Jan's Big Night with Tory

My girlfriend Jan and I had been together for about five months. It was a relationship I wasn't all that enthused about being in, but it was OK for me at that time. Basically, I was getting pussy on the regular and didn't have that much invested emotionally.

Let me give you a little bit of back story.

She was six years older than me. Despite not being a classic beauty, Jan walked around as if she was the hottest thing on the planet. She often dressed like an 18-year-old rather than the 40-year-old woman she was. Don't get me wrong, she was an attractive woman but she wasn't all she thought she was. She was fairly pale, a 5-foot-6 freckled redhead with shapely legs and a real onion for a butt. Jan loved going to the gym. She didn't have big breasts, but I was more of an ass man anyway.

Me, I'm a 34-year-old black man with an average build. I keep myself in shape by riding my bicycle and long walks. I'm not a gym rat, so I'm not a muscular guy, but I'm satisfied with my physique.

We had met at a friend's Fourth of July party a few months earlier and seemed to hit it off pretty well.

We had dated for a few weeks. Though we hadn't slept together at the time, things seemed to be going well before she suddenly broke things off. Jan left a message on my phone telling me how she had a boy toy she was unwilling to give up and that she also was seeing a sugar daddy who could support the type of lifestyle she wanted.

I thought simply leaving a message was a bullshit way to end things, but like I said, I wasn't emotionally invested. I didn't even call to ask for more of an explanation. I simply just let it go.

One night I walked into my favorite hangout to hear my friend's band play. And there Jan was, sitting with a guy named Clarence, another black man whom I'd known for a long time. I walked over to their table, said hello and chuckled as I walked away.

I genuinely felt nothing and didn't give either a second thought. I danced with several other women that night and ended up having a one-night stand with a woman named Denise, but that's another story.

Anyway, two days later I got a call from Jan. My initial thought was to simply hang up on her but I decided to hear her out. She was apologetic about the way she ended things, and told me that she'd broken up with both her boy toy and sugar daddy.

"So, what does any of this have to do with me?" I asked.

She told me how much she enjoyed our short time together and realized we had a chance for something real and wanted to try again. Because she was on the other end of the phone, she couldn't see me roll my eyes. I let her know I wasn't interested. When she asked why, I reiterated she a boy toy and a sugar daddy, which puts me in third place. And I'm not anyone's third choice, then I ended the call.

Jan, however, was persistent and kept pursuing me for the next three weeks. Finally, I agreed to go on one date with her. We wound up having a good time on the date and had a rousing night of sex. And we continued to date and have sex.

One night were lying in bed one night and she was lamenting how one of her friends, Nancy, was so depressed and lonely. Nancy had broken up with her boyfriend more than a year ago and had not been with a man since. And for some reason, no man had shown any interest in her, which was odd because though she wasn't drop dead gorgeous, she was attractive.

"Dan, do you have any single friends who might be interested in going out with Nancy?" Jan asked.

"I know a couple of guys," I said. "It depends on what she wants. If she's looking for a relationship, I could set her up with my friend Mitch. If she just wants her brains fucked out, I'll hook her up with my friend Tory."

She asked about each guy. I told her Mitch was a nice guy, average looking...not too outgoing but a solid guy. I told her Tory wasn't exactly a one-woman man, to say the least. I mentioned that Tory was into the swinging lifestyle.

The swinging lifestyle seemed to pique her interest in Tory. She peppered me with questions about him, such as his build, his age, where he hangs out. She asked if I ever participated in any swinging with him, and I was honest and told her I did a couple of threesomes with him. Finally, she asked the question I knew was coming, which was about the size of his equipment. All I said was he's not small at all and left it at that as I rolled over to try to sleep.

About 10 minutes later, Jan cuddled up to me, began fondling me and asked exactly how big Tory is. I said I've never measured his cock, so I wouldn't know.

"Well, compare him to you," Jan said. I was honest. I told her that he was about an inch longer than me and a little thicker than me when I'm hard and he's soft (I'm about 7 inches when hard). That drew a little gasp from her. I finally went to sleep, but when I woke up a little later, I saw her rubbing one out. I smiled, shook my head and went back to sleep.

The next evening as Jan and I were cooking dinner at her place, and unexpectedly I got a call from Tory asking if he could borrow a little cash. I asked Jan if it was OK if he came by so I could loan him money. If not, I'd go meet him somewhere else if she was uncomfortable with someone she wasn't familiar with knowing where she lived.

She said it was OK. About a half hour later, Tory knocked on the door. My intent was to just answer the door, hand him the money and send him on his way. But Jan's curiosity got the best of her and she came to the door as well. She immediately invited Tory to stay for dinner.

Tory is as tall as me but quite a bit more muscular, as he is a gym rat who works out four times a week. He was wearing a baggy pair of shorts and a very loose-fitting T-shirt.

We were dining on the back patio and went through a couple bottles of wine. I noticed Jan sneaking peaks at Tory's crotch area. He caught her a couple of times too. But his shorts were so loose she could not get a good look at what he was packing. Jan cleared the table and went inside.

Tory asked if she knows he's a swinger. I said she knows, and she also knows you're not a small guy. I said if you want, give her a little bit of a show and let's see where this one goes. He asked if I'd be mad. And I told him my true feelings about our 'relationship.'

He then went to the bathroom to make some 'adjustments.' Jan was back in her chair when Tory returned. Jan's eyes immediately went to his crotch and so did mine. I saw he had aroused himself and the outline of his cock became much more visible. Her eyes were fixated on what was swinging back and forth in his shorts, and she was crossing and uncrossing her legs nonstop.

Tory went to the kitchen to get a glass of water, and Jan leaned over and asked if I had planned this night. I told her I had not, which was the god's honest truth.

"My God, that thing looks so fucking big," Jan said. "I just want to see it. Damn, I can't believe how wet I am right now just by looking at it." When Tory returned to his seat, Jan made no attempt to hide her interest. She again focused her eyes on his crotch area and was licking her lips.

Tory shot me a look, and I shrugged my shoulders. He took that as a sign to go further. He then stood up and took a couple steps closer to Jan. He looked down at her and told her she has his permission to touch it. She didn't have to be told twice. She reached out with both hands and began massaging his cock through his pants. Her breathing got heavier and heavier as she continued to stroke him.

I suggested that maybe we should take this inside to the bedroom. Jan was so excited she damn near ran into the bedroom. Tory and I looked at each other and burst out laughing. It was as horny and excited as I'd ever seen Jan. By the time Tory and I got to the bedroom, Jan had shed all her clothing and was on the bed on her knees waiting for us.

Tory again asked if I was OK with all that was going on, and I told him that it was her night. He told me he was going to make her see God. Tory then began to undress. First the shirt, then the shoes and socks and finally he dropped his baggy shorts. He was down to his boxer shorts, which were bulging out because by this time he was harder than a horseshoe.

He stepped in front of Jan and told her to do the honors. Jan looked over at me as if seeking my approval. I winked and nodded. She then reached up and slowly tugged at his boxers until her prize was revealed. There Tory stood, naked in all his glory with his hands on his hips. Jan's eyes seemed like they expanded to the size of saucers, and her mouth was agape.

"Uh-oh," Jan gasped.

"Something wrong?" Tory asked.

"No, nothing's wrong. This is...it's just...my god you're just so fucking huge, and I've never had anything like this before," Jan said breathlessly. "Damn...so fucking big."

She reached up with both her hands and was caressing that massive dick and still had a look of amazement on her face. She licked the tip to taste some of the pre-cum and tried to put it in her mouth. Her efforts were in vain, as all she could fit in her mouth was the head of his cock.

I thought about undressing and joining them but I figured I'd just let Jan enjoy this one for herself.

Tory then pushed Jan on her back, spread her legs apart and started licking her pussy.

"When you've got a big dick, you've got to lick pussy well," he said. "Got to get that shit wet enough for me to fit all this in."

Jan was clearly loving the way Tory was eating her out, as she was gripping the sheets. Her moans were getting louder and louder and her head was tossing from side to side. She was bucking her hips into his face with wild abandon.

"OH FUCK. YOU'VE GOT ME," she screamed. "OH MY GOD...YOU'VE GOT ME. OH FUCK...I'M GONNA CUM. OH I'M GONNA CUM." She looked as if she were having a seizure when she came so hard.

She was still shaking when Tory told her the real fun was about to begin. He licked his way up to her breasts and then the two engaged in a deep, long kiss.

"Do you like how you taste?" he asked.

"Oh fuck yes," she said.

Tory reached down and began rubbing his huge cock head up and down her slit. She was bucking her hips trying to get him to put it in her. He stuck the head in and began teasing her with it. Finally, with such desperation in her voice, she begged.

Tory slowly worked inch after inch into her tight pussy and Jan couldn't help but moan and grunt. Jan wrapped her legs around his back, and as he kept going deeper into her pussy, she was digging her nails into his back.

When he finally got all of it inside her, he just held it there so she could get used to having such a gigantic cock inside of her. He lay still but she was squirming, rotating her hips and sliding her feet up and down Tory's calves. He asked her if she's ready to really get fucked. All she could get out was a soft "uh-huh."

Tory began pummeling her pussy with short strokes and she was whimpering and moaning each time he pushed into her. After a couple of minutes, he started hitting her pussy with deep, longer strokes, which drew even louder, high-pitched moans. The headboard of the bed was slamming into the wall so hard I thought it was going to bust a hole in it.

Jan looked as if she was in another dimension as her eyes rolled to the back of her head while her hips were bucking to match Tory's strokes.

Tory then said, "fuck this," and then pulled Jan to the side of the bed. He then snatched her legs into the air, placed her legs over his shoulders and really started to slam into her with abandon and no regard for the state of her pussy. By this time she was screaming at the top of her lungs. She was grasping at the sheets, her head thrashing about.

"OH GOD TORY, you're so fucking big. YOU'RE SO FUCKING BIG. OH MY GOD. I'VE NEVER BEEN...OH FUCK...OH MY GOD...AHHHH. I'M GONNA CUM AGAIN. I'M GONNA...UUUUUGGGHHHHHH.

Jan came so hard, her orgasm so intense tears flowed from her eyes. Tory had tremendous stamina which probably came from working out so much and still wasn't done. With his cock still deep inside Jan, he picked her up off the bed, and fucked her standing up. All she could do was hold on for dear life as she moaned and screamed into his shoulder.

When he was finally ready to come, he placed her back on the bed and with a loud growl unleased a flood of his seed deep into her womb. When he finally pulled out, a gush of his come leaked out from her pussy. He then straddle her and stuck his cock right in her face, as if he wanted her to lick him clean of both their juices. But Jan grabbed his semi-hard cock with both hands and caressed and stroked it for about a minute as if she was applying lotion to a forearm.

Finally, she covered his cock with kisses, and licked the bottom of his shaft and thanked him for fucking her like no man had ever done.

He then got up, went to the bathroom to clean himself up. I looked at Jan on the bed, her eyes had a glazed look to them, and her legs were splayed open with Tory's juice still leaking from her gaped open twat. Tory got dressed, gave me a high five and left.

For me, it was like a porn video coming to life. Jan was so sore apologetically she said she wouldn't be able to fuck for a couple of days.

Jan and I didn't last much longer after that night, but that fuck scene is in my memory bank forever.