fiddles with a piece of paper in her hands. "Now being a woman of opportunity I figured what better time to come check on my son's good friend Josh" she giggled. Turning the paper over in her hands I was stunned in fear realizing the contents that lie upon them. To my horror on the paper was photos, taken from the day Mrs. Flannegan came to my apartment.

The pictures showed crystal clear images of me, standing in front of the couch in a woman's thong, My penis fully erect as I had just finished in Mrs. Flannegans mouth. The pictures were damning as she was nowhere to be found in them. Confused as I saw her put her laptop away, I looked up from the pictures in front of me to speak. A wide grin was apparent on her face as she watched me squirm and blush looking for the words to speak. Before I could find them she asked "My dear Josh you must be wondering how I acquired these photos." As she spoke she lifted her bag up off the table, flipping it upside down. As she did this it became obvious that a camera was sewn into the fabric of the bag, Recording our every move.

"Now Josh, I wonder what Ted would think knowing his friend Josh was a panty wearing sissy.. Do you think he would continue to be your friend knowing you not only wore a woman's thong, but you had a cute little boner to go with it? What would that girl at the movie store you always talk to think? What was her name Jessica? I see you eyeing her up from the aisles, too afraid to approach her."

Scared out of my mind I looked at Mrs. Flannegan with pleading eyes. "Please Mrs. Flannegan, please dont' show anyone. What can I do to make you delete these pictures and the video?" I asked frantically. Giggling at me she looked me back in the eyes, knowing she had me defeated. She said, "Well my pretty young lady, I'm glad you asked! You see I have been pondering upon the same exact question and I do believe I have come across a good solution."

"I have come up with a list of things that I will require before I let you go and delete these photos. All of which will be completed here, and now." she said as she flipped to the second page in her hand. "First you will come with me, I will run you a bath and we will shave off that icky boy hair plaguing your legs and chest, not that there is much to begin with. Second, when I have finished shaving you, I will dry you off and lead you to the second spare bedroom."

"We have always kept this room locked, The reason being that the stuff inside belongs to Ted's cousin. I'm sure you have heard plenty about her, as it just so happens you both wear roughly the same size. It is simple, I will present you another pair of her panties. You will put them on and model them for me. After which you will start your third and final task. You will pleasure me properly. When all of this is completed I will reward you IF, you are good."

As she spoke I knew I didn't have a choice. My cheeks burned red with embarrassment as she commanded me to follow her to the bath. Inside the room I was told to take off all my clothing. Setting them aside as the bath finished running I looked at her waiting for her to leave the room. Looking back at me with amusement she grinned, "Well, what are you waiting for my dear? I'm not going anywhere, remember? I said that I was going to shave you. I said nothing about you doing it yourself. How am I to know if you are doing it properly? I would hate for you to hurt yourself." she giggled.

For the hundredth time my cheeks burned with embarrassment as I stepped into the bath. For the next half hour she ran the razor all over my body from the neck down. Then she had me step out of the bath. "Can you pass me the towel?" I ask. "No my dear, you are not finished yet. Come here and bend over the sink." she said. Hesitant I moved forward to the sink, as I arrived in front of it she placed a hand on my hip and one on my back bending me over the sink. "Grab onto the sink for balance" she said.

Grabbing onto the sink she stepped back grabbing the razor, running it up my butt cheeks. I let out a yelp as I felt her fingers spread my butt cheeks apart. She giggled and ran the razor up and down my crack, shaving me to completion. "A woman always shaves her pussy." she giggled as she handed me the towel. Amused at how easily she could make me blush.

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"Now come with me Josh it is time for stage two of our evening of fun together." She led me through the house to the guest bedroom unlocking it, pulling me inside by my hand. Sitting me down at the chair in front of the desk I quickly realized it was a vanity. "I know I said you would only be wearing the panties again but seeing you all smooth I can't help myself but go all out." As she spoke she applied make-up to my face.

Fifteen minutes later and she had finished. "You look amazing Josh. Come and sit on the bed" she said as she moved me to the bed. Turning to the closet and dresser she started to pull out clothing one by one. First she took out a set of hot pink lingerie with black lace trim and laid them on the bed. She continued her search as she pulled out a pink sundress and laid it on the bed by the lingerie.

"Alright Josh. You are going to put these clothes on. If you do everything that I say, I will reward you as well as delete those photos. Here is some lingerie you are to put on under this sundress. Put them on slowly now while I watch." Nervous, I watched as she grabbed the stockings moving in front of me. She said "I want you to notice how they feel going up your silky smooth legs my dear." handing them to me. Blushing, I Took the scrunched up stocking and began rolling it up my legs.

The sensation was astounding. The connection between the fabric and my skin was unlike anything I had felt. As I got to the top pulling it as far as it would go she handed me the other one. I grabbed it from her and put that one on slow like she told me to, feeling the fabric slide against my smooth leg once again. As I got to the top I looked down. To my shame all these new sensations mixed with this beautiful woman standing here watching me had caused the blood to rush to my small cock.

"Oh my Josh, what is happening down there?" she giggled as she pointed to my penis. Blushing, I turned away as she giggled. Picking up the garter belt she handed it to me. I slid it up to my hips and connected the straps to my stockings. Next she handed me the panties. Frilly as can be I slid them up my stockings until they sat in place. My penis strained against the fabric, trying to break free.

Giggling at me she says "Poor thing, your tiny little penis is trying with all its might to fight against the girly feminine panties but it can't even muster to lift them off your skin." walking up as she spoke, she put her hand on my crotch rubbing me through the panties and giggling. "Now for the dress!" She said as she removed her hand, picking it up and helping me into the dress. Zipping it up in the back she sat me down at the vanity again. Facing away from the mirror. Returning to the closet she pulled out a wig of blonde hair. Walking back to me she fastened it onto my head, adjusting it so it was just right.

Satisfied with her work she turned me around towards the mirror and said "Look how pretty you are as a lady Josh. You sit here and admire my handy work while I arrange some preparations." With that she left the room. Leaving me to sit in front of the mirror I was shocked. I couldn't recognize myself, I couldn't believe I was staring at a mirror. What was in front of me was a beautiful girl. Stunned, I said nothing as she returned. "Come, now young lady" she spoke with authority.

Wanting the pictures to be deleted I eagerly Got up and left the room with her. I followed her until we reached her bedroom. Near the bed was a small table. A tray of ice lay on the table. She led me to the bed near the table and sat me down on the edge of the bed. Lifting my dress she took my panties to the side exposing my semi-erect penis. Taking the whole thing into her mouth she sucked up and down till I was hard again. Satisfied she placed my penis back inside the panties and pulled my dress back down. "Be right back." she giggled, and left the room.

My mind was in a sexual haze. While I knew all this was wrong, I couldn't help but be completely controlled by this stunning woman. Her power over me was absolute. As she returned I noticed she wore nothing but a black set of lingerie. Walking over to me she had me stand and move to the side. In a drawer in the table she pulled out a knee pad and placed it in front of the bed. Lowering the table she sat on the edge of the bed facing me and the pad.

"Now my little sissy girl, the time has come for your third task. As you notice my panties are already gone."she said lying back. "Your job today is to help me finish." Spreading her legs she motioned me forward, my task obvious. I knelt down on the pad and leaned forward making out with the lips between her legs. Feeling completely at her mercy as she grabbed my head grinding against me.

Suddenly as I continued she pulled my head back forcing my face off of her. "Grab some Ice my dear." looking at the tray of Ice I grabbed out a piece. "Now you are to put the ice inside of me." she said. I took the ice and slowly inched it inside of her, the ice disappearing without a sound. Moaning, she tilted her head back and said "two more should do it, go on more ice." sliding two more pieces inside her, I looked back up at her awaiting my orders.

"Continue eating me what are you doing dear" she said, shoving my face back into herself and holding it there. I made out with her sex like my life depended on it. She grabbed my head again pushing it against herself as she tensed up more and more. Tilting her head back she moaned out as she came. Struggling to breathe I kept my tongue out like she said, holding onto her thighs for dear life.

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As she finished she released my head and I fell to the floor. Standing up she said "Excellent My sissy, you have done well. There is one last task awaiting us. You will now model that outfit for me! Now stand up and bend over the bed." I complied, bending over the bed. "Look at me, slave." she said. I turned my head so I could see her behind me. "Look me in the eyes and tell me you love being my little sissy girl." I felt so vulnerable in this position. Completely at her mercy.

Feeling my face burn red I repeated back "I love being your little sissy girl." "Good girl. Now say, I love to dress as girly as possible and prance around like a princess all day long." Her smile was as wide as possible as she looked down at my vulnerable predicament. I hesitated and was embarrassed by what I was told to say. A smack pierced the silence followed by a sharp pain in my right butt cheek. "SAY. IT. NOW. SISSY." she said with force.

"I LOVE TO DRESS AS GIRLY AS POSSIBLE AND PRANCE AROUND LIKE A PRINCESS ALL DAY LONG!" I cried out hoping she wouldn't spank me again. "Good girl." she said, caressing my butt. "Now, you've been a good girl. Good enough for a reward. Stand up and sit down on the bed facing me." I hurriedly complied trying my best to avoid another spanking as my butt cheek hurt like never before.

As I sat down she knelt in front of me flipping my dress up. Pulling my panties to the side revealing my tiny erection. She held it in her hand as she looked up and she said "It's okay Josh, I know that you will never be able to please a woman the way she wants with this thing. But we I've shown you you can still be of use even without using this tiny pathetic excuse for a penis" she giggled as she placed her mouth around it before I could speak.

Taking me all the way in her mouth with ease she sucked up and down. The feeling was like no other and I could feel an orgasm already rising from within me. Looking down I could see her staring into my eyes as she sucked up and down. The stimulation was too much as I grabbed the bed unable to hold back. I felt jolt after jolt as I came in her mouth. She continued to suck me till I was completely finished, never breaking eye contact. Then she stood up leaning over me with her hands on my knees and before I knew what was going on kissed me.

Thrown off as her tongue invaded my mouth it tasted salty. As I felt her move her tongue around inside my mouth I realized it. She had kissed me with my cum still in her mouth and was pushing it into my mouth. She must have realized my hesitation as she grabbed the back of my head holding me in place as she pushed the rest of my load into my mouth. Stepping back as she deposited the last of the load, she looked at me "Open your mouth now Josh. Show me the cum." She said, looking at me expectantly. I opened my mouth showing it to her. "Good. Listen to me. You are to swallow it all. Savoring the feeling as it goes down your throat. NOW!!"

Reluctantly I looked her in the eye as I swallowed part of it. Feeling it go down my throat it felt like nothing I had ever drank. I swallowed little by little as the taste overwhelmed my senses. When I finished she moved closer and grabbed me by the back of the head as I knelt so I was looking directly up at her. "Open up sissy so I can make sure you have swallowed all of it." I complied and opened my mouth for her looking up. She leaned in looking closer and spit, right into my mouth. Giggling, she released my head and said "Good girl."

"As promised I will be deleting the video and photos that we took at your apartment. However I regret to inform you Josh that this room is FILLED with cameras. We captured every angle of our night of fun!" she said, pulling one out from behind the pillows on the bed.

Horrified, I looked up at her in protest "but you promised me!" She scoffed and said "and I followed through with my end of the promise my dear. I never said I wouldn't be recording our time together tonight nor did you ask! I simply recorded it for one purpose and one purpose only." she said as she towered over me. "I own you now josh. For the rest of the year and foreseeable future you will go wherever, whenever I say. You will do what I tell you without protest, Or else perhaps copies of you bent over the bed telling me how much you love being a little sissy will show up all around town..."

As the information settled in I realized I was fucked. If anyone saw that video I would be ruined. I was truly owned by Mrs. Flannegan now. "Fine Mrs. Flannegan I will do whatever you say. Just please, don't show these videos to anyone please I'll be ruined" I cried out. Looking down at me kneeling in front of the bed she said "Hush now my pet. As long as you do everything I say I will not let any harm come to you. I will keep these videos as insurance that you will do exactly as I say. If you are a good girl for me they will remain just that. Disobey and well..."

She walked to the doorway as I started to lift the dress off. "What are you doing? She asked" I dropped the dress back down and said "I thought we were done so I was taking off the dress." Giggling she looked at me "nonsense my dear you are to leave it all on till the morning. You will sleep in Sarah's old bed(Ted's cousin). My cheeks burned red once again as I became very aware of how girly the outfit I had on was. "I will decide in the morning if you deserve your boy clothes back or not. Now get in bed." she snapped.

I took back the pink blanket made of pink faux fur and climbed into the bed. The underside of the blanket was velvet, the sheets satin. This was clearly a woman's bed. All of the fabrics were so girly and caused my face to burn with embarrassment. I looked up at her as she spoke "Goodnight my dear Josh, get some rest. You will need it for tomorrow" she said with a wink, walking out the door and closing it. As I lay back wondering what she means the haze takes over, the mixture of fabrics lulling me into a slumber, I drift off to sleep.

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