Holiday

Stories and fantasies about rainwear.
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blackmacjay
Posts: 707
Joined: February 4th, 2010, 7:32 pm

Holiday

Post by blackmacjay »

It had become obvious that the lady wanted a more exotic sex life than before.

And it was becoming certain as she lay on the bed that first morning with her Mr. Buzzy and masturbated hard that her words were saying it all.

“I love you but I want more than you can give,” as she thrust the rapidly moving dildo in and out of her pussy and squirmed her hips around in anticipation of the orgasm that had to be coming. In just another minute or two, her head went back and her eyes showed the deep feral need she had.

We talked later and I suggested Dave because her exotic need was there and we were having dinner later that day. Her eyes showed that she was thinking about it as she mentally took off his pants and her hand strayed back to her pussy yet again.

At about 6:30pm they arrived to take us to dinner and Ginny continued to get ready although I was banned from the bedroom and I could not see what was planned. Over a quick drink and while his new girl friend went to the bathroom, I took a chance and asked him. Surprisingly Dave agreed but he insisted that he must tell Melissa all about it. And, as it turned out, she was even kinkier than he.

About 10 minutes later, I went to look for Ginny and was told that she would join us in the living room. While I did that, it was obvious that Dave had told his girlfriend about the plans and you could tell by the look on her face that she was even keener on this than I thought.

Then Ginny entered and I could see her black rubber-lined satin mackintosh which was fastened up to her neck strap and that all the buttons and her belt were tight around her body so that her breasts were flung forward against the rubber lining. Below her mackintosh were high-heeled boots that she did not think she could wear but she had on this very occasion.

The drive to the restaurant was over quickly in the cab we’d hired but I knew that if we’d been in my own car, the trip would have been more exotic. When we arrived at the restaurant, Dave and I had a drink while Melissa took Ginny to the bathroom as she was determined to find out what was planned.

On their return she told Dave what she had found out. Put precisely, Ginny had on a pair of crotch less panties, a waist-cincher garter belt which supported fishnet stockings under her high-heeled boots and Melissa had a latex suspender belt with 4 straps for each leg and a black bullet bra which she loved as she could push out her tits to an incredible extent.

The dinner was pretty much a normal affair except that Dave’s hand kept leaving the table to go underneath and play with whatever came to mind.

Going home in the cab was a little more imaginative as I sat in front while Ginny was in the back with Dave on one side and the Melissa on the other. Maybe the amount of wine was responsible for some of the giggles and suppressed laughter from the rear.

As we entered the front door, Melissa whirled Ginny wound and gave her a kiss on her mouth while at the same time she held her bottom that was covered by her mackintosh. I could tell, or I thought I could tell, that she was taken aback as she raced into her bedroom and closed the door behind her.

So the 3 of us had a cocktail while we were waiting and as I handed out the drinks, Ginny returned still in her mackintosh and high-heeled boots. The mackintosh was still buttoned up and tightly belted and so I wondered what had she been up to. She walked over to Melissa, opened her mouth and returned the kiss she’d been given while her hands took the girlfriend’s hands and placed them on the large and substantial breasts she had.

It took only a few moments for the girlfriend to start undressing Ginny. First she found the belt that she untied and then she slipped her hands inside the buttons and found Ginny’s garter belt which she played around with as she moved down to her pussy which was wet and so ready. Then Ginny began to undo the mackintosh buttons and when she was done she opened the coat displaying her half bra and the rest of her body but she was determined to keep the mackintosh too as a partial covering. I knew that she loved the rubber-feel of the lining and would not give up on that easily.

In an instant, Melissa pulled down the half bra and Ginny’s tits were open to the world as Dave went behind her to caress her breasts. He got her nipples between his fingers and squeezed them as he lifted them so that his girlfriend could seize them with her lips and pulled them out as she sucked them. And, all the time she caressed her pussy with her fingers and squeezed her clitoris.

I thought that she would come but she slid to her knees and placed her hands out in front but the mackintosh stayed on. Dave knelt behind her and lifted the rubber onto her back and began to knead her pussy and her ass.

Then Melissa pulled open her skirt and Ginny could just reach the lady’s pussy with her tongue. Slowly but surely Dave’s cock was rising and began to ease its way into her pussy. Then it was in and I could see Ginny wanted as much as she could get as her hands went down and lowered her erect tits almost to the floor and began to thrust in tune with Dave’s push and withdrawal.

Melissa removed her blouse and her bullet bra was thrusting forward while she showed the latex suspender belt she wore so proudly and stood behind Dave. She rested one bra cup on either side of Dave’s head while one hand slid down and held his balls that helped him to thrust. Slowly she pointed her finger at the ass just above where Dave was thrusting. He got the message and moistened Ginny’s ass and began to finger her.

Dave moved his hips into position so that he could fuck Ginny’s pussy from behind and entered her cunt with his cock while keeping a finger in her asshole.

Actually the double penetration felt good to Ginny and she started to rotate her ass in circles. Dave continued to fuck her doggy style and finger her ass, and then with his free hand he began to diddle her clit. Ginny could feel her orgasm building and then she started to hump her ass uncontrollably. Her orgasm was violent and audible as she pushed her cunt back toward his cock and yelled for Dave to fuck her.

As Ginny slowly came back to reality she realized that her ass was very full. Apparently during her intense orgasm Dave had moved his cock from her cunt to her asshole and allowed Ginny to impale herself on it while she was humping out of control.

Ginny freaked out and tried to pull away but Dave was too strong and he held her in place. Dave had not fully penetrated Ginny’s ass as he was fucking it slowly and gradually feeding more of it to her. 



"Dave, please take it out. I've never done this. I don't want to do this," Ginny pleaded but to no avail.
"I'm your first then. That's great! Now just relax and enjoy your first butt fuck," Dave told her. Ginny just closed her eyes and let it happen.

For what seemed like an eternity Dave fucked Ginny’s ass and she could feel it being stretched with each thrust. She became accustomed to his girth and adjusted to the full length of his cock in her ass. He caressed Ginny’s ass as he fucked it thoroughly and she had never felt so full in her life. Ginny was impaled on his huge cock and she tried to relax and placed her head down on the mattress.

This position emphasized Ginny’s shapely ass and Dave told her how good looked she in this position with his cock sliding in and out of her asshole. 



"You really have a beautiful ass Ginny. I love fucking you in the ass and I am going to look forward to more of this," he said. 

"I am going to go in your ass and fill it up with my cum," he confidently announced. 



Ginny could feel Dave’s cock getting larger in her asshole as he approached his orgasm. His cock swelled and he fired barrage upon barrage of cum into her ass. Ginny could feel her ass flooding with her first sperm enema. It leaked out of her ass and ran down the inside of her thighs and over her pussy. Dave removed his cock from Ginny’s ass with an audible pop and she felt a rush of cool air enter her gaping asshole. 



He was totally in control of her at this point and knew she would do almost anything including making love to his girlfriend.

Ginny now stood up and tightened her black satin mackintosh around her and left the living room while Melissa followed her as well. Just about the only person who had not had an orgasm was me although, while Ginny was being fucked, I had played with my cock for a while. Dave, on the other hand, was dead on his feet and crawled over to the couch for a well-earned rest.

A few minutes later Ginny and the girlfriend walked back into the living room. Ginny’s mackintosh was still belted tightly which showed off her breasts beautifully but Melissa wore a polished rubber garment which it turned out was made with rubber on the inside also. This too was belted tightly but it was obvious that the mackintoshes were hiding something hidden on the inside.

The girlfriend put her arms round Ginny and pushed out her tongue as Ginny opened her mouth to receive it. Then she reached between the mackintosh buttons and pulled out her dildo that was inside. And Ginny followed suit. So there they were, the 2 ladies kissing each other as they played and stroked the other’s dildo.

I should have known what was coming and, as usual,
I had prepared myself by always shaving the hairs of my genitals and ass

Ginny leaned back against the door and the black satin mackintosh beckoned. My eyes dropped to her pelvis as I remembered that she was already strapped and ready to go. I could feel my penis throbbing with desire as I looked upon her.

I managed to ask, weakly, when Melissa would be joining us but Ginny told me that the girlfriend had decided to wait until the last minute. I wanted to know if it was OK for us to fuck alone to which she answered by walking over to me, placing her hand behind my neck and pulling my mouth to her breast while her other hand began undoing my pants. I helped her to remove my pants, soon followed by the rest of my clothes. Once we were both naked we hugged each other close and I felt the press of her breasts against my belly and the coolness of her strap-on against my legs.

She then took me by the hand and led me up the stairs to their bedroom. Climbing the stairs I could not pull my eyes away from the curves of her body nor the sway of her strap-on. My own penis is six and a half inches long and an inch and a half across. Her "cock" seemed to be about the same thickness, but an extra inch or so longer.

She sat me on the bed and began to suck my cock. My cock was so engorged with my arousal that every stroke of her tongue or touch of her lips sent shivers throughout my entire body. As she brought me closer and closer to the edge I reached down and held her breasts in my hands, lightly stroking them and teasing the nipples into erections. Ginny began to work my cock in earnest and I could feel pre-cum dripping freely into her mouth. Suddenly my balls contracted and I felt the beginnings of the largest orgasm that I had had in recent memory. In that same instant, she stopped pleasuring me and yanked hard on my scrotum. I yelled in pain and my orgasm was stopped in its tracks.

Ginny, then slapped me in the face and told me to flip over on my belly. I turned over, complying more out of shock than anything else. The moment I did, Ginny drove her tongue into my ass and slathered it with saliva for a good few minutes. She then pulled out a pump bottle of lube from a nightstand and pumped it straight into my ass...cold.

This was quickly followed by her strap-on. Incredibly happy that I had warmed up with a butt plug while getting ready, I was able to take half of her length on her first stroke without too much pain. She began to work her cock in and out of my ass, and after about six strokes she had bottomed out. Without a pause she began pounding my ass, screaming and yelling like she was possessed. The shock and the sensations were overwhelming and I lost my erection.

Suddenly I was surprised to hear a moaning coming from the far corner of the room. Looking up I saw Melissa sitting legs spread, completely naked, on an easy chair. She was watching us intently while one hand plied her clitoris and the fingers of her other hand curled in and out of her pussy. I could see her fingers glistening in the light as she breathed heavily and continued to moan and mew. Watching her brought my dick back to life and this, in combination with Ginny’s anal assault, soon had me on the edge.

The woman began to wail and quiver her way through an orgasm and I could feel my own orgasm building strongly. Just as I was about to cum, Ginny pulled out and again pulled and squeezed on my balls, turning the tide. My legs were shaking as I began to stand up. Ginny began to giggle, with tears in her eyes, and she apologized for being so rough.

"I must have needed that" she confided, "I am sorry for taking it all out on you. Do not worry, Melissa and I will take good care of you". With that Melissa came over and I was able to see her fully. She seemed to be about 30 years old, with a slight but athletic build, pale skin, and long dark hair. Her large breasts had seen enhancements and each had a barbell horizontally piercing her nipples.

She knelt down and took my dick into her mouth and began one of the best blowjobs I have ever had the pleasure of experiencing. At the same time Ginny began to suckle one of my nipples while putting the middle two fingers of one hand into my mouth. After a few minutes Ginny pushed me back on the bed and Melissa followed. While Melissa continued to work me over with her mouth, she joined us on the bed, spread my legs and then slowly began to re-enter me with the strap-on. And all the time, I remembered the very first occasion where she had done that ……………..

I knew that Melissa had been able to fuck her incredibly butch ex-girlfriends with a strap-on, so why not me? Sure, they didn't take it up the ass, but I don't have a vagina so my options seemed limited. If those ladies were man enough to get fucked by Melissa wearing a strap-on, then so was I.

And there was the strap-on fastened to Melissa’s waist but after the strap-on arrived I was feeling more confident. It was not big. A few straps, a few metal rings, and a veiny, purple, dick-shaped piece of plastic about the size of two fingers. Taking that thing up the ass, it seemed, would be a cakewalk.

Soon I found myself bent over on Melissa’s bed, my chest pushed up against the mattress, while she strapped the harness around her long legs and smooth hips. When she penetrated me for the first time I tensed up and let out a long succession of soft, high-pitched "Ow"s. I was not off to a manly start.

"Are you ok baby?" she whispered. The strap-on was inside me but she wasn't thrusting. Instead she was leaning over me, her weight on my back as her fingers petted my face.

"I'm fine," I lied.

Melissa knew I was not telling the truth but her movements were gentle and deliberate as she started to slowly rock against me. “My Ows” dissolved into whimpering.

"Shhhh," she hushed, kissing my back, "you're doing such a good job."

But I wasn't doing a good job, and I knew it. The room seemed tight and close, and what I had thought of as a small piece of purple plastic now seemed large, long, and incredibly hard.
"More lube," I gasped.

It seemed to be the only words I could string together. That and "it hurts." When after a few minutes of extremely placid and unexciting anal sex, I said the former for about the fifteenth time, Melissa stopped her slow thrusting.

"There is no more lube."I looked over my shoulder and she held up the empty container. She had been lubing me every time I asked for it and we had gone through four ounces in five minutes. She leaned over me and gripped hard on my hip in order to distract me as she pulled out. I gasped again and rolled over on my side, too drunk and worn out to stay awake.

The next day my ass didn't hurt like all holy hell to my surprise, although I did notice an awkward feeling while sitting and I walked a little bow-legged. I definitely didn't feel like any less of a man for having been penetrated.

But I did feel like I had been a letdown. I was worried that I made a bad partner when I was the one getting fucked. I eventually found out that my performance was on par with an ex-girlfriend whose virginity Melissa had taken, but that was months later. At the time, I just felt like a punk who couldn't handle getting railed.

A month later I decided we should try it again. We were lying in Melissa’s bed after a bout of Sunday afternoon non-strap-on sex when I asked if she was interested in doing me in the butt. Melissa hadn't asked to screw me since the first incident and I thought the reason she was no longer interested in getting down with my ass was my poor performance. I wanted to make up for what a baby I had been. This time, I was determined to let my girlfriend do me up the ass right.

I got up on all fours while Melissa kneeled beside me and strapped on her extremely out of place plastic penis. The room felt open in the afternoon sunlight. "You ready baby?" Melissa was rubbing the strap-on up and down, as if she were giving herself a hand job.

Although we hadn't discussed butt sex since the first time, it seemed that she had been thinking about it. In her right hand she held an expensive-looking glass bottle, one that I would have thought contained perfume if I had come across it in a department store, as she lubed up with her left.

Melissa leaned over and squirted the lube on my ass. The bottle was full and much larger then our last one. Written in script lettering was the single word "Pink."

"You couldn't find a manlier-sounding brand?" I asked. She smiled and climbed behind me.
My bravado lost its footing at first. The initial pain was still sharp and I started whimpering immediately. I focused on not tensing up as Mac eased further inside me.

"More lube," I muttered. I don't know much about lube, but Pink certainly gets my seal of approval. The painful friction seemed to lessen. I started rocking back into Mac.

"Fuck," she whispered. She picked up the pace, thrusting into me as I came up to meet her. My whimpering was replaced with gasps and cursing.
After a few minutes, Mac slid her left hand around my waist and started to jerk me off. It caught me by surprise.

Reach-arounds were things I had joked about in high school, but now I didn't feel like laughing. I was getting a reach-around with my girlfriend's no-longer-thought-of-as-little purple dildo in my ass, and it felt incredible.

She became less gentle. She gripped my side with her right hand as we moved back and forth. I looked over my shoulder and she was smiling, sweating, and gorgeous as she repeated over and over what a good job I was doing. She rubbed my dick as we moved faster. I exploded all over the bed sheets, and we collapsed.

It's been five months, and despite that afternoon's success, Melissa hasn't mounted me from behind since. She enjoys it, but points out that given her penis is a piece of plastic strapped to her crotch, it doesn't exactly overwhelm her with physical sensations. While the same definitely isn't true for me (I certainly have physical sensations), getting fucked in the ass is still not my favorite sex act. It's one that I'm down with, but not one that I find myself pining for.

Friends find it interesting that I, a straight male, agreed to take it up the ass not once but twice, and would willingly do so again. My immigrant grandfather thought that clearing the dinner table was a womanly act. I reason that since I clear the table and do the dishes, getting fucked by a woman wearing a strap-on doesn't rob me of my manhood either.

For me it wasn't a sexual orientation thing, or a power thing: It was just a sex thing. And if Melissa feels like sliding her long legs into that harness tonight, I'll be more than happy to get on all fours and take it in the ass like a man.
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