Kinky Sex Stories

Strap on sissy sex story

I just moved into a new neighborhood due to finding a new job. My girlfriend of several years decided she did not want to follow me to the suburbs of Portland and so we decided to break up. It was painful for the first few months and I became very lonely. I began to drink wine often at night and one night I went to my neighbors house and asked if she wanted to join me.

Diann was in her late 40′s but very sexy with long blond hair and a tall build. She had rather large breasts and was very confident about who she was. I liked her immediately and I think she liked me. Despite the 20 year difference in our age or perhaps because of it. We hit it off right away. I enjoyed 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 Pinot Noir, she asked me candidly about my sexual fantasies. I was a little shy and told her so.

“It’s ok John, 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.” Diann 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?” Diann asked.

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

“I understand. Well, please tell me John, 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 lover.” I sheepishly said. It felt great to say it and I blushed and because aroused.

“I think that is wonderful and playful and fun. I also enjoy dressing my lover up in my sexy lingerie and putting makeup on a man. It turns me on to see him docile and feminine.” Diann said.

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

My computer broke, and I began to go over to Diann’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 teddies and I was often aroused but too shy to do anything. One morning, she left and I stayed at her place. I went into her closet and began to dress myself in her panties, stockings, garder, 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 strap on dildo. I masterbated in her pink panties and then got undressed and took a shower.

When I got out of the shower, Diann was home, sitting at her computer and it was then that I realized I had forgotten to close the images of the sissy being fucked with the strap on. I felt extremely embarrassed. Had I been caught?

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

“Umm, yes Diann, 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 Diann.” 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 John?”

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

“John, 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 Diann and layed down on the bed across her lap. She pulled down my towel and began to spank me gently 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. John, you mentioned before that your fantasies upset the balance of your previous relationship right? Well, lets begin our relationship properly ok?”

“Ok Diann.”

“You and I are going to be lovers, and I am going to be in control. You are going to be submissive however I will never do anything that you don’t want me to do. Agreed?”

“I’m not sure Diann.”

“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 20 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 Diann.”

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

“Ok Diann, I’ll try”

“Good boy.” She said.

Diann took my hand and walked me over to her closet. She picked out some ruffly purple panties, some white stockings and a garder. 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 asked 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.

Diann 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 Diann. I feel very relaxed, a little embarrassed, but very excited too. “

Diann 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.” Diann 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. Diann 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 worried I might cum too quickly. Diann slowly pulled the cock out of my mouth and placed it on a 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 Diann’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 ass. However I was willing to do anything at that moment.

Diann 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 ass. 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 Diann. Be gentle ok?”

“I will my lover.” Diann assured me.

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 Diann I was going to cum. She kept going deeper and deeper into my ass and shortly I had an orgasm all over the desk.

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

Deeper and deeper, faster and faster, I began to here Diann 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 butt.

“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 bed. Ok sissy boy?”

“Ok”. I said.

Diann had laid out fresh lingerie for me and I put on the white panties and pink teddy and met her in bed. We had a glass of wine and talked and she massaged my back. I was truly falling in love and wondered why I had not done all this before. We kissed deeply and one of her fingers found it’s way into my ass. I was hard almost immediately. Diann pulled me closer to her and inserted my cock into her wet pussy. She got on top of me and fucked my cock until she came. Then she rolled me over and inserted my cock again into her pussy and instructed me to fuck her softly, gently, and like the sweet sissy that she loves very much. She controlled my body and my motion the entire time, not allowing me to get too excited and keeping me from cuming. She was in complete control and it was turning me on far more than I thought it would. Finally, she allowed me to cum but before I did, she rolled me over and placed her lips on my cock. I exploded into her mouth and she swallowed it all. Then kissed me gently.

I never knew that being a strap on sissy slut, could produce such wonderful sex, as well as create a unique bond with my lover.

The Strap on Sissy.