Bob, Jennifer, and Me

My wife, Jennifer, and I have always had a wonderful sex life. But sex had always been rather routine and middle class, lots of missionary fucking with some of her on top and me from behind. On several drunken nights she let me penetrate her asshole after lots of pleading on my part, but it always hurt her too much and we ended up going back to regular sex.

This all changed when I bought some sex toys from Adam and Eve and a massage table from a seller online. After several glasses of wine and lots of erotic massage, my wife would let me have my way with her on the table. I would start by gently rubbing her clitoris and entering one, then two fingers into her pussy. She would moan for me to put in another finger and then ask for the large vibrator.

On her stomach, she once moved her ass up and told me hoarsely, "Play with my asshole."

Wasting no time, I inserted my index finger gently, using lots of oil. At first she said it hurt, but after lots of gentle movement, her ass loosened up and she began to breathe heavily.

"Oh God, that feels so naughty," she moaned. "I never thought it could feel so good. Does it turn you on? Just play with my ass. Lick it. Put the small vibrator in it. Just play with it."

After several minutes she told me to put the large vibrator in her pussy while I continued to move my finger in and out of her asshole.

Within several minutes she had her first anal-assisted orgasm and our journey into a whole new realm of sex began.

After that, she demanded anal play more often than not when we fucked. If she were on top, she would insist I insert my index finger into her ass. On the massage table she'd beg for a finger in her ass while I stroked her clit or moved a vibrator in and out of her pussy. She said she'd never had such intense orgasms.

"All these years I've missed out on great sex because of being too uptight. What a shame," she said.

But whenever we'd get crazy enough to try pure anal sex with my cock, it would always be too painful for her and would turn out to be more agony than ecstacy. Midway through, we'd give up and move on to more traditional sex.

One day when I walked through the door from work, Jennifer called for me to come upstairs.

Standing near the bed with a hot neglige on, she said in a low voice, "I have something to show you that I think you'll like."

She turned around and lifted her neglige and bent over to show me the surprise: protruding from her ass was a red butt plug. She gently touched its base.

"I've had this in all afternoon. I put it in with lots of lubricant and every now and then I move it in and out. It really works. Now it feels good and I've already had an orgasm playing with my myself. I want you to fuck my ass. It's ready."

Without any further encouragement, I stripped and gently pulled the butt plug out.

"Play with it a little," she whispered. "It's about the same size around as your cock. I want my ass to be ready to take all of you."

On the bed with her on her knees, her sizable ass sticking out, I gently moved the butt plug in and out.

"That's it," she moaned. "Nice and slow. God, it feels so good. I never thought . . ."

Then she was ready.

"Get the lubricant out and put lots on your cock and in my ass. That's it. Now fuck my ass, nice and slow."

I did as instructed. I slowly entered her asshole, sticking the tip in and gently moving it in and out. Her ass was tight, but not like before. It gave and soon I was gently entering her nearly all the way. It was all I could do not to come immediately. It felt tighter than her pussy but not so tight that I couldn't handle the overwhelming sensation. I held on and didn't come.

"That's it," she said over and over. "Oooooohhhhhh! Do you like it? I'm so turned on. Put it all the way in. Now go a little faster. That's it."

Soon I was pounding her ass, as if it were regular sex. She moaned and begged me not to stop. Then she began furiously rubbing her clit and started screaming like she never had before. I grew paranoid the neighbors could hear but soon forgot about it. After several minutes, she came and I could feel her thighs shiver and her asshole tighten. It was incredible. I came in her ass about a minute later and we both collapsed in a heap on the bed.

"I've never had an orgasm like that," she finally said. "I felt it everywhere in my body. I can't believe we've never done this before, I mean all the way."

After that, we went from having sex once or twice a week to nearly every other day. I wish I could say anal sex always played a role, but it often did.

One night, after lots of foreplay on the massage table and lots of wine, she wanted me to insert a regular sized dildo into her ass while she fucked me on top.

In the middle of this, she said, "I know I've had lots of wine, but too bad we don't know anyone who can enter me from behind while you’re inside me."

All I could say was, "You never know."

It turns out I did know someone who would satisfy her new fantasy. Bob was an old college friend of mine who had just gone through a messy divorce. He was dating every now and then but was obviously horny. He has always liked my wife, and every now and then I could see his eyes moving up and down her body. Then one day, after a night of drinking, he confided in me that he and his younger cousin had double teamed on an old girlfriend years before, just after graduating from college. He told me all the details: they started by getting drunk and engaging in sex talk, each person sharing a fantasy. Bob always suspected she'd try two guys at once but was too embarrassed to talk about it. When it came time for her to share her fantasy, she said she always wanted to have sex with two guys.

After that it wasn't long before the three of them were on the couch making out. They soon had her top off and were playing with her breasts and nipples at the same time. In bed she let Bob enter her from behind while she sucked off the cousin. She moaned and groaned and had a huge orgasm, but afterward was embarrassed and the three never had sex together again.

I never actually heard a real person relate a real ménage à trois story before, but I believed every word of it.

"You know," I said, "if we play this right, we can do the same thing with Jennifer."

Bob's eyes grew wide and he said, "Really? Jennifer? Is there something you're not telling me?"

Bob and I had never discussed our sex life in detail before this night, but I told him everything. He said I was lucky to have a wife who still experimented in bed and would try anal sex without any hang-ups. He was intrigued by her double penetration fantasy.

"So, how do we do this?" he finally asked. "I really can't see Jennifer actually letting me do this. How do you feel about this? Would you be cool with it?"

I assured him I would. Why else would I bring it up? We decided then and there that next weekend he would come over for dinner and see we'd see what happened.

The following Friday the three of us had a fabulous tri-tip dinner at my house, starting out with margaritas and ending with wine. Jennifer was loose and talkative and seemed especially happy to see Bob. In the living room Bob and I discreetly lead the conversation to sex. At first Jennifer seemed turned off to the subject, but after Bob shared his experiences with sex, or lack of it, with his ex-wife, she got interested and we got on the subject of fantasies. Bob said his was to have sex with a stranger on an airplane, and I said I always wanted to fuck my wife at her parents' house in their living room.

Then we both turned to Jennifer and I asked, "How about you, Jennifer? What's your fantasy?"

A panicked look spread across her face and she finally said, "I really can't say."

"Oh, come on Jennifer," I said. "Bob is a friend. We're all being non-judgmental here."

With a knowing look on her face, she said, "I know you've already told Bob everything, so I might as well tell him. My fantasy is to have two guys at once. Okay, I said it, now onto the next subject. Not all fantasies are meant to come true."

With that she got up to open another bottle of wine and it seemed the topic was closed.

But a little while later Jennifer asked Bob a question out of the blue that floored both of us: "Have you ever had a ménage à trois, Bob? I'm sure you have. You've done everything."

Bob said yes and told her about his experience with his younger cousin and the ex-girlfriend.

"So that's what this is all about. You guys planned this whole thing, thinking something was going to happen."

We said nothing and waited for her to go on.

"Okay," she said after several uncomfortable moments. “I’m just drunk enough to try this. But if I want to stop, we stop, okay?”

We both nodded our heads enthusiastically.

“Where do we start?” Jennifer asked. “Bob, you’re the expert. Tell us what to do.”

“Well, why don’t we all sit together on the couch with Jennifer in the middle,” Bob announced.

Soon we were huddled together side by side on the big couch, and I took Bob’s hand and placed it on Jennifer’s thigh. I kissed her and then told her to kiss Bob. Before I knew it, she had Bob were French kissing and she began to get into it. I knew I had her.

After that, it all unfolded nearly without a word. I pulled Jennifer’s top off and unhooked the clasped on her bra. Jennifer’s breast are enormous, not exactly perky after 33 years, but with large, protruding nipples. I took the right breast into my mouth and began to role my tongue over her nipple and gently bite. Bob took the other breast and soon Jennifer was holding both up and softly moaning.

I stood up and took Jennifer’s hand and lead her and Bob upstairs. In the bedroom, Jennifer said for us to wait while she changed.

“I think you two know what to do,” she said and went into her walk-in closet and closed the door.

I looked at Bob and asked, “Do we take off our clothes?”

“I guess so,” he said.

Oddly enough, this was perhaps the most awkward thing about the whole evening. I had seen Bob naked many times as roommates in college. He had the habit of leaving the bathroom door open while he blow-dried his hair without a stitch of clothing on. He had a firm body and a long, somewhat thin cock. I never let him see me naked since he had 2-3 inches on me. My only consolation was that my penis was thicker.

But that night, emboldened by the wine and the prospect of something totally wild, Bob and I both stripped and lay on the bed naked, with all the lights turned off but the one in the hallway. Jennifer finally walked in wearing a short negligee and stopped, looking at the two of us as she gasped.

I got up and led her to the bed, letting her lie between Bob and me. I ran my hand up her thigh to discover she had no panties on underneath her negligee. She began to breathe heavily as I found her clitoris and gently rubbed it. I looked at Bob and motioned with my head for him to do something. He began to caress her breast and leaned over and kissed her. Jennifer was getting wetter and wetter and began to softly moan.

When I began to pull her nightie up, she said, “No, leave it on.”

“Jennifer, I said, “Bob and I are totally naked and you should be also.”

“Okay,” she said softly.

Again, Bob and I went to work on her breasts and nipples while I played with her very wet pussy. I took Bob’s hand and placed it there and he inserted his finger into her. She moaned more loudly and soon Bob was working two fingers in and out of her.

I placed Jennifer’s hand on Bob’s growing cock and whispered in her ear, “Get him nice and hard.” I was enjoying myself as director of this whole experiment.

She touched Bob’s cock and slowly began to stroke it.

“Faster,” I told her.

She went faster.

"Now I want you to put him in your mouth."

But she rolled over and took my cock into her mouth. I let her suck on it for a short while and pulled her head away.

“Now do it to Bob,” I said. “He’s getting lonely.”

She rolled over and looked into his eyes and then looked at his semi-hard cock. Then she quickly bent down and began to suck on him, at first gently and then furiously.

I let her go at it for a while as Bob breathed heavily and began to encourage Jennifer.

“Yes, Jennifer, keep sucking,” Bob said. “It feels so good. You’re incredible.”

Then I pulled Jennifer up to her knees, telling her to keep sucking Bob. Both she and Bob positioned themselves more smoothly than I thought was possible and I had Jennifer’s ass in the air as she continued to suck on Bob’s cock, her head between his spread legs.

Standing up, I worked Jennifer’s pussy with my finger until it was wet again and slowly entered her from behind. She jerked and moaned and sucked on Bob’s cock at a more furious pace.

I was pounding her so hard she was having a hard time keeping Bob’s long cock in her mouth.

Suddenly I stopped and said, “Get on top of Bob, Jennifer, while I watch.”

She hesitated and looked up at Bob.

“It’s okay, Jennifer. Please do it,” said Bob.

Without any more encouragement, she moved up and over Bob and grabbed his cock and put it slowly inside her. She gasped and began to breathe heavily, moving up her ass up and down rhythmically.

Bob is six inches shorter than me in height, which is perfect because my wife’s big tits hung perfectly over his face. He instinctively grabbed them and caressed both nipples, which were as hard and as protruding as always. I suddenly felt immense pride in my wife’s voluptuous body and stared in amazement as they both fucked harder and harder.

I positioned myself at the end of the bed and watched Bob’s long cock go in and out of her pussy, from the tip all the way to the hilt. I couldn't believe how much it turned me on to watch another man fuck my wife.

“Do you like this, Jennifer?” I asked.

After a moment, she said lowly, “Yes.”

“Then make some noise, it’s okay.”

She began to moan, at first quietly and then all of sudden she let herself go and began to get louder and louder. I put some lubricant on my finger and came forward and worked my finger into her ass gently as Bob slowed his pace. I knew this would set her off.

“Oh, my god!” Jennifer yelled. “Yes, yes, yes. Don’t stop.”

Soon I was working my index finger in and out of her asshole as she rode Bob up and down. Every now and then she would pound so hard my finger would slip out, and she would slow down and grab my hand and put the finger back into her asshole.

After a several minutes she said, “I’m going to come. Don‘t stop. Keep going.”'

Her orgasm was long and loud. All she could say was, “Please don’t stop”, over and over, and her whole body quivered and I felt her ass tighten as she had an intense orgasm.

She looked into Bob’s eyes and asked, “Did you come?”

“Yeah, a little while ago.” He responded.

Suddenly she was off Bob and off the bed, heading straight toward the bathroom. She closed the door and Bob and I looked at each other expectantly.

After several minutes, I went to the bathroom door and asked, “Jennifer, are you okay?”

No answer.

I repeated my question and she finally said, “I’m fine. Bring me my negligee and get in bed, with Bob if you want.”

Bob and I did as instructed and soon Jennifer walked back into the room with her nightie on and got in bed between Bob and me.

After several minutes of silence, Jennifer said, “That was incredible.”

I sighed in relief and Bob laughed and said, “We thought you were upset.”

“No, a little embarrassed, I guess. But I have no regrets.”

I got up and announced I would be right back with another bottle of wine. It's just after ten p.m. and I wanted to keep the party going.

“Why don’t you two snuggle while I’m gone,” I said.

Jennifer rolled her eyes and turned over to face Bob.

When I returned with a bottle of chardonnay and three glasses, she and Bob were talking quietly but had not touched each other. I guess they felt they needed my presence before going any further.

After we finished the bottle Jennifer fell asleep while Bob and I crept downstairs to talk. We were both wired.

“That was truly an experience,” I said to Bob.

“Do you think she’ll let us do it again?” he asked.

“Let’s go upstairs and find out. But give it a while.”

About half an hour later I heard Jennifer walking upstairs and went up. She had gone to the bathroom and was back in bed.

“Where’d you two go?” she said.

I told her that she fell asleep and that Bob was still here.

“Tell him to come up, with more wine. I want to talk to you guys.”

Bob meekly came into the room. We were both wearing bathrobes.

“You brought your own bathrobe?” she said to Bob, with a hint of irony.

“Uh, yeah,” he murmured.

“It’s okay,” she said. “I guess I kinda expected this.” She looked at me. “Are you really okay with Bob and I, you know, doing this?”

“Absolutely,” I said. “It totally turned me on.”

She just nodded her head.

“Get in bed, you guys,” she said with a glint in her eye.

Again we found ourselves in bed, leaning on our elbows as we sipped wine. Again, Bob and I were naked while Jennifer still had her nightee on. I put down my glass and suddenly kissed Jennifer.

“Round two?” I asked.

She just nodded her head.

This time around we felt more comfortable with ourselves and moved more naturally, without hesitating.

Again, I encouraged Jennifer to mount Bob and soon they were going at it. Again, I stuck my lubricated finger in Jennifer’s ass as she positioned it up, beckoning me again.

After a minute she turned her head and asked me, “Do you think you could get inside me, you know, back there while Bob is inside me?”

Bob looked up and I could see the amazement in his eyes.

“I’ll try,” I said.

I had seen double penetration many times in porno movies, and the pros make it look so easy.

But for us amateurs, it took a lot of directing and repositioning from Jennifer before we sort of got it right. With Jennifer on top of Bob, she closed his legs and I moved over them, straddling them. Jennifer had her ass high enough for her to guide my cock and place it on her tight opening. I frantically poured half a bottle of lubricant onto my cock and worked some into her asshole as she put Bob’s cock back into her pussy.

Because his cock is so long he could fit half of it inside her while she positioned her ass up.

She gasped as my tip entered her asshole and she said, “Be gentle. Go real slow.”

Soon I had worked half my cock into her asshole as Bob lay motionless. Jennifer moved her ass up and down gently as she kept both of us inside her.

“Move in and out a little faster,” she said.

“Who?” I asked.

“Both of you,” she said.

With that, we both pumped faster and I could feel Bob’s cock moving in and out on the other side of Jennifer’s thin sphincter muscle. At first Jennifer moaned lowly and then began to pant, breathing harder and harder.

“Is it okay?” Jennifer, I asked.

“It hurts a little. But don’t stop.”

After several minutes we hit our stride, and as Bob entered her pussy all the way, I would gently pull out until we were alternating our penetration, like slow moving pistons. This sent Jennifer over the edge.

“Yes, yes, yes. Just like that. Oh my god, it feels so good. Don’t stop, don’t stop.”

Then she grew quiet and breathed hard. Bob never said a word.

As is my way, I began to talk. “You like both of us inside you, don’t you Jen? You like your holes full of cock?”

“God, yes,” she moaned. “Don’t stop, don’t stop. Please, please, please.”

Suddenly I couldn’t control myself and was about to come. I wanted to pull out to make it last but couldn’t stop. I came inside her and she must have felt the hot semen because she moaned louder. I kept moving my cock in and out of her beautiful ass, my come acting as an even better lubricant. Within a minute it was Jennifer’s turn.

“I’m gonna come. Don’t stop. Don’t stop. Please don’t stop.”

As she came she let out an ear-piercing scream and again I could feel her body shudder and her asshole tighten. She pumped furiously for another fifteen seconds until she was spent and said, “Okay” and rolled off Bob.

The three of us were sweating and breathing hard. After several minutes, Jennifer turned to Bob and asked, “Did you come?”

“No,” Bob said, “too much wine, I guess.”

I gently pushed Jennifer over to Bob and said, “Please finish him off. Show him how good you are.”

Jennifer moved down the bed and took Bob’s cock expertly in her mouth. Bob quickly looked at me and then away. I’m biased, but I think my wife gives the best head around. She grabbed Bob’s testicles and squeezed hard as she alternately sucked and licked his shaft.

As I watched Jennifer suck Bob’s long cock furiously, I knew we had turned a corner in our sex lives that we would never go back from. Bob moaned more loudly now as he came closer to orgasm. Suddenly he grabbed Jenn’s head and thrust forward, coming into her mouth.

After that three of us had sex many times together, until Bob married a woman who was too conservative. Bob never told his new bride about our tryst and never expected her to join. Every now and then Bob, Jen, and I get together for some fun.