A Gal Friend Stays the Night

A GAL FRIEND STAYS THE NIGHT

Sex with Tom lets a friend remember her sexy past

Somewhere in her 40's Eileen had become a widow. We lived in different parts of the country yet she had kept in touch with my wife Valerie and me. Now living in Wisconsin she was going on a three week Mediterranean trip and was flying out of Chicago. In a phone conversation she mentioned what a pain that departure point was for her as it led to hotel and car parking expenses but she had no choice. This would amount to almost $600.

My wife offered up an idea. Since we had a small summer cottage just outside of Chicago she suggested using our place as a parking space. Just a taxi ride to O'Hare and back again would really save some money. Plus, the car would be safe in our garage.

I was scheduling a trip up there around that time as the place was in winter shut down condition and was due to be opened up. This would save her a hotel bill as well. So, more than pleased and grateful at the travel benefits with our plan, it was a go. I would get up there a couple of days before her arrival.

Eileen got to our place midday and I was reminded of her good looks. A little older than me in her early 50's but still fit and slim as she keeps up her exercise activities, eats right, and generally takes care of herself. Probably 5'8'' and maybe 125 pounds she looked athletic and vital. This wasn't your typical widow; Eileen was mature, not elderly, and she was attractive.

After we set up her car storage and worked out a schedule I took her to one of my favorite Mexican restaurants here in our town. A nice quiet place, not the noisy family restaurant atmosphere that is so common. We sat in the bar area and knocked off a pitcher of Margarita's before we even ate.

After an hour of very friendly reconnecting we headed back to my cottage. This place is small but cozy. As a couple my wife and I visit Chicago several times a year with an additional long summer vacation and this place serves as our secondary abode.

However, it only has one bedroom. The house is only 800 square feet. I planned to let Eileen use the bed and I would hit the couch. The one problem is that the "couch" is really a small loveseat. I have never slept in it and there was a question as to whether it would be large enough for me to stretch out.

It was as we were sitting in this loveseat having a few after dinner beers that Eileen asked where her bedroom was. It is obvious that there are only two rooms. I told her that she has the bedroom and I planned to sleep "right here".

She objected and demanded that I take my own bed as she could certainly sleep "out here".

"You have already helped me so much. I can't take your bed."

A little discussion followed but I put my foot down telling her she won't win this as I am going to strip down and "hold the fort".

It was 10 PM and we were both a bit tipsy. I got my blanket and pushed her into the bedroom. I got a big hug with her arms around my neck and a pretty surprising goodnight kiss. A real kiss. Nice. Probably the alcohol as there was no hint of seduction.

Unfortunately, I was miserable in my sleeping choice. I'm only 5'11" but I could not stretch out. Without fitting properly I tossed and turned. It was midnight and I was still not comfortable enough to sleep.

Somehow, Eileen must have become aware of my plight as she surprisingly stood before me holding a pillow at her front to cover herself. It was quite sexy as the pillow just barely covered her breasts and her privates. Just enough light coming in from an outside street lamp illuminated her form.

She asked if I'd had enough, that it was time to switch with her. She could handle the loveseat. I mentioned that she is about the same size as me so why would that work?

"Okay", she said, "Come to bed and we can both get some sleep. I won't mind."

I really liked the idea. It was practical for one but I also was thinking that sleeping with another woman is really kind of exciting. My wife is 1500 miles away, I've had a few drinks, and this gal is tantalizing. "Okay, deal."

Here, she turned to go to bed into the other room but absentmindedly kept the pillow in front thus exposing her backside to my view. She was nude! No bra, no panties, just a bare little ass swishing thru the mostly dark room.

I waited a few moments as she got back into bed. I stayed with the jockey shorts I was wearing thinking that it would be best for a little self control. I was mindful that she did not come on to me, just thoughtfully offered a sleeping spot.

Believe it or not I did get to sleep. With a safe space between us in our queen size bed there was no contact. However, I was quite aware of her femaleness just two feet away. For one thing, I could smell her. The luscious scent of femininity.

Well into the night, sometime before dawn, I awakened to a gentle rocking. Eileen was masturbating. The sheet was moving down around her crotch as her hand was at work. Once again, the street lamp gave just enough light for me to see the activity. She was nowhere near a climax as her breathing was calm but this was really erotic. I stealthily watched this as I did not want it to cease.

However, I had been detected. Eileen spoke in a low tone, "Tom, are you awake?"

I answered, "I just woke up. I hope you are not going to stop."

With that, I lifted up and put my hand over her fingers that were still resting on her mound. I held it there and told her not to be embarrassed, that it was alluring and beautiful. I continued holding her but I also started moving our hands together smoothly over her pussy. She went along with this for a time but then she slid her hand away and left me in that place.

Now I was touching her and feeling her wetness. My finger went inside up to my knuckle and I held it there with only very small movements, not a full-on finger fucking, just a sexual entry with only slight brushes to her clitoris area.

After a few moments like this I lifted up and kissed her breast. She was amazingly responsive as she released several heavy breaths. Holding her like this I had an idea.

"Eileen, please trust me, I have a wonderful idea, something you might really enjoy." I left the bed and went around to the nightstand where Val keeps an 8 inch latex dildo she calls "Mr. Brown" because of it's color.

I swiped some lube on "Mr. Brown" and stepped back to Eileen, turning her body so she was lying on the edge of the bed with her feet dangling to the floor. I touched the dildo to her outer lips gently, holding it there almost for approval. She had not actually seen this substitute as I was in shadow but she knew there was a prick at her door.

A slow entry and now she knew she was being penetrated but she might have thought it was me at this point as I was standing between her legs. All the way in...and she gasped. Say what you will, a full 8 inches is a lot of cock to many women.

I shifted a little off to the side towards one leg so now she knew it was a proxy. But she was responding with vigor as her hips were moving with my thrusts. Long, deep thrusts with the recognizable rhythm of fucking.

My position beside her legs was that of a pumping sex machine. As she exploded into orgasm Eileen grabbed my hand and squeezed tightly. When she calmed down I slowly withdrew the stand-in prick and stepped back.

She let out a spirited, "Whew! What wasthat? I need to see him."

I turned on a small table lamp and showed her the dildo. "His name is Mr. Brown and he sometimes takes care of Val."

"Gawd....what a hunk!"

Me: "I often wondered if it felt like a real prick to a woman, you know, warm and such. Alive."

Eileen: "Tom, I was really into it as you might have noticed. I thought you were doing me at first and I really didn't care what the hell was going into me, I just liked it."

She followed with, "Maybe you should give me a sample of yours so I could decide what works best? I'd love a real screwing right now. I'm still wound up and could take a 'second' man."

Although I hadn't expected this offer I was also "wound up". My prick was iron-hard, jutting out from my undershorts in a most obvious way. I took quick action to pull them off and stepped closer to Eileen who was still at the bed's edge.

Pulling her to me I lifted her legs to my shoulders and entered her smoothly, deeply, all the way in one thrust. The ample dildo had opened the pathway plus Eileen was quite wet and slick from the lube and her arousal.

With my prick buried into her she gasped, "Wow! That's a real one."

This caused both of us to laugh a bit at her remark with me adding, "Watch out, this one also squirts."

We shared a really nice coupling at first but it soon became an enthusiastic banging. Though tonight was a surprise for both of us we were sexually charged and it showed Eileen climaxed excitably before me with a "yes...yesss" while I came into her seconds later. It was just a few minutes, maybe ten; short but very hot.

As I withdrew my sex partner told me, "That warm prick feels better. It's the real thing and a gal can tell the difference. Plus, that squirting is important. A woman likes to feel that, at least this woman."

We cleaned up a bit and I settled over in my sleep spot. Eileen moved over and gave me a big kiss. It was a thank you kiss, a post-loving kiss. It was understood completely.

"Eileen, what were you thinking about when you were masturbating?"

"Well, I was laying naked in bed with an attractive man to start with so it was easy to fantasize something sexual. I was envisioning me giving you a blow job. I was sucking your cock."

"Damn! That's pretty wild. I never knew you had these kind of thoughts."

"Tom, there are lots of things you don't know about me. You know, that thing we did tonight with 'the second man'? Well, I really had a second man experience once with Bobby and his old college buddy who was staying with us one night. We were in our late thirties."

"We got pretty drunk and the two guys took me to our bed. Bobby fucked me while his friend, Tim, stood at the bedside with his hard cock in his hand. I knew he was going to do me after Bobby and itreally turned me on."

"Sure enough, when Bobby blew his load Tim mounted me and took me to an orgasm. But it wasn't over as my husband went back at me and I got off again.

"It was a wild night, kind of a mini-gangbang, as the boys had me several times. I lost count as we fucked between periods of sleep. I felt like a slut but in a good way. I was a hot woman that was satisfying her men, any man that came to her. I was insatiable for cock and I was orgasmic over and over."

"What started as a drunken moment of lust turned into a most amazing sexual experience, an unforgettable experience."

Me: "Wow! What a hot, sexy story. Were you thinking of it tonight?"

"Yeah, Tom, I was thinking about it. You were standing there beside me, watching that prick go into me, watching it just like Tim watched Bobby. That's why I wanted you to follow 'Mr. Brown'."

"It was exciting for me to replay that sex-crazed night when my two lovers buried their cocks in me again and again, filling me up with their seed, making me cum over and over. I was in that bed for that purpose...to be fucked, and I liked it. Shit, I loved it."

Me: "Did you do anything like that again? Any more multiple sex partners?"

Eileen: "Nope, just that one time. We talked about it but it never happened again and then I lost Bobby."

This conversation had caused a very natural reaction to my prick as it was standing straight up. Eileen took note and grabbed the base before she engulfed as much as she could into her mouth. Several deep, wet slides followed by a swirling tongue to the cap was a finish to our sexy night. A sweet kiss on the crown was the closure.

Eileen: "There, I got in a little cocksucking, too. I might use that to prompt my next fantasy."

Her giving head at this time wasn't a serious approach as daylight was upon us and we needed to get ready for the trip to the airport. The sexual activities were over but she ended with a provocative remark.

"You know, Tom, we could do this again sometime. You and Mr. Brown would be welcome sex partners. Think about it, I know I will."

My very short time with Eileen ended when I dropped her off at departures. I went back to the cottage feeling pretty good about the whole thing. I found out a little about our friend's sexual history and I loved how she shared it with me. Plus, I got the anticipation of another possible hookup.

Her three-way excited me, especially the way she told it. I masturbated that day while laying over on what was earlier ground zero. I didn't wash the sheets as it carried her body smell for some time and I enjoyed recalling the episode.

Valerie was okay with the whole thing as she always understands sex opportunities. She especially liked Eileen's double partner story.

"She kept that kind of private, I guess. But good for her, she still has the hot memory even though Bobby is gone."

Meanwhile, I wonder why my wife keeps sending me into situations where I am alone with sexy women. Over the years she has practically farmed me out.

Author's note: with regards to the last paragraph, see "Travel Escort Has Benefits", "My Travel Partner Visits Sacramento","Mrs Wilson Next Door", and "Our Journey With Nicole"