Sissies Strapon
I had just moved into a new town due to finding a new job. My girlfriend of several years decided she did not want to follow me to the suburbs of London and so we decided to break up. It was painful for the first few months and I became very lonely. I began to drink often at night and one night I went to my neighbors apartment under the the pretence of needing a corkscrew to open a bottle and asked if she wanted to join me.

Adrianna was in her early 30’s and very sexy with long hair and a very sexy figure. She had gorgeous breasts and was very confident about who she was. I liked her immediately and I think she liked me. Despite the 10 year difference in our age or perhaps because of it. We hit it off right away. I enjoy the company of an older woman and the wisdom she had and she enjoyed my youth and energy and my willingness to please her.

I began to go over to her house on a regular basis and drink wine. On my 3rd or 4th visit, once we had gone through a bottle of red wine, she asked me about my sexual fantasies. I was a little shy and told her so.

“It’s ok Shaun, I’m not going to tell anyone. I am very curious about these things and tend to be rather kinky in my sex fantasies, and often wonder if other people are too, but they are too shy to speak up about it.” Adrianna said.

“Well, what specifically do you want to know?” I asked.

“Do you have a sex fantasy that you often think about when you masturbate? “

“It varies but I have a few that always work for me, however I am not very comfortable sharing them.” I said.

“Have you ever actually done these sex fantasies that you think about?” Adrianna asked.

“Once, but it upset the balance of the relationship and I didn’t like it.” I explained.

“I understand. Well, please tell me Shaun, you have nothing to lose with me, and I am very interested.”

“Well, sometimes I fantasize about dressing up as a woman, and having sex with my partner.” I sheepishly said. It felt great to say it and I blushed and because aroused.

“I think that is wonderful and playful and sexy. I also enjoy dressing my lover up in my sexy underwear and putting makeup on him. It turns me on to see him like a sissie and feminine.” Adrianna said.

And that was as far as we took the subject for several months.

My computer broke, and I began to go over to Adrianna’s place each morning to check my email. We would have coffee together and touch base with each other. She would be wearing silk gowns or lacy short camisoles and I was often aroused but too shy to do anything. One morning, she left to go for an appointment and I stayed at her place. I went into her closet and began to dress myself in her panties, stockings, garter, and put on her bra and a silk robe. It smelled of her and turned me on very much. I sat down at her computer and began to search for images of a man being dressed up as a woman and then fucked with a strapon dildo. I masturbated in her pink panties and then got undressed and took a shower.

When I got out of the shower, Adrianna was home, sitting at her computer and it was then that I realized I had forgotten to close the images of the sissies strapon fucking I had been looking at. I felt extremely embarrassed. Had I been caught?

“Shaun sweetie, come over here for a second.” Adrianna said. “Have you been looking at these pictures on my computer?”

“Umm, yes Adrianna, I have. I am very sorry, I didn’t know you were coming home so soon.” I explained.

“Now honey, I don’t mind you using my computer, but you should have told me you were going to be looking at these things. I would have liked to look at them with you. Do you understand? “

“Yes Adrianna.” I said.

“Also, I noticed that someone has been going through my closet and my favorite pair of pink panties are missing. Any idea where they are Shaun ?”

“I am so sorry Adrianna, I am so sorry. Please don’t be upset.” I begged.

“Shaun, I wish you would have asked me cause I would have been more than happy to help you pick out something sexy to wear. But because you went behind my back, I am going to have to punish you. Now come over here and lay down across my knee.”

I walked over to Adrianna and lay down on the bed across her lap. She pulled down my towel and began to spank me firmly about 10 times. I enjoyed this far too much and did not complain one bit.

“You like this don’t you? I can feel you getting very hard. Shaun, you mentioned before that your fantasies upset the balance of your previous relationship right? Well, lets begin our relationship properly ok?”

“Ok Adrianna.” I stuttered.

“You and I are going to be lovers, and I am going to be in control. You are going to be submissive to me and do as I say regardless of wether or not you like it or not. Agreed?”

“I’m not sure Adrianna.”

“Are you scared? Don’t be scared. I know deep down this is exactly what you want. It won’t make you any less of a man, but it will make everything far more pleasurable. After all, I am 10 years older than you and know a bit more about pleasure. Agreed?”

“What are you going to do to me?” I asked.

“Everything that you have ever fantasized about and more.”

“I’m a little afraid Adrianna.”

“Well lets try it, and if you don’t like it, all you have to do is say so, and we will stop. Ok?”

“Ok Adrianna, I’ll try”

“Good boy.” She said.

Adrianna took my hand and walked me over to her closet. She picked out some purple panties, some white stockings and a garter. She dressed me in that and then found a pair of red high heels. She took me by the hand and led me into the bathroom and sat me down in front of the large mirror and began to put lipstick on me and make up and eye shadow. Then she put a bra on me and stuffed it with tissue.

She told me to stand up and turn around and look at myself in the mirror.

“How do you think you look?”

“I would fuck me.” I said.

Adrianna laughed and said, “I would too.”

“I want you to allow all your masculinity to go, and fall into the soft sweetness of being feminine. I want you to think about responding rather than acting, and give yourself over to me entirely. Feels good doesn’t it? To be so juicy and delicious?”

“It does feel very good Adrianna. I feel very relaxed, a little embarrassed, but very excited too. “

Adrianna led me over to the bed and we lay down next to each other kissing. Her tongue penetrating my mouth. She tilted my head back and her lipstick met with mine. It was a wonderful sensation. We both smelled of flowers and sensuality. I was so hard, my cock was sticking out of the tight panties I was wearing.

“You are my little sissy aren’t you sweet boy? Do you know what a sissy wants more than anything? Yes I think you do.” Adrianna said and reached over to the night stand and pulled out a 7inch black dildo. “Do you know what to do with this? “

I placed my lips on the black dildo and began to suck it. Adrianna took the back of my head and controlled the up and down motion, at first slowly, and then faster.

“Have you done this before?” She asked. “You are quite good at it.”

I kept sucking on the cock and I worried I might cum too quickly. Adrianna slowly pulled the cock out of my mouth and placed it in a strapon  harness.

“My little sissy, I know what you want and need. And you know it too. I want you to strap this on my hips.”

I strapped on the dildo to Adrianna’s hips and watched how large it was as it swung from side to side. I could not believe it was going inside of my arse. However I was willing to do anything for her at that moment.

Adrianna then took my hand and walked me over to her desk. It was difficult to walk in high heels. She bent me over the desk and tied my wrists to the legs of the table and tied my ankles to the bottom of the other table legs. I then felt a cold liquid in the crack of my arse. She was putting lubricant there.

“You are very tight and are going to need this. In fact, it is going to be very uncomfortable for you for awhile. I am going to give you a butt plug to wear around the house and this will make anal sex less painful. But for now, you are going to have to take it like a man. Understand?”

“Yes Adrianna. Be gentle ok?”

“I think its time you started calling me 'Mistress Adrianna' now Shaun, dont you?”

“Yes Mistress Adrianna” I gasped.

As the strap on went into my sissy hole, I felt a wonderful sensation. It was huge but it touched my prostrate and made me so hard. I told Mistress Adrianna I was going to cum. She kept going deeper and deeper into my arse and soon I had an orgasm all over the desk.

“I’m not done yet sissy boy.” Mistress Adrianna said.

Deeper and deeper, faster and faster, I began to hear Mistress Adrianna have several orgasms as the large dildo massaged her clit and penetrated my ass. She moaned and screamed and when she had had enough, she slowly pulled the cock out of my tight arse.

“Very good for your first time. Next time, I will place a cock ring on you so you don’t cum so fast. Now I want you to take a shower, and when you are done, I want you to put on the clothes I lay out for you and come to my bedroom. Ok sissy boy?”

“Yes Mistress Adrianna”. I said.

Mistress Adrianna had laid out fresh lingerie for me and I put on the white panties and pink nightie and met her in her bedroom. She was standing at the end of her bed in a tight revealing PVC dress, thigh boots with silver toes and heels and a huge black strapon dildo that made the previous one look tiny. I was hard almost immediately.

“Get down on all fours bitch” she hissed at me with an evil grin “It's time for you to learn what being my sissy slut really entails”

I gulped as the enormous reality of what I had let myself in for started to sink in, but immediately relaxed as I felt Mistress Adrianna's hands on my hips as she guided the huge strapon into my arse. I felt fulfilled and that I had finally found my place in life, impaled on my Mistress Adrianna's sissies strapon cock.

I never knew that being a sissies strapon slut could produce such wonderful feelings, as well as create a unique bond with my Mistress.

Sissies strapon lover.
EXISTING MEMBERS LOGIN
JOIN MY MEMBERS AREA
Mistress Strapon
Strapon
Mistress Adrianna (c) 2004 | 2009 all rights reserved